Winchester Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Winchester holiday rentals

Rooftop terrace

Condo resort in Downtown Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
9.4 out of 10, Exceptional, (623 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 HK$2,187
HK$2,514 total
includes taxes & fees
22 Mar - 23 Mar
Marriott Vacation Club® at Custom House, Boston
Interior

Apartment in South End

Furnished Apartment near BMC
3.0 star property
6.0 out of 10, (1 review)
The price is HK$1,387
HK$2,676 total
includes taxes & fees
21 Mar - 22 Mar
Furnished Apartment near BMC
Interior

Apartment in Lynn

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
The price is HK$525
HK$2,390 total
includes taxes & fees
23 Mar - 24 Mar
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
Lobby lounge

Aparthotel in Chinatown

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (669 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
Global Luxury Suites Downtown Boston
Exterior

Aparthotel in Back Bay

Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (160 reviews)
"Great location, clean and great 😌 "
United States
Catherine
Maverick Suites at 245 Newbury St
Desk, iron/ironing board, free WiFi, bed sheets

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.2 out of 10, Good, (336 reviews)
"Very spacious"
United States
Melany
The price is HK$727
HK$1,331 total
includes taxes & fees
20 Mar - 21 Mar
Temple Place Suites
Desk, laptop workspace, free WiFi, bed sheets

Aparthotel in Bay Village

Bay Village Suites
2.0 star property
6.6 out of 10, (257 reviews)
"This is a convenient property, close to the T and the Common. You will need to be able to walk up some narrow stairs, and adjust to sharing a common bathroom. I met the owner while he was shoveling snow after the nor'easter, and he could not have been nicer! Great value for the money, fairly quiet and I would stay again."
United States
Louise
The price is HK$1,050
HK$1,613 total
includes taxes & fees
8 Apr - 9 Apr
Bay Village Suites
Iron/ironing board, free WiFi, bed sheets

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (259 reviews)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is HK$1,292
HK$1,891 total
includes taxes & fees
16 Apr - 17 Apr
Premier Suites - Bay Village
42-inch TV with satellite channels

Aparthotel in South End

Maverick Suites at 400 Columbus Ave
2.0 star property
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
Maverick Suites at 400 Columbus Ave
Front of property

Aparthotel in Beacon Hill

Maverick Suites at 40 Temple St
2.0 star property
7.6 out of 10, Good, (104 reviews)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
Maverick Suites at 40 Temple St
Premium bedding, desk, iron/ironing board, free WiFi

Aparthotel in Fenway–Kenmore

Charlesgate Suites
3.5 star property
9.4 out of 10, Exceptional, (202 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 HK$1,348
HK$2,901 total
includes taxes & fees
24 Mar - 25 Mar
Charlesgate Suites
Living area

Aparthotel in South End

The Chester Hotel
4.0 star property
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is HK$962
HK$2,503 total
includes taxes & fees
24 Mar - 25 Mar
The Chester Hotel
Interior

Apartment in Salem

1 Mi to Downtown: Salem Vacation Rental!
3.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Great overall stay! "
United States
Tessa
The price is HK$909
HK$2,863 total
includes taxes & fees
22 Mar - 23 Mar
1 Mi to Downtown: Salem Vacation Rental!
Front of property

Apartment in Fenway–Kenmore

Maverick Suites at 28 Fenway
3.0 star property
8.6 out of 10, Excellent, (339 reviews)
"Good place"
United States
Elijah
The price is HK$783
HK$1,666 total
includes taxes & fees
22 Mar - 23 Mar
Maverick Suites at 28 Fenway
Living area

Aparthotel in Downtown Boston

The Monty Boston
2.5 star property
9.6 out of 10, Exceptional, (34 reviews)
"Amazing property, would stay again."
United States
Doug
The price is HK$4,162
HK$6,136 total
includes taxes & fees
30 Mar - 31 Mar
The Monty Boston
Living area

Apartment in East Somerville

3 bd 2 ba Unit
3.0 star property
The price is HK$2,800
HK$4,303 total
includes taxes & fees
20 Mar - 21 Mar
3 bd 2 ba Unit
2 bedrooms, desk

Apartment in Swampscott

Coastal Charm Lobster Ch Teau
2.0 star property
The price is HK$1,924
HK$5,630 total
includes taxes & fees
26 Mar - 27 Mar
Coastal Charm Lobster Ch Teau
1 bedroom, iron/ironing board, free cots/infant beds, rollaway beds

Apartment in Salem

Apartments in Salem
3.0 star property
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 HK$1,283
HK$2,604 total
includes taxes & fees
22 Mar - 23 Mar
Apartments in Salem
1 bedroom, desk, laptop workspace, free WiFi

Aparthotel in Everett

Furnished Apartments near Encore Boston
2.5 star property
8.8 out of 10, Excellent, (13 reviews)
"The apartment was nice and very spacious. "
United States
Scott
The price is HK$1,521
HK$2,574 total
includes taxes & fees
21 Mar - 22 Mar
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

citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Clean room but very cold staff was nice heat was very low we had to call twice but in the end they fixed it , I must say it was during the storm so temperatures were veryyy low "
Gentiana 1-night trip
Posted 2 hours ago
citizenM Boston Back Bay

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 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 are some of the best holiday rentals that Winchester has to offer?

Spacious, New Renovation | Near T: This holiday home rental outside of Winchester is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 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.