Winchester Vacation Rentals

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Check prices for these dates

Tonight
Oct 29 - Oct 30
Tomorrow
Oct 30 - Oct 31
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Winchester

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, (302)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is NT$2,921
NT$5,294 total
includes taxes & fees
Nov 18 - Nov 19
Temple Place Suites
Property grounds
Crescent Suites Hotel
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (1118)
"Great Hotel. Super friendly staff."
United States
Michael
Crescent Suites Hotel
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village
Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (240)
"Clean room, good location, check in check out easily!"
United States
HIEN T
Premier Suites - Bay Village
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites
Bay Village Suites
2.0 star property
6.6 out of 10, (237)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
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, (304)
"great location"
United States
Mario
The price is NT$2,967
NT$6,402 total
includes taxes & fees
Nov 25 - Nov 26
Maverick Suites at 28 Fenway
Lobby
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
4.0 star property
8.2 out of 10, Very Good, (533)
"Friendly service, great location and design. "
United States
Johannes
The price is NT$4,106
NT$4,761 total
includes taxes & fees
Nov 23 - Nov 24
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Lobby lounge
Global Luxury Suites Downtown Boston
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (616)
"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
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 NT$3,409
NT$6,544 total
includes taxes & fees
Nov 24 - Nov 25
Maverick Suites at 89 Marion
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, (946)
"I was pleasantly surprised with how easy this stay was. the location was perfect and the access was super easy. will definitely recommend and stay again. "
United States
Christina
The price is NT$5,208
NT$6,143 total
includes taxes & fees
Nov 23 - Nov 24
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
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, (127)
"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 NT$2,811
NT$6,047 total
includes taxes & fees
Nov 25 - Nov 26
Maverick Suites at 400 Columbus Ave
Rooftop terrace
Global Luxury Suites East Boston
Global Luxury Suites East Boston
4.0 star property
6.8 out of 10, (170)
"I will not be staying there again. "
United States
Malcolm
The price is NT$4,976
NT$7,098 total
includes taxes & fees
Nov 26 - Nov 27
Global Luxury Suites East Boston
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, (274)
"Check in staff was amazing! Love the apartment and location!"
United States
Tina
The price is NT$5,759
NT$6,793 total
includes taxes & fees
Nov 23 - Nov 24
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Front of property
Maverick Suites at 40 Temple St
Maverick Suites at 40 Temple St
2.0 star property
7.6 out of 10, Good, (101)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
The price is NT$3,878
NT$7,273 total
includes taxes & fees
Nov 25 - Nov 26
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 NT$4,320
NT$7,782 total
includes taxes & fees
Nov 25 - Nov 26
Maverick Suites at 245 Newbury St
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 NT$5,456
NT$11,727 total
includes taxes & fees
Nov 6 - Nov 7
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
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 NT$2,811
NT$6,047 total
includes taxes & fees
Nov 25 - Nov 26
Maverick Suites at 402 Columbus Ave
Apartment | 1 bedroom, premium bedding, desk, iron/ironing board
Charlesgate Suites
Charlesgate Suites
3.5 star property
9.4 out of 10, Exceptional, (195)
"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 NT$7,440
NT$13,832 total
includes taxes & fees
Nov 9 - Nov 10
Charlesgate Suites
View from property
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
3.5 star property
8.8 out of 10, Excellent, (77)
"Excellent location in the heart of shops. Quiet and clean location. Highly recommend and would definitely stay again ❤️."
United States
Michelle
The price is NT$7,578
NT$8,938 total
includes taxes & fees
Nov 25 - Nov 26
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services
The Monty Boston
The Monty Boston
2.5 star property
9.4 out of 10, Exceptional, (26)
"Beautiful and comfortable. Plenty of room and good location. "
United States
Mary
The price is NT$17,175
NT$25,022 total
includes taxes & fees
Nov 5 - Nov 6
The Monty Boston
Apartment | 1 bedroom, desk, laptop workspace, free WiFi
Furnished Apartments near Encore Boston
Furnished Apartments near Encore Boston
2.5 star property
8.4 out of 10, Very Good, (6)
"Great place. Very clean. Great communication."
United States
Michele
The price is NT$6,644
NT$10,842 total
includes taxes & fees
Oct 30 - Oct 31
Furnished Apartments near Encore Boston
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

Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport

10/10 Excellent
"Checkin was quick, the room and beds very comfortable, great breakfast choices in the morning, and a convenient shuttle to Logan. Perfect!!"
Susan 1-night trip
Posted 10 hours ago
Hampton Inn Boston - Logan Airport

Find out more about Winchester

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Winter Pond, or you can choose a more remote option if you're looking for a relaxing stay. Winchester is known for its soccer 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 vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.