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Check prices for these dates

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Top Holiday Rentals in Winchester

Lobby lounge
Global Luxury Suites Downtown Boston
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (615)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
Global Luxury Suites Downtown Boston
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave
Maverick Suites at 400 Columbus Ave
2.0 star property
7.2 out of 10, Good, (126)
"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
The price is ฿3,002
฿6,459 total
includes taxes & fees
18 Nov - 19 Nov
Maverick Suites at 400 Columbus Ave
Individually furnished, laptop workspace, iron/ironing board, bed sheets
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
4.0 star property
9.2 out of 10, Wonderful, (944)
"The property was awesome, well located, not far to jump on trains etc Close to MGM musical hall, which was the reason for our trip. Would 100% recommend this property if your looking for a nice peaceful area but close enough to all the popular touristy areas. Loved our stay, thank you "
United Kingdom
Lyndsey
The price is ฿5,563
฿6,562 total
includes taxes & fees
9 Nov - 10 Nov
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
Deluxe Studio Suite (2nd Floor - Unit 202) | 1 bedroom, individually furnished, iron/ironing board, free WiFi
Maverick Suites at 28 Fenway
Maverick Suites at 28 Fenway
3.0 star property
8.8 out of 10, Excellent, (303)
"great location"
United States
Mario
The price is ฿3,169
฿6,839 total
includes taxes & fees
18 Nov - 19 Nov
Maverick Suites at 28 Fenway
Front of property
Maverick Suites at 40 Temple St
Maverick Suites at 40 Temple St
2.0 star property
7.4 out of 10, Good, (100)
"Great location "
Canada
James
The price is ฿4,337
฿7,993 total
includes taxes & fees
19 Nov - 20 Nov
Maverick Suites at 40 Temple St
Exterior
Maverick Suites at 245 Newbury St
Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (150)
"Clean. Bed super comfortable, easy walk to Fenway, restaurants, subway, shops, library"
United States
Elizabeth rising
The price is ฿4,615
฿8,312 total
includes taxes & fees
18 Nov - 19 Nov
Maverick Suites at 245 Newbury St
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites
Bay Village Suites
2.0 star property
6.4 out of 10, (235)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Apartment | 1 bedroom, premium bedding, desk, iron/ironing board
Charlesgate Suites
Charlesgate Suites
3.5 star property
9.4 out of 10, Exceptional, (194)
"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 ฿6,836
฿13,497 total
includes taxes & fees
10 Nov - 11 Nov
Charlesgate Suites
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village
Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (237)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is ฿6,497
฿9,166 total
includes taxes & fees
26 Oct - 27 Oct
Premier Suites - Bay Village
Deluxe Studio | 1 bedroom, desk, iron/ironing board, free WiFi
Temple Place Suites
Temple Place Suites
2.5 star property
7.0 out of 10, Good, (298)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is ฿3,120
฿5,654 total
includes taxes & fees
16 Nov - 17 Nov
Temple Place Suites
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
8.0 out of 10, Very good, (65)
"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
The price is ฿3,002
฿6,459 total
includes taxes & fees
25 Nov - 26 Nov
Maverick Suites at 402 Columbus Ave
Property amenity
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
4.0 star property
8.8 out of 10, Excellent, (273)
"Easy check in and clean property with in unit laundry"
United States
Sarah
The price is ฿6,152
฿7,256 total
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Interior entrance
Maverick Suites at 89 Marion
Maverick Suites at 89 Marion
2.0 star property
8.4 out of 10, Very good, (261)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
The price is ฿3,670
฿7,022 total
includes taxes & fees
23 Nov - 24 Nov
Maverick Suites at 89 Marion
Property grounds
Crescent Suites Hotel
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (1114)
"The staff were friendly and the accommodation was good"
United States
Sudha
Crescent Suites Hotel
City Studio | 1 bedroom, Egyptian cotton sheets, premium bedding, memory-foam beds
The Chester Hotel
The Chester Hotel
4.0 star property
8.4 out of 10, Very good, (25)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is ฿5,828
฿12,527 total
includes taxes & fees
26 Oct - 27 Oct
The Chester Hotel
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
"Excellent hotel!"
Scott 1-night trip
Posted 21 hours ago
The Godfrey Hotel Boston

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! 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.

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.