Winchester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

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

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, (128)
"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
Lobby lounge
Global Luxury Suites Downtown Boston
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (617)
"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
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, (303)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is NT$2,921
NT$5,294 total
includes taxes & fees
Nov 16 - Nov 17
Temple Place Suites
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
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 16 - Nov 17
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
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
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
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, (305)
"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
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, (196)
"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$6,063
NT$12,249 total
includes taxes & fees
Nov 16 - Nov 17
Charlesgate Suites
First Floor 3-4 Bedrooms Apartment | Private kitchen | Fridge, microwave, coffee/tea maker, toaster
Apartments in Salem
Apartments in Salem
3.0 star property
8.0 out of 10, Very Good, (48)
"Property was fine. It is well located to see the sites in Salem. Only negative was that the neighbors were a bit loud at night. "
United States
Wes
Apartments in Salem
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
Apartment (1 Bedroom) | Interior
1 Mi to Downtown: Salem Vacation Rental!
1 Mi to Downtown: Salem Vacation Rental!
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great overall stay! "
United States
Tessa
The price is NT$3,919
NT$9,388 total
includes taxes & fees
Nov 17 - Nov 18
1 Mi to Downtown: Salem Vacation Rental!
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)
"Easy check in and clean property with in unit laundry"
United States
Sarah
The price is NT$5,759
NT$6,793 total
includes taxes & fees
Nov 16 - Nov 17
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Fishing
Brackett Cottage
Brackett Cottage
3.5 star property
10.0 out of 10, Exceptional, (2)
"Beautiful Home very clean and staff was very attentive to any needs or any comfort we needed,communication was A+ I highly recommend this beautiful home "
United States
Cristal
Brackett Cottage
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
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
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$4,960
NT$7,075 total
includes taxes & fees
Nov 26 - Nov 27
Global Luxury Suites East 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

The Revolution Hotel

The Revolution Hotel

10/10 Excellent
"Nice service. But the shawer Water is not hot enough. "
weihao 1-night trip
Posted 18 hours ago
The Revolution Hotel

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
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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.