A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Our top choices for Winchester holiday rentals

1. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (667 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is £543
includes taxes & fees
8 Oct - 9 Oct
Marriott Vacation Club® at Custom House, Boston

2. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,277 reviews)
"Great location, close to restaurants and stores. Beautiful rooms. Close enought to Boston without all the traffic. Close to Mass Pike."
United States
Mark
The price is £129
includes taxes & fees
18 Oct - 19 Oct
Crescent Suites Hotel

3. Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place to stay in Medford. Everything was great and we ended up only had two persons staying here, for which it was great!"
United States
Michael C.
The price is £199
includes taxes & fees
28 Sept - 29 Sept
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

4. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (319 reviews)
"Excellent property upscale amenities full kitchen perfect in every way and my room was only a studio I’ll definitely be back next time to try a larger room just to see what they’re like"
United States
Dirk
Kasa Boston at Fenway

5. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (148 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is £248
includes taxes & fees
4 Oct - 5 Oct
Maverick Suites at 40 Temple St

6. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (203 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is £252
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 245 Newbury St

7. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (425 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is £211
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 28 Fenway

8. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (24 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is £322
includes taxes & fees
30 Sept - 1 Oct
The Concord Hotel

9. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (172 reviews)
"Well located"
United States
Evelyn
The price is £194
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 400 Columbus Ave

10. 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
Melrose
10.0 out of 10, Exceptional, (152 reviews)
"We enjoyed our stay! The house is beautiful, clean and as described. Greg was extremely helpful and very quick to respond. Neighborhood felt safe and would definitely stay again!"
United States
KATIE G.
The price is £381
includes taxes & fees
22 Sept - 23 Sept
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

11. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (745 reviews)
"Friendly sat at Front and the property is very nice it was useful for a quick work trip. Easy to get around well lit and maintained"
United States
Christopher
The price is £366
includes taxes & fees
30 Sept - 1 Oct
Global Luxury Suites Downtown Boston

12. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (478 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is £151
includes taxes & fees
28 Sept - 29 Sept
Temple Place Suites

13. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (237 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is £344
includes taxes & fees
30 Sept - 1 Oct
Charlesgate Suites

14. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (345 reviews)
"Location is great"
United States
Eria
The price is £151
includes taxes & fees
30 Sept - 1 Oct
Premier Suites - Bay Village

15. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (327 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is £237
includes taxes & fees
29 Sept - 30 Sept
Near Boston Historic two-bedroom with Modern Amenities

16. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (314 reviews)
"Room was clean, neat area."
United States
Keir
The price is £164
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 89 Marion

17. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (22 reviews)
"Great location, close to the T line, grocery store nearby. Clean, quiet and very comfortable accommodations, especially the best bed I’ve slept in at a rental location. Had everything we needed, looking forward to coming back!"
United States
Lori
The price is £413
includes taxes & fees
30 Sept - 1 Oct
Symple Live

18. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is £260
includes taxes & fees
30 Sept - 1 Oct
The Chester Hotel

19. Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Ward Two
10.0 out of 10, Exceptional, (24 reviews)
"Clean, comfortable and convenient! Communication was detailed, with prompt replies. Everything you need is within 1/2 mile. We enjoyed our stay and will definitely be staying here again. Thanks!!"
United States
Jan L.
The price is £380
includes taxes & fees
24 Sept - 25 Sept
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

20. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (41 reviews)
"This place is absolutely stunning I would definitely book again. "
United States
Klaudia
The price is £768
includes taxes & fees
4 Oct - 5 Oct
The Monty Boston
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.
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Top Winchester Hotel Reviews

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, cottages, apart-hotels, cabins, 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 £129 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

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Winter Pond, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its football matches and lake views.

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

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday home rental outside of Winchester offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

How many holiday rentals are there in Winchester?

Choose from 3 Expedia holiday rentals in Winchester for a memorable holiday.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Winter Pond, or get outside and enjoy nature at Boston Common. Fenway Park and Encore Boston Harbor are other popular places to visit in the area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.