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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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winchester holiday rentals

Rooftop terrace

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, (664 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is ₹38,474
₹44,225 total
includes taxes & fees
11 Sept - 12 Sept
Marriott Vacation Club® at Custom House, Boston
Lobby lounge

2. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (739 reviews)
"Great for the price; central to everything"
United States
afshin
The price is ₹19,890
₹34,322 total
includes taxes & fees
10 Sept - 11 Sept
Global Luxury Suites Downtown Boston
Lobby

3. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (314 reviews)
"Everything is good"
United States
Kilyen
The price is ₹14,883
₹26,884 total
includes taxes & fees
13 Sept - 14 Sept
Kasa Boston at Fenway
Studio | Iron/ironing board, free WiFi

4. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (20 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 ₹15,502
₹29,768 total
includes taxes & fees
8 Sept - 9 Sept
The Concord Hotel
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

5. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (232 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is ₹18,049
₹37,041 total
includes taxes & fees
10 Sept - 11 Sept
Charlesgate Suites
Front of property

6. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (417 reviews)
"Great property beautiful vintage building great location"
United States
James
The price is ₹18,805
₹30,849 total
includes taxes & fees
10 Sept - 11 Sept
Maverick Suites at 28 Fenway
42-inch TV with satellite channels

7. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (171 reviews)
"Well located"
United States
Evelyn
The price is ₹15,308
₹26,287 total
includes taxes & fees
8 Sept - 9 Sept
Maverick Suites at 400 Columbus Ave
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

8. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (337 reviews)
"Location is great"
United States
Eria
The price is ₹9,780
₹16,130 total
includes taxes & fees
8 Sept - 9 Sept
Premier Suites - Bay Village
Premium Apartment | Living area | 24-inch Smart TV with digital channels

9. 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 ₹15,119
₹29,328 total
includes taxes & fees
8 Sept - 9 Sept
The Chester Hotel
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

10. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (462 reviews)
"The Property was comfortable, close to public transport, The Goston Common and lots of lively eateries."
United Kingdom
Lisa
The price is ₹11,396
₹19,074 total
includes taxes & fees
8 Sept - 9 Sept
Temple Place Suites
Front of property

11. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (145 reviews)
"Worth the stay"
Canada
Akansha
The price is ₹12,821
₹23,427 total
includes taxes & fees
8 Sept - 9 Sept
Maverick Suites at 40 Temple St
Exterior

12. 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, (202 reviews)
"Great location, really cool place!"
United States
lane
The price is ₹14,603
₹25,476 total
includes taxes & fees
8 Sept - 9 Sept
Maverick Suites at 245 Newbury St
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services

13. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (40 reviews)
"This place is absolutely stunning I would definitely book again. "
United States
Klaudia
The price is ₹56,867
₹81,662 total
includes taxes & fees
9 Sept - 10 Sept
The Monty Boston
Terrace/patio

14. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,265 reviews)
"Friendly staff. Bed was very comfortable and the kitchen was a plus!"
United States
Evelyn
The price is ₹14,919
₹16,664 total
includes taxes & fees
17 Sept - 18 Sept
Crescent Suites Hotel
Interior entrance

15. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (310 reviews)
"Stayed in the economy suite, very suitable for a couple! Very clean room and I have never had an easier check-in process!!"
United States
Paula
The price is ₹11,673
₹21,482 total
includes taxes & fees
8 Sept - 9 Sept
Maverick Suites at 89 Marion
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

16. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (21 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 ₹23,991
₹37,897 total
includes taxes & fees
13 Sept - 14 Sept
Symple Live
30-inch flat-screen TV with satellite channels, TV

17. Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very good, (85 reviews)
"It was very close to stores to go shopping and amazing spot to get last minute reservations for dinner"
United States
Talyciah
The price is ₹13,395
₹24,087 total
includes taxes & fees
9 Sept - 10 Sept
Maverick Suites at 402 Columbus Ave
Indoor pool, pool umbrellas, pool loungers

18. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (207 reviews)
"Good place and nice location but bed sheets and pillows were stained and had hair on them which is unacceptable."
United Kingdom
Leigh
The price is ₹22,273
₹36,466 total
includes taxes & fees
13 Sept - 14 Sept
Global Luxury Suites East Boston
Apartment (1 Bedroom) | Interior

19. Apt in Historic Lynn Neighborhood: 5 Mi to Salem!

Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
3.0 star property
Lynn
The price is ₹17,104
₹38,418 total
includes taxes & fees
12 Sept - 13 Sept
Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
House (SeaCity View) | Exterior

20. Seacity View

Seacity View
2.0 star property
Swampscott
7.0 out of 10, Good, (2 reviews)
"Beautiful house!"
United States
carla n
The price is ₹29,957
₹60,115 total
includes taxes & fees
14 Sept - 15 Sept
Seacity View
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

The Royal Sonesta Boston

The Royal Sonesta Boston

10/10 Excellent
"Great location, kids LOVED the pool and staff was extremely helpful"
Richard 1-night trip
Posted less than an hour ago
The Royal Sonesta Boston

Find out more about Winchester

Holiday Rentals in Winchester

Search for holiday rentals in Winchester on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Griffin Photography Museum, 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.

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. TD Garden and Fenway Park 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.