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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Top Holiday Rentals in Winchester

Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites

Bay Village Suites

2.0 star property
Bay Village
6.4 out of 10, (248)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Lobby lounge
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4.0 star property
Chinatown
8.0 out of 10, Very good, (626)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
The price is 3.000.339 ₫
4.630.845 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Global Luxury Suites Downtown Boston
Exterior
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, (151)
"Good location, clean and quiet. Only thing that could be improved on would be luggage storage before check in "
United States
Kristee
Maverick Suites at 245 Newbury St
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village

Premier Suites - Bay Village

2.0 star property
Bay Village
6.4 out of 10, (251)
"Clean room, good location, check in check out easily!"
United States
HIEN T
Premier Suites - Bay Village
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites

Temple Place Suites

2.5 star property
Downtown Boston
7.0 out of 10, Good, (321)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is 2.270.026 ₫
4.276.255 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Temple Place Suites
Front of property
Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2.0 star property
Beacon Hill
7.6 out of 10, Good, (102)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
Maverick Suites at 40 Temple St
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2.0 star property
South End
7.2 out of 10, Good, (131)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
Maverick Suites at 400 Columbus Ave
Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (321)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
The price is 2.538.949 ₫
5.494.580 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Maverick Suites at 28 Fenway
Interior entrance
Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

2.0 star property
Coolidge Corner South Side
8.4 out of 10, Very good, (269)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
Maverick Suites at 89 Marion
Property grounds
Crescent Suites Hotel

Crescent Suites Hotel

3.0 star property
South Side
9.6 out of 10, Exceptional, (1139)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services
The Monty Boston

The Monty Boston

2.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (28)
"Amazing property, would stay again."
United States
Doug
The price is 11.600.600 ₫
17.881.007 ₫ total
includes taxes & fees
6 Dec - 7 Dec
The Monty Boston
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Charlesgate Suites

3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is 6.116.680 ₫
11.577.135 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Charlesgate Suites
City Studio | Egyptian cotton sheets, premium bedding, memory-foam beds
The Chester Hotel

The Chester Hotel

4.0 star property
South End
8.6 out of 10, Excellent, (27)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is 6.264.324 ₫
11.898.359 ₫ total
includes taxes & fees
30 Nov - 1 Dec
The Chester Hotel
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels
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, (67)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 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 Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Outstanding staff and overall experience. Very nice hotel. "
Kevin 1-night trip
Posted 7 hours ago
The Godfrey Hotel 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.

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 Harvard Square 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.