Title: Holiday Rentals Winchester from £95: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Winchester Travel Guide](https://expedia.co.uk/Winchester.dx175481)[Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d175481.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d175481.Holidays-City-Breaks)

![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[27 Mar - 29 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[24 Apr - 26 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester holiday rentals

![Lobby lounge](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/a3189863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/6a31a5cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/8bc05b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Studio | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/62688d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Global Luxury Suites Downtown Boston

[](https://www.expedia.co.uk/Boston-Hotels-Global-Luxury-Suites-Downtown-Boston.h22788576.Hotel-Information)

Chinatown

8.0/10

Very good

(655 reviews)

"Everything was great about this place! I will definitely be staying here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amanda

£95

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Global-Luxury-Suites-Downtown-Boston.h22788576.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/2e7614de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/978ddac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/7f1f7cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/786b697a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 245 Newbury St

[](https://www.expedia.co.uk/Boston-Hotels-245-Newbury-St.h89756238.Hotel-Information)

Back Bay

8.2/10

Very good

(157 reviews)

"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Steven

[](https://www.expedia.co.uk/Boston-Hotels-245-Newbury-St.h89756238.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/0dd63623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio (Unit 7) | Terrace/patio](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/44b2972c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/05b3d150.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio (Unit 7) | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/2fc6bbd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 40 Temple St

[](https://www.expedia.co.uk/Boston-Hotels-40-Temple-St.h89660519.Hotel-Information)

Beacon Hill

7.6/10

Good

(103 reviews)

"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Jordan Elizabeth Marie

[](https://www.expedia.co.uk/Boston-Hotels-40-Temple-St.h89660519.Hotel-Information)

![1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/c0328429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment | Private kitchen | Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/5c22409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/f8b6e982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 1 Double Bed with Sofa bed | Private kitchen | Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/342a0357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Temple Place Suites

[](https://www.expedia.co.uk/Boston-Hotels-Temple-Place-Suites.h45791512.Hotel-Information)

Downtown Boston

7.0/10

Good

(331 reviews)

"Pretty clean room, good location, resonable price."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Beiyu

£122

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Temple-Place-Suites.h45791512.Hotel-Information)

![42-inch TV with satellite channels](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/f70f107d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![42-inch TV with satellite channels](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/bbc07a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/6bdc1239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, stovetop, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/b309a2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 400 Columbus Ave

[](https://www.expedia.co.uk/Boston-Hotels-400-Columbus-Avenue.h88179829.Hotel-Information)

South End

7.2/10

Good

(135 reviews)

"everything was great! only thing i’ll say is that the dots have some cracks where people can see in on the bathrooms and some rooms, but other than that i’d start here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maelynn

[](https://www.expedia.co.uk/Boston-Hotels-400-Columbus-Avenue.h88179829.Hotel-Information)

![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125080000/125077200/125077200/e6a316f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/126000000/125080000/125077200/125077200/5458ec70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/126000000/125080000/125077200/125077200/3ecf66a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/126000000/125080000/125077200/125077200/3ba10244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boston Financial District 1BR | Walk to anything!

[](https://www.expedia.co.uk/Boston-Hotels-Boston-Financial-District-1BR-Walk-To-Anything.h125077200.Hotel-Information)

Downtown Boston

£183

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Boston-Financial-District-1BR-Walk-To-Anything.h125077200.Hotel-Information)

![Premium Apartment | Living area | 24-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/2d8ce635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/w1438h1080x242y0-a59fde2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio | Egyptian cotton sheets, premium bedding, memory-foam beds](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/e514eb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment | Egyptian cotton sheets, premium bedding, memory-foam beds](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/677325f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chester Hotel

[](https://www.expedia.co.uk/Boston-Hotels-The-Chester.h105955992.Hotel-Information)

South End

8.6/10

Excellent

(28 reviews)

"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

kelly

£278

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Boston-Hotels-The-Chester.h105955992.Hotel-Information)

![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/55a7f850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/aa08e294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/41f2434e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/7e78cb5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bay Village Suites

[](https://www.expedia.co.uk/Boston-Hotels-Rooms-At-Premier-Suites-Bay-Village.h92422919.Hotel-Information)

Bay Village

6.6/10

(253 reviews)

"Great location nice neighborhood "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jose

£113

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Rooms-At-Premier-Suites-Bay-Village.h92422919.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/b68b988b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/2ec5ebb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/5e51303d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Room (2nd Floor - #209) | Individually furnished, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/6615076a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 28 Fenway

[](https://www.expedia.co.uk/Boston-Hotels-28-Fenway.h95348090.Hotel-Information)

Fenway–Kenmore

8.8/10

Excellent

(335 reviews)

"Good place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elijah

£151

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-28-Fenway.h95348090.Hotel-Information)

![Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/w851h480x0y0-8b426c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/w837h480x0y0-3c5d7594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room | Living area](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/1df69efb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/w843h480x0y0-ebedf864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premier Suites - Bay Village

[](https://www.expedia.co.uk/Boston-Hotels-Premier-Suites-Bay-Village.h76165648.Hotel-Information)

Bay Village

6.2/10

(257 reviews)

"We stayed there for four days. The heaters were not working, I got almost sick. And the customer service was awful. I hope you will find better place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aziza

£113

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Premier-Suites-Bay-Village.h76165648.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/58691629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/89de23c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/dcd26c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/a0975d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!

[](https://www.expedia.co.uk/Boston-Hotels-Charming-Private-1-Bedroom-Condo-In-Historic-Boston-Next-To-MGH-Hospital.h122591889.Hotel-Information)

Beacon Hill

10/10

Exceptional

(2 reviews)

"Had a wonderful stay! Beautiful condo in a beautiful neighborhood that is walking distance to the commons."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Grant T.

£200

includes taxes & fees

3 Feb - 4 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Charming-Private-1-Bedroom-Condo-In-Historic-Boston-Next-To-MGH-Hospital.h122591889.Hotel-Information)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/2be0a8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/bab50deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/62b779f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/31b86770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect One Bedroom Stay In Downtown Boston!

[](https://www.expedia.co.uk/Boston-Hotels-Perfect-One-Bedroom-Stay-In-Downtown-Boston.h103106122.Hotel-Information)

Downtown Boston

8.6/10

Excellent

(18 reviews)

"Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine

£171

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Perfect-One-Bedroom-Stay-In-Downtown-Boston.h103106122.Hotel-Information)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103120000/103113300/103113299/w719h480x0y0-36cdd484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, shampoo](https://images.trvl-media.com/lodging/104000000/103120000/103113300/103113299/5861dbb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103120000/103113300/103113299/b8691068_edited_2df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103120000/103113300/103113299/w717h480x0y0-00e1c4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio Awaits Your Next Stay!

[](https://www.expedia.co.uk/Boston-Hotels-Studio-Awaits-Your-Next-Stay.h103113299.Hotel-Information)

Bay Village

9.2/10

Wonderful

(5 reviews)

"Would stay again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

mark p.

£154

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Studio-Awaits-Your-Next-Stay.h103113299.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/98fb199d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/e1889f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/d112c10b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/e687838b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Come Visit Boston and Stay In Our Homey Studio

[](https://www.expedia.co.uk/Boston-Hotels-Come-Visit-Boston-And-Stay-In-Our-Homey-Studio.h89806135.Hotel-Information)

Downtown Boston

8.8/10

Excellent

(3 reviews)

"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dean and Courtenay M.

£169

includes taxes & fees

5 Feb - 6 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Come-Visit-Boston-And-Stay-In-Our-Homey-Studio.h89806135.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/dc25e9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/b1817ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/cf94f7fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/39520f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR3Bth Entire House/Steps to Downtown & TD Garden

[](https://www.expedia.co.uk/Boston-Hotels-3BR3Bth-Entire-HouseSteps-To-Downtown-TD-Garden.h119591835.Hotel-Information)

North End

10/10

Exceptional

(5 reviews)

"Clean and bright throughout, host was great with timely responses to all inquiries. Maybe not the best for young children bc of the all the stairs (which are beautiful btw)."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Margaret S.

£406

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-3BR3Bth-Entire-HouseSteps-To-Downtown-TD-Garden.h119591835.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/c6ab1483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/3634414f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/8e9f1637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/f822e23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Beacon Hills Studio next to State house

[](https://www.expedia.co.uk/Boston-Hotels-Gorgeous-Beacon-Hills-Studio-Next-To-State-House.h66847031.Hotel-Information)

Beacon Hill

9.8/10

Exceptional

(33 reviews)

"Loved the private outdoor patio"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robin P.

£260

includes taxes & fees

2 Feb - 3 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Gorgeous-Beacon-Hills-Studio-Next-To-State-House.h66847031.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/dd841a53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/1693fc21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/2c546fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/w1081h822x18y0-a5c5c4bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Back Bay Retreat, Steps from Prudential

[](https://www.expedia.co.uk/Boston-Hotels-Stylish-Back-Bay-Retreat.h112585043.Hotel-Information)

Back Bay

8.6/10

Excellent

(7 reviews)

"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

JEANPAUL

£218

includes taxes & fees

8 Feb - 9 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Stylish-Back-Bay-Retreat.h112585043.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/806f68c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/26112e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/c04cfe85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/957fbf4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright & Spacious Loft Steps to the Freedom Trail

[](https://www.expedia.co.uk/Boston-Hotels-Bright-Spacious-Loft-Steps-To-The-Freedom-Trail.h39536322.Hotel-Information)

Downtown Boston

10/10

Exceptional

(52 reviews)

"Trendy, clean room in great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rachel M.

£258

includes taxes & fees

23 Feb - 24 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Bright-Spacious-Loft-Steps-To-The-Freedom-Trail.h39536322.Hotel-Information)

![Interior entrance](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/41817f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room | Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/994122c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/ba4c8c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/37cdd40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 89 Marion

[](https://www.expedia.co.uk/Boston-Hotels-89-Marion.h89420220.Hotel-Information)

Coolidge Corner South Side

8.2/10

Very good

(271 reviews)

"Great location for getting off and on the train and clean. We were on the first floor and it was very loud. You would hear people up and down the stairs. And if you have people staying in the room above you, you can hear everything. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

samantha

[](https://www.expedia.co.uk/Boston-Hotels-89-Marion.h89420220.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/3bde57f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/31e3bef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/d74eb2f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/00ab78a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charlestown Houseboat Walk to attractions Be rocked to sleep

[](https://www.expedia.co.uk/Boston-Hotels-Charlestown-Houseboat-Walk-To-Attractions-Be-Rocked-To-Sleep.h37280691.Hotel-Information)

Thompson Square - Bunker Hill

9.6/10

Exceptional

(99 reviews)

"Great location, pet friendly, "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen W.

£283

includes taxes & fees

4 Feb - 5 Feb

[](https://www.expedia.co.uk/Boston-Hotels-Charlestown-Houseboat-Walk-To-Attractions-Be-Rocked-To-Sleep.h37280691.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-02-15&endDate=2026-02-16&regionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=APART_HOTEL)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=VACATION_HOME)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=CONDO)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=VILLA)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=COTTAGE)

Houseboats

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-02&d1=2026-05-02&endDate=2026-05-05&d2=2026-05-05&lodging=HOUSE_BOAT)

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## Top Winchester Hotel Reviews

![DoubleTree Suites by Hilton Hotel Boston - Cambridge](https://images.trvl-media.com/lodging/1000000/10000/1000/946/e477f850_y.jpg)

### DoubleTree Suites by Hilton Hotel Boston - Cambridge

10/10 Excellent

"The staff was exceptional. We had to extend our stay because our residential building suffered a fire and we still can’t return. From the very beginning, everyone was incredibly kind, attentive, and genuinely caring. They not only helped us extend our reservation, but also checked in on us and asked how we were doing, which meant a lot. We’re still staying here now and will likely extend again for the same reason. Everything has been spotless, both in the room and in the common areas. The indoor pool was wonderful and helped us disconnect for a bit during a stressful time. The food was also fantastic, especially the sirloin and the French fries. Thank you so much for the excellent service and for treating us with such empathy."

[](https://expedia.co.uk/Boston-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Boston-Cambridge.h946.Hotel-Information)

![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg)

### The Revolution Hotel

10/10 Excellent

"I chose this hotel last minute, we had an emergency in the family that needed us to stay in the Boston area. Reserving was easy, and the price totally reasonable, ESPECIALLY due to the last minute nature of the reservation. Beautiful hotel, with a lovely coffee shop in the lobby! The room was spacious, clean, and fully stocked-we got a kitchenette! Every employee we dealt with was helpful, polite, and fantastic to talk to!"

[](https://expedia.co.uk/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information)

![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg)

### Hilton Boston Logan Airport

10/10 Excellent

"Clean room, quiet, convenient."

[](https://expedia.co.uk/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information)

![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg)

### Encore Boston Harbor

10/10 Excellent

"GREAT LOCATION"

[](https://expedia.co.uk/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information)

![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg)

### The Dagny Boston

10/10 Excellent

"Very clean, friendly staff, awesome gym. "

[](https://expedia.co.uk/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information)

![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg)

### Seaport Hotel Boston

10/10 Excellent

"Wonderful staff and great experience! "

[](https://expedia.co.uk/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information)

![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg)

### Hyatt Regency Boston

10/10 Excellent

"Great staff. Great location"

[](https://expedia.co.uk/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information)

![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg)

### The Godfrey Hotel Boston

10/10 Excellent

"Have been very interested in staying at the Godfrey. Staff were great and very accommodating. I wished the hitel had a better libby though as I though the coffee shop and restaurant were openly attached to the lobby which they were not. All in all a great place to stay and walking distance to the subway and amenities. Gym needs cleaning soray and heavier plates for squat bar please!"

[](https://expedia.co.uk/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information)

![Hyatt Place Boston/Seaport District](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/5fe1e844_y.jpg)

### Hyatt Place Boston/Seaport District

10/10 Excellent

"No complaints. Everything was perfect. "

[](https://expedia.co.uk/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information)

## Find out more about Winchester

**Everything you need to know about** **Winchester** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Winchester holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winchester holiday rentals we have selected for you start as low as £95 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Winchester rentals**

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

- Trending destinations on Expedia.co.uk
- All accommodation types in Winchester

### Trending destinations on Expedia.co.uk

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- [Northumberland Holiday Rentals ](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations)
- [Herefordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations)
- [Essex Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations)
- [Cumbria Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations)
- [Yorkshire Holiday Rentals ](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals)
- [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
- [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals)
- [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

- [Houseboats in Winchester ](https://expedia.co.uk/Winchester-Houseboats.d175481-aaHouseboats.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find holiday rentals in Winchester?

### What are some of the best holiday rentals that Winchester has to offer?

### What can I see and do in Winchester?

### What are holiday rentals like in Winchester?

### Expedia's Latest Trends

Hotels

- [Cambridge Cheap Hotels](https://expedia.co.uk/Cambridge-Hotels-Budget-Hotels.0-0-d8093-tBudgetHotels.Travel-Guide-Filter-Hotels)
- [Cambridge Gay-Friendly Hotels](https://expedia.co.uk/Cambridge-Hotels-Gay-Friendly-Hotel.0-0-d8093-tGayFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Four Seasons Hotels in Cambridge](https://expedia.co.uk/Cambridge-Hotels-Four-Seasons.0-0-d8093--bFourSeasons.Travel-Guide-Filter-Hotels)
- [Salem Accommodation](https://expedia.co.uk/Salem-Hotels.d6600.Travel-Guide-Hotels)
- [Burlington Accommodation](https://expedia.co.uk/Burlington-Hotels.d6306.Travel-Guide-Hotels)
- [Brookline Accommodation](https://expedia.co.uk/Brookline-Hotels.d7091.Travel-Guide-Hotels)
- [Salem Cheap Hotels](https://expedia.co.uk/Salem-Hotels-Budget-Hotels.0-0-d6600-tBudgetHotels.Travel-Guide-Filter-Hotels)
- [Marriott Hotels & Resorts Hotels in Hull](https://expedia.co.uk/Hull-Hotels-Marriott-Hotels-Resorts.0-0-d117382--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
- [Cambridge Spa Hotels](https://expedia.co.uk/Cambridge-Hotels-Spa-Hotels.0-0-d8093-tSpaHotels.Travel-Guide-Filter-Hotels)
- [Hilton Hotels Hotels in Weymouth](https://expedia.co.uk/Weymouth-Hotels-Hilton-Hotels.0-0-d173854--bHiltonHotels.Travel-Guide-Filter-Hotels)
- [Lexington Accommodation](https://expedia.co.uk/Lexington-Hotels.d8601.Travel-Guide-Hotels)
- [Cambridge Accommodation](https://expedia.co.uk/Cambridge-Hotels.d8093.Travel-Guide-Hotels)
- [Weymouth Accommodation](https://expedia.co.uk/Weymouth-Hotels.d173854.Travel-Guide-Hotels)
- [Wellesley Accommodation](https://expedia.co.uk/Wellesley-Hotels.d7665.Travel-Guide-Hotels)
- [Marriott Hotels & Resorts Hotels in Weymouth](https://expedia.co.uk/Weymouth-Hotels-Marriott-Hotels-Resorts.0-0-d173854--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
- [Woburn Spa Hotels](https://expedia.co.uk/Woburn-Hotels-Spa-Hotels.0-0-d10373-tSpaHotels.Travel-Guide-Filter-Hotels)

Flights

- [Flights to BOS](https://expedia.co.uk/Cheap-Flights-To-Salem.d6600.Travel-Guide-Flights)
- [Flights to BOS](https://expedia.co.uk/Cheap-Flights-To-Cambridge.d8093.Travel-Guide-Flights)

Cars

- [van Car Hire in Hull](https://expedia.co.uk/Van-Car-Rentals-In-Hull.d117382-tVan.Car-Rental-Guide-Class)
- [Car rental in Dedham](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Dedham.d6738.Car-Hire-Guide)
- [Car rental in Cambridge](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Cambridge.d8093.Car-Hire-Guide)

Activities

- [Things to do in Woburn](https://expedia.co.uk/Things-To-Do-In-Woburn.d10373.Travel-Guide-Activities)
- [Things to do in Salem](https://expedia.co.uk/Things-To-Do-In-Salem.d6600.Travel-Guide-Activities)
- [Things to do in Braintree](https://expedia.co.uk/Things-To-Do-In-Braintree.d6806.Travel-Guide-Activities)
- [Things to do in Concord](https://expedia.co.uk/Things-To-Do-In-Concord.d6532.Travel-Guide-Activities)

Packages

- [Salem City Breaks](https://expedia.co.uk/Salem.d6600.Holidays-City-Breaks)
- [Cambridge City Breaks](https://expedia.co.uk/Cambridge.d8093.Holidays-City-Breaks)

General

- [Visit Cambridge](https://expedia.co.uk/Cambridge.dx8093)
- [Visit Concord](https://expedia.co.uk/Concord.dx6532)
- [Visit Salem](https://expedia.co.uk/Salem.dx6600)

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