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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winchester holiday rentals

A bedroom with a bed, desk, chair, dresser, and two bedside lamps.

1. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
3.0 star property
Winchester
10.0 out of 10, Exceptional, (1 review)
"Clean and spacious private entrance mother-in-law suite in a nice and quiet neighborhood. About a 25-40 minute ride, depending on traffic, into Boston."
United States
Selena
The price is ₹11,242
₹25,465 total
includes taxes & fees
17 Nov - 18 Nov
Train to Boston! Cozy Apartment in Winchester
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

2. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,329 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is ₹12,213
₹13,642 total
includes taxes & fees
22 Nov - 23 Nov
Crescent Suites Hotel
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

3. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (678 reviews)
"I can’t believe this property is a hotel and not a historic landmark. If you like historical places this is the place to stay in Boston."
United States
Benny
The price is ₹27,485
₹31,594 total
includes taxes & fees
23 Nov - 24 Nov
Marriott Vacation Club® at Custom House, Boston
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

4. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (41 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
The price is ₹10,883
₹24,455 total
includes taxes & fees
9 Nov - 10 Nov
The Chester Hotel
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

5. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (335 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
The price is ₹16,130
₹27,076 total
includes taxes & fees
29 Oct - 30 Oct
Kasa Boston at Fenway
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

6. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (767 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is ₹10,475
₹23,214 total
includes taxes & fees
22 Nov - 23 Nov
Global Luxury Suites Downtown Boston
A wooden hallway with a patterned floor leading to a door.

7. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (346 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is ₹8,647
₹18,100 total
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 89 Marion
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

8. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (456 reviews)
"Really pretty well maintained accomodation close to a lot of cool things to do in boston. its also pretty close to the train and bus station which was helpful to get around"
United States
Rakshitha
The price is ₹10,798
₹21,642 total
includes taxes & fees
8 Nov - 9 Nov
Maverick Suites at 28 Fenway
A modern hotel room with a bed, a desk, a sofa, and a dining area.

9. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (243 reviews)
"Spacers, convenient location"
United States
Svetlana
The price is ₹16,310
₹35,099 total
includes taxes & fees
22 Nov - 23 Nov
Charlesgate Suites
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

10. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (36 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is ₹15,263
₹29,490 total
includes taxes & fees
22 Nov - 23 Nov
The Concord Hotel
A row of brick buildings with storefronts, including a bakery and a liquor store.

11. 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, (209 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is ₹12,243
₹22,761 total
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 245 Newbury St
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

12. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (527 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
The price is ₹8,495
₹15,737 total
includes taxes & fees
22 Nov - 23 Nov
Temple Place Suites
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

Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

8/10 Good
"Great location. Bad mattress"
Nicola J 1-night trip
Posted 5 hours ago
Wyndham Boston Beacon Hill

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 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.

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.