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

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winchester holiday rentals

Living area

1. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (36 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is S$373
includes taxes & fees
11 Aug - 12 Aug
The Chester Hotel
Front of property

2. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.8 out of 10, Good, (141 reviews)
"Worth the stay"
Canada
Akansha
The price is S$324
includes taxes & fees
10 Aug - 11 Aug
Maverick Suites at 40 Temple St
Desk, iron/ironing board, free WiFi, bed sheets

3. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (433 reviews)
"Great location so close to everything"
United States
Hunter
The price is S$225
includes taxes & fees
10 Aug - 11 Aug
Temple Place Suites
Exterior

4. 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, (197 reviews)
"Location was perfect! The room was great and exactly what I needed for my business trip"
United States
Michael
The price is S$337
includes taxes & fees
10 Aug - 11 Aug
Maverick Suites at 245 Newbury St
Iron/ironing board, free WiFi

5. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.0 out of 10, Good, (10 reviews)
"Clean room and linens, great location and comfortable bed. Only complaint is the street noise and sounds from residents in upstairs apartment which was kind of loud. All things considered I’d stay again as it was a good value spot"
United States
Nancy
The price is S$367
includes taxes & fees
11 Aug - 12 Aug
The Concord Hotel
Terrace/patio

6. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,243 reviews)
"Dana is a great host, nice spacious rooms"
United States
joseph
The price is S$224
includes taxes & fees
16 Aug - 17 Aug
Crescent Suites Hotel
Front of property

7. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (402 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
The price is S$354
includes taxes & fees
10 Aug - 11 Aug
Maverick Suites at 28 Fenway
Iron/ironing board, free WiFi, bed sheets

8. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (320 reviews)
"Lovely small property with thoughtful touches like cool water bottles & Nespresso available 24hrs. I had to take a last minute Zoom call and the front desk reserved the business center room for me. The rooms themselves are a bit small but very comfortable beds and linens."
United States
Theresa
The price is S$210
includes taxes & fees
10 Aug - 11 Aug
Premier Suites - Bay Village
Premium bedding, desk, iron/ironing board, free WiFi

9. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (224 reviews)
"Very nice room and close to fenway"
United States
timothy
The price is S$450
includes taxes & fees
10 Aug - 11 Aug
Charlesgate Suites
42-inch TV with satellite channels

10. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (161 reviews)
"Well located"
United States
Evelyn
The price is S$305
includes taxes & fees
10 Aug - 11 Aug
Maverick Suites at 400 Columbus Ave
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 Dagny Boston

The Dagny Boston

10/10 Excellent
"I was in Boston for a wedding and the location worked. I arrived early and was able to check in at 11am, which was fantastic. Lobby is classic, rooms modern and comfortable. Staff were all extremely helpful."
Rebecca 2-night trip
Posted 1 hour ago
The Dagny Boston

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.