Winchester Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winchester holiday rentals

An outdoor patio with round tables and chairs, surrounded by green umbrellas.

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,348 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
The price is S$217
includes taxes & fees
13 Nov - 14 Nov
Crescent Suites Hotel
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

2. 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, (681 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 S$337
includes taxes & fees
25 Nov - 26 Nov
Marriott Vacation Club® at Custom House, Boston
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

3. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is S$297
includes taxes & fees
7 Dec - 8 Dec
Global Luxury Suites Downtown Boston
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

4. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (348 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is S$379
includes taxes & fees
8 Dec - 9 Dec
Kasa Boston at Fenway
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

5. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (43 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
The price is S$374
includes taxes & fees
8 Nov - 9 Nov
The Chester Hotel
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

6. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (474 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is S$276
includes taxes & fees
8 Dec - 9 Dec
Maverick Suites at 28 Fenway
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, (355 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is S$261
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 89 Marion
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

8. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (215 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is S$325
includes taxes & fees
6 Dec - 7 Dec
Global Luxury Suites East Boston
A row of brick buildings with storefronts, including a bakery and a liquor store.

9. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (219 reviews)
"Great location - plenty to do."
United States
Chloe
The price is S$285
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 245 Newbury St
A modern hotel room with a bed, a desk, a sofa, and a dining area.

10. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (246 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is S$484
includes taxes & fees
9 Nov - 10 Nov
Charlesgate Suites
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

11. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (39 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is S$398
includes taxes & fees
11 Nov - 12 Nov
The Concord Hotel
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

12. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (165 reviews)
"Great property in a great location. Tons of food options nearby. Walking distance to Target and Whole Foods. Easy access to the Blue line. The neighborhood was quiet and clean. Boston common is just a block away. Definitely would stay again and highly recommend."
United States
TommyWallace
The price is S$284
includes taxes & fees
8 Dec - 9 Dec
Maverick Suites at 40 Temple St
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

A modern living room with a fireplace, seating area, and large windows.
Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
Watertown

10/10 Excellent

Room is clean and spacious. Bed mattress and sofa bed are comfortable and they promote good sleep. Location is excellent with good shopping and eateries in vicinity. Enjoyed our stay
Singapore
SAW KIM
Reviewed June 15, 2025
Hampton Inn & Suites Watertown Boston

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.