Winchester Vacation Rentals

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
This weekend
Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Vacation Rentals in Winchester

Temple Place Suites
1 bedroom, desk, iron/ironing board, free WiFi

Temple Place Suites

2.5 star property
7.0 out of 10, Good, (278)
"Very convenient place to stay, near transportation and waking distance to historic points and shopping. "
The price is P7,321
P12,089 total
includes taxes & fees
Oct 5 - Oct 6
Temple Place Suites
Bay Village Suites
Desk, laptop workspace, free WiFi, bed sheets

Bay Village Suites

2.0 star property
6.4 out of 10, (223)
"Great Location!! "
Bay Village Suites
Crescent Suites Hotel
Property grounds

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (1098)
"The staff were friendly and the accommodation was good"
The price is P8,838
P9,872 total
includes taxes & fees
Oct 26 - Oct 27
Crescent Suites Hotel
Global Luxury Suites Downtown Boston
Lobby lounge

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (605)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
Global Luxury Suites Downtown Boston
Premier Suites - Bay Village
Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

2.0 star property
6.4 out of 10, (226)
"Clean room, good location, check in check out easily!"
The price is P10,052
P14,561 total
includes taxes & fees
Nov 2 - Nov 3
Premier Suites - Bay Village
Maverick Suites at 28 Fenway
1 bedroom, individually furnished, iron/ironing board, free WiFi

Maverick Suites at 28 Fenway

3.0 star property
8.8 out of 10, Excellent, (284)
"Great location"
The price is P7,408
P14,193 total
includes taxes & fees
Oct 28 - Oct 29
Maverick Suites at 28 Fenway
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Lobby

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very Good, (525)
"beautiful stay"
The price is P11,804
P13,687 total
includes taxes & fees
Nov 2 - Nov 3
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Maverick Suites at 89 Marion
Interior entrance

Maverick Suites at 89 Marion

2.0 star property
8.4 out of 10, Very Good, (257)
"I liked the location very much! "
The price is P7,557
P13,633 total
includes taxes & fees
Nov 3 - Nov 4
Maverick Suites at 89 Marion
The Chester Hotel
1 bedroom, Egyptian cotton sheets, premium bedding, memory foam beds

The Chester Hotel

4.0 star property
8.8 out of 10, Excellent, (22)
"The property was spacious and clean. We enjoyed our stay!"
The price is P10,354
P22,255 total
includes taxes & fees
Nov 3 - Nov 4
The Chester Hotel
Maverick Suites at 245 Newbury St
Exterior

Maverick Suites at 245 Newbury St

2.0 star property
8.2 out of 10, Very Good, (147)
"Clean. Great location. "
The price is P12,446
P19,650 total
includes taxes & fees
Oct 30 - Oct 31
Maverick Suites at 245 Newbury St
Maverick Suites at 40 Temple St
Front of property

Maverick Suites at 40 Temple St

2.0 star property
7.4 out of 10, Good, (94)
"Great location "
The price is P8,001
P14,541 total
includes taxes & fees
Nov 3 - Nov 4
Maverick Suites at 40 Temple St
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
View from property

Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

3.5 star property
8.8 out of 10, Excellent, (72)
"Great place , size of the apartment , very clean"
The price is P18,719
P22,079 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Global Luxury Suites East Boston
Rooftop terrace

Global Luxury Suites East Boston

4.0 star property
7.0 out of 10, Good, (165)
"I don’t know why this place has gotten some bad reviews. This was a great stay. Clean, safe, very convenient. It’s right across the street from the ferry that takes you across the harbor to long wharf or seaport district. And also a close walk to the subway. The apartment itself was beautiful. Loved it. The indoor pool was great especially for the couple of rainy days we had during our visit. Such a great stay!"
The price is P15,155
P24,100 total
includes taxes & fees
Oct 29 - Oct 30
Global Luxury Suites East Boston
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Property amenity

Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway

4.0 star property
8.8 out of 10, Excellent, (268)
"Check in staff was amazing! Love the apartment and location!"
The price is P13,039
P15,379 total
includes taxes & fees
Oct 29 - Oct 30
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
Individually furnished, laptop workspace, iron/ironing board, bed sheets

No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

4.0 star property
9.2 out of 10, Wonderful, (938)
"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 "
The price is P16,211
P19,121 total
includes taxes & fees
Oct 5 - Oct 6
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
The Monty Boston
Living area

The Monty Boston

2.5 star property
9.2 out of 10, Wonderful, (22)
"Everything was great to live in this place! Very spacious and convenient."
The price is P35,509
P50,836 total
includes taxes & fees
Oct 15 - Oct 16
The Monty Boston
Maverick Suites at 400 Columbus Ave
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

2.0 star property
7.2 out of 10, Good, (122)
"I encountered difficulty — frustratingly so — trying to get the hotel room door to open based on the code."
The price is P6,075
P12,326 total
includes taxes & fees
Nov 3 - Nov 4
Maverick Suites at 400 Columbus Ave
Maverick Suites at 402 Columbus Ave
Private kitchen

Maverick Suites at 402 Columbus Ave

2.5 star property
7.8 out of 10, Good, (61)
"Easy to walk to and from T stations near by. Decently priced and was overall a great place to stay!"
The price is P8,297
P14,881 total
includes taxes & fees
Nov 2 - Nov 3
Maverick Suites at 402 Columbus Ave
Charlesgate Suites
1 bedroom, premium bedding, desk, iron/ironing board

Charlesgate Suites

3.5 star property
9.4 out of 10, Exceptional, (191)
"Awesome property, conveniently located near everything, especially Fenway. Definitely will stay here again. "
The price is P13,364
P25,381 total
includes taxes & fees
Oct 5 - Oct 6
Charlesgate Suites
Furnished Apartments near Encore Boston
1 bedroom, desk, laptop workspace, free WiFi

Furnished Apartments near Encore Boston

2.5 star property
8.0 out of 10, Very Good, (4)
"Great place. Very clean. Great communication."
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

Hilton Boston Logan Airport

Hilton Boston Logan Airport

10/10 Excellent
"Great"
Jo Anne 1-night trip
Posted 11 hours ago
Hilton Boston Logan Airport

Find out more about Winchester

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.