Title: Holiday Rentals Chester from £236: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Hotels in Chester](https://expedia.co.uk/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d3000440455.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d3000440455.Holidays-City-Breaks)

![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Patricia Knorr

![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Save instantly and earn perks with One Key  
[Learn about One Key](https://www.expedia.co.uk/welcome-one-key)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&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)

In three months

[19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[17 Jul - 19 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester holiday rentals

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/w1322h734x2y1-d973a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### First Floor Studio Apartment in Historic Chestertown

[](https://www.expedia.co.uk/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

Chestertown

9.6/10

Exceptional

(108 reviews)

"Every thing was great"

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

lesia k.

£123

includes taxes & fees

31 Mar - 1 Apr

[](https://www.expedia.co.uk/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b4e88275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/ee75c514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b0be7e2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/daf32ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information)

Rock Hall

10/10

Exceptional

(18 reviews)

"Close to Main Street. Very nice and spacious accommodations."

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

Michael D.

£215

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table football](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. 

[](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

Grasonville

9.6/10

Exceptional

(12 reviews)

"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "

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

Joe C.

£315

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/w1024h678x0y5-f3e384c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Coastal/Country Home w/3 Acres & Sauna!

[](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

Stevensville

9.6/10

Exceptional

(35 reviews)

"Great stay, would do it again."

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

Brandon D.

£236

includes taxes & fees

12 Apr - 13 Apr

[](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/57f188cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax on Kent Island in a 4 Bedroom Home w/Waterview!

[](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

Stevensville

9.8/10

Exceptional

(43 reviews)

"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"

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

Supriya V.

£231

includes taxes & fees

12 Apr - 13 Apr

[](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/21befbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/8ae0a25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/ce9b7709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bayside Cottage steps from Rock Hall Harbor

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

Rock Hall

10/10

Exceptional

(2 reviews)

"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"

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

Dorothy R.

£270

includes taxes & fees

20 Apr - 21 Apr

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/86c425c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a5c24734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 2 bedroom house with private parking in a nice neighborhood

[](https://www.expedia.co.uk/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

Arnold

9.4/10

Exceptional

(37 reviews)

"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "

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

Traci L.

£247

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/128000000/127220000/127211600/127211540/db0301b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/128000000/127220000/127211600/127211540/85fe87ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/128000000/127220000/127211600/127211540/8bd83756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/128000000/127220000/127211600/127211540/1c7b4ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pool + Hot Tub + Pickleball | Waterfront

[](https://www.expedia.co.uk/Church-Hill-Hotels-Stillwater-At-Kennersley.h127211540.Hotel-Information)

Church Hill

£692

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Church-Hill-Hotels-Stillwater-At-Kennersley.h127211540.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cad4612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cab7732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/3334515c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/f2ba56b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bay Ridge unit by Downtown Annapolis and Quiet Waters Park 

[](https://www.expedia.co.uk/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information)

Annapolis

8.8/10

Excellent

(3 reviews)

"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."

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

William

£361

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/8d73bbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/491acaae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/45c5363e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/28c9186e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pool Loft Suite | Bay Access & Beach Passes

[](https://www.expedia.co.uk/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information)

Cape Saint Claire

10/10

Exceptional

(4 reviews)

"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."

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

Ana S.

£290

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/b2a36b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/95f44d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8c6112e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Oasis of Annapolis Star

[](https://www.expedia.co.uk/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

Annapolis

10/10

Exceptional

(81 reviews)

"Owners were great hosts. Loved this property!"

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

Thomas

£307

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/3f3bd4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/457a4a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/42bbbfcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/bf60932b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Beach! King Bed & Free Beach Passes

[](https://www.expedia.co.uk/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

North Beach

10/10

Exceptional

(19 reviews)

"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"

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

Elaine D.

£275

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/7e2b4765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/c9b926ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2br home w/ parking in downtown Annapolis

[](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

Historic District

10/10

Exceptional

(75 reviews)

"Welcoming host, great location and easy parking "

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

Chris B.

£243

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/60e252be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/9b7348ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/54c5a0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/e06d3ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Unit | Dock, Kayaks & SUPs Included

[](https://www.expedia.co.uk/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information)

Edgewater

10/10

Exceptional

(3 reviews)

"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"

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

Daniel K.

£240

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information)

![Oven, stovetop](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/009658d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/1e2f03eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f5323c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f21ef3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 40' Bristol sailboat with spectacular views

[](https://www.expedia.co.uk/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information)

Stevensville

£325

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/4b955546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/9c7dbc30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/10010e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/d131334a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

[](https://www.expedia.co.uk/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

Arnold

9.8/10

Exceptional

(8 reviews)

"Great place!"

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

Chris A.

£269

includes taxes & fees

1 Apr - 2 Apr

[](https://www.expedia.co.uk/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/c81ba3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/0348d35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/85376bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/733d81ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Pet-Friendly Stay - Near Bay & Beaches.

[](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information)

Annapolis

10/10

Exceptional

(7 reviews)

"Very clean and very convenient location for our trip. "

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

Greg S.

£392

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-5f725067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h508x0y136-4ba3382c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-97b0328a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w642h780x229y0-93850baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hideaway Spot- Waterfront w/ Dock on Long Cove

[](https://www.expedia.co.uk/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.Hotel-Information)

Glen Burnie

8.8/10

Excellent

(10 reviews)

"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."

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

Jeffrey S.

£273

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/d00ee2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/8156a7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/9df6bc62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/48c7542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Retreat - 7 mins from downtown Annapolis!

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information)

Hillsmere

10/10

Exceptional

(6 reviews)

"Great house in cute neighborhood. Thanks for a very comfortable stay!"

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

Paul C.

£401

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/b1ed4047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/852031b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/cc9a4892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/139d479a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

[](https://www.expedia.co.uk/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.Hotel-Information)

Pasadena

£337

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.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=2026-04-12&endDate=2026-04-13&regionId=3000440455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Houseboats

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=HOUSE_BOAT)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=APARTMENT)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=COTTAGE)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=CONDO)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=VILLA)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Holiday-Rentals.d3000440455.Travel-Guide-HolidayRentals)[

Sign up, it's free

](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Holiday-Rentals.d3000440455.Travel-Guide-HolidayRentals)

## Top Chester Hotel Reviews

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"Location great . Hotel impressive for the cost. "

[](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802_y.jpg)

### Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good

"I had a great stay & everything was great"

[](https://expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![SpringHill Suites by Marriott Annapolis](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg)

### SpringHill Suites by Marriott Annapolis

6/10 Okay

"Overall good. However, when I search Expdia it was for free parking. This hotel cam up on the search. This hotel charged for parking. That was unexpected."

[](https://expedia.co.uk/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information)

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Nice breakfast selection, food was fresh and delish."

[](https://expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf_y.jpg)

### The Westin Annapolis

10/10 Excellent

"Love This hotel and the walking distance to everything "

[](https://expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information)

![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"No breakfast, I sleep in."

[](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/ff58e28e_y.jpg)

### Hampton Inn & Suites Annapolis

4/10 Poor

"The hotel charged a $10.60 parking fee but provided no service in consideration of this fee. I was not asked about the description of my vehicle or given a parking pass to place in the vehicle, presumably as a way to identify that I had paid. If the intent of this parking-fee is policy is to dissuade non-guests from parking on the hotel premises, nothing in this policy would achieve this goal. A car, whose driver paid the fee as a guest, would appear the same as the car of a non-guest who did not pay the fee. This policy appears capricious at best, and a shake-down at worst. I will be demanding a refund of the $10.60 that I paid."

[](https://expedia.co.uk/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information)

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Julie is amazing!"

[](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information)

![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd_y.jpg)

### Inn at Perry Cabin

10/10 Excellent

"everything was perfect!"

[](https://expedia.co.uk/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information)

## Find out more about Chester

**Everything you need to know about** **Chester** **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 Chester 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 Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

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

Whenever you want to travel, a warm welcome awaits you in Chester. 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 Chester 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 Chester holiday rentals we have selected for you start as low as £236 per night. Entering your travel dates in the search wizard you might find even better deals!

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

At Expedia, we put the best Chester 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 Chester 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 Chester 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 Chester. 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 Chester

### Trending destinations on Expedia.co.uk

- [Holiday Rentals in the Cotswold ](https://www.expedia.co.uk/lp/b/vr/cotswold)
- [Holiday Rentals in Lake District ](https://www.expedia.co.uk/lp/b/vr/lake-district)
- [Devon Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations)
- [Norfolk Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations)
- [Bedfordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations)
- [Dorset Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations)
- [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)

- [Villas in Chester ](https://expedia.co.uk/Chester-Villas.d3000440455-aaVillas.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find holiday rentals in Chester?

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

### How many holiday rentals will I find in Chester?

### What’s there to see and do in Chester?

### What’s a holiday rental in Chester like?