Winchester Vacation Rentals

  • 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

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Winchester vacation rentals

Rooftop terrace

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (628 reviews)
"Hotel is in the perfect area to go to Faneuil hall as well as to the north end everything’s in walking distance multiple restaurants you can eat high-end or very inexpensive fun time for all"
United States
Cathy
The price is ₩483,902
₩556,244 total
includes taxes & fees
May 3 - May 4
Marriott Vacation Club® at Custom House, Boston
Apartment (1 Bedroom) | Interior

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is ₩100,641
₩458,126 total
includes taxes & fees
Apr 26 - Apr 27
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
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, (106 reviews)
"Very quiet, great location. "
United States
Cole
The price is ₩250,076
₩423,380 total
includes taxes & fees
Apr 12 - Apr 13
Maverick Suites at 40 Temple St
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (680 reviews)
"Great staff, clean, and location"
United States
Juan
The price is ₩321,750
₩437,191 total
includes taxes & fees
Apr 12 - Apr 13
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
South End
7.4 out of 10, Good, (136 reviews)
"I couldn’t quite get the plug in stove to work. But overall it was an alright stay!!"
United States
Myah
The price is ₩151,642
₩310,231 total
includes taxes & fees
Apr 14 - Apr 15
Maverick Suites at 400 Columbus Ave
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is ₩231,453
₩529,392 total
includes taxes & fees
Apr 15 - Apr 16
The Chester Hotel
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (348 reviews)
"Wonderful stay， convenient location "
United States
Junhu
The price is ₩178,246
₩298,334 total
includes taxes & fees
Apr 22 - Apr 23
Temple Place Suites
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (205 reviews)
"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 ₩276,384
₩572,558 total
includes taxes & fees
Apr 12 - Apr 13
Charlesgate Suites
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, (162 reviews)
"Great location, clean and great 😌 "
United States
Catherine
The price is ₩225,766
₩397,651 total
includes taxes & fees
Apr 13 - Apr 14
Maverick Suites at 245 Newbury St
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (262 reviews)
"AMAZING!!! Do NOT listen to all of the negative reviews. When I first found this listing I was really unsure because there was so many bad reviews. I took a chance and booked anyway. The stay was phenomenal. Check in was super easy and the company/host was very responsive. Very close to train station as well. They sent text messages and even let us know the room was ready for check in around 2pm instead of waiting until 4pm check in. The room was super clean and nice. No issues with anything....
United States
Amaya
The price is ₩139,244
₩237,762 total
includes taxes & fees
Apr 14 - Apr 15
Premier Suites - Bay Village
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (343 reviews)
"Clean"
United States
Kristin
The price is ₩158,171
₩328,585 total
includes taxes & fees
Apr 14 - Apr 15
Maverick Suites at 28 Fenway
Apartment (1 Bedroom) | Interior

1 Mi to Downtown: Salem Vacation Rental!

1 Mi to Downtown: Salem Vacation Rental!
3.0 star property
Salem
10.0 out of 10, Exceptional, (3 reviews)
"Great overall stay! "
United States
Tessa
The price is ₩171,447
₩539,880 total
includes taxes & fees
Apr 12 - Apr 13
1 Mi to Downtown: Salem Vacation Rental!
Apartment | 2 bedrooms, desk

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is ₩335,056
₩969,662 total
includes taxes & fees
Apr 10 - Apr 11
Coastal Charm Lobster Ch Teau
Luxury Suite 3 | Living area | Smart TV, Netflix, Hulu, streaming services

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (36 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is ₩1,046,417
₩1,457,712 total
includes taxes & fees
Apr 27 - Apr 28
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
Everett
8.8 out of 10, Excellent, (13 reviews)
"The apartment was nice and very spacious. "
United States
Scott
The price is ₩289,905
₩491,609 total
includes taxes & fees
Apr 10 - Apr 11
Furnished Apartments near Encore Boston
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,163 reviews)
"Excellent customer service, fantastic facilities, everything was in the room, refrigerator, oven, etc"
United States
Jose
The price is ₩211,500
₩236,245 total
includes taxes & fees
Apr 30 - May 1
Crescent Suites Hotel
Condo (The Warlock House) | Exterior

The Warlock House

The Warlock House
3.0 star property
Salem
The price is ₩845,898
₩1,459,160 total
includes taxes & fees
Apr 12 - Apr 13
The Warlock House
Interior entrance

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very Good, (277 reviews)
"The room was very clean and perfectly sized for a solo traveler for several nights."
United States
Valeri
The price is ₩144,653
₩295,805 total
includes taxes & fees
Apr 14 - Apr 15
Maverick Suites at 89 Marion
Classic Apartment, 3rd floor 3 Bedrooms | 1 bedroom, iron/ironing board, free cribs/infant beds, rollaway beds

Apartments in Salem

Apartments in Salem
3.0 star property
Salem
8.0 out of 10, Very Good, (48 reviews)
"The whole floor was clean and organized. The whole floor also felt inviting and comforting. We enjoyed how close we where to everthing. We were both so happy with found this apartment. "
United States
Jason
The price is ₩328,114
₩587,255 total
includes taxes & fees
Apr 12 - Apr 13
Apartments in Salem
Exterior

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, (69 reviews)
"Easy to walk to and from T stations near by. Decently priced and was overall a great place to stay!"
United States
Jordan
The price is ₩181,153
₩346,368 total
includes taxes & fees
Apr 12 - Apr 13
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.
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 Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

8/10 Good
"I am not sure what was served for breakfast. We didn’t see anything but apple. "
Luciana 2-night trip
Posted 1 hour ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Winchester

Search for Vacation rentals in Winchester on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Winchester using one of the methods below:

  • View our selection of featured Vacation rentals in Winchester
  • Use the map to find apartments and other Vacation homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation 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. Fenway Park and Encore Boston Harbor 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.