Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Winchester vacation rentals

Front of property
Maverick Suites at 40 Temple St

Aparthotel in Beacon Hill

2.0 star property
7.6 out of 10, Good, (102)
"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
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites

Aparthotel in Bay Village

2.0 star property
6.4 out of 10, (249)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Exterior
Maverick Suites at 245 Newbury St

Aparthotel in Back Bay

2.0 star property
8.2 out of 10, Very Good, (154)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites

Apartment in Downtown Boston

2.5 star property
7.0 out of 10, Good, (324)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is ￥13,980
￥25,890 total
includes taxes & fees
Dec 10 - Dec 11
Temple Place Suites
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Aparthotel in South End

2.0 star property
7.4 out of 10, Good, (133)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
Maverick Suites at 400 Columbus Ave
Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets
Maverick Suites at 28 Fenway

Apartment in Fenway–Kenmore

3.0 star property
8.8 out of 10, Excellent, (324)
"Good place"
United States
Elijah
The price is ￥13,545
￥30,792 total
includes taxes & fees
Dec 16 - Dec 17
Maverick Suites at 28 Fenway
Lobby lounge
Global Luxury Suites Downtown Boston

Aparthotel in Chinatown

4.0 star property
8.0 out of 10, Very Good, (628)
"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
Exterior
Best Location Studio In Downtown Boston

Apartment in Downtown Boston

10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
The price is ￥16,154
￥33,386 total
includes taxes & fees
Dec 12 - Dec 13
Best Location Studio In Downtown Boston
City Studio | Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel

Aparthotel in South End

4.0 star property
8.6 out of 10, Excellent, (28)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is ￥23,082
￥54,290 total
includes taxes & fees
Dec 15 - Dec 16
The Chester Hotel
Iron/ironing board, WiFi, bed sheets
The Chester: Hip, Renovated, South End

Apartment in South End

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice room. Good location "
United States
Abenamar A.
The price is ￥27,263
￥58,650 total
includes taxes & fees
Dec 14 - Dec 15
The Chester: Hip, Renovated, South End
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village

Aparthotel in Bay Village

2.0 star property
6.4 out of 10, (251)
"Clean room, good location, check in check out easily!"
United States
HIEN T
Premier Suites - Bay Village
TV, offices
Come Visit Boston and Stay In Our Homey Studio

Apartment in Downtown Boston

8.8 out of 10, Excellent, (3)
"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"
United States
Dean and Courtenay M.
The price is ￥16,154
￥33,386 total
includes taxes & fees
Dec 25 - Dec 26
Come Visit Boston and Stay In Our Homey Studio
1 bedroom, desk, iron/ironing board, WiFi
Studio Awaits Your Next Stay!

Apartment in Bay Village

9.2 out of 10, Wonderful, (5)
"Would stay again"
United States
mark p.
The price is ￥16,154
￥33,386 total
includes taxes & fees
Dec 18 - Dec 19
Studio Awaits Your Next Stay!
1 bedroom, WiFi
Modern North End Studio

Apartment in North End

9.0 out of 10, Wonderful, (10)
"Convenient location. Great restaurants. Perfect apatment for a couple. "
United States
Holly V.
The price is ￥19,416
￥48,745 total
includes taxes & fees
Dec 29 - Dec 30
Modern North End Studio
1 bedroom, desk, iron/ironing board, WiFi
Perfect One Bedroom Stay In Downtown Boston!

Apartment in Downtown Boston

8.6 out of 10, Excellent, (17)
"Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!"
United States
Christine
The price is ￥16,620
￥33,936 total
includes taxes & fees
Dec 10 - Dec 11
Perfect One Bedroom Stay In Downtown Boston!
1 bedroom, iron/ironing board, WiFi, bed sheets
Primo North End Studio

Apartment in North End

9.2 out of 10, Wonderful, (13)
"Accurate listing, very clean and comfortable. Perfect location to great food, history, and transportation."
United States
Anonymous traveler
The price is ￥17,916
￥46,563 total
includes taxes & fees
Dec 14 - Dec 15
Primo North End Studio
Fridge, microwave, oven, stovetop
North End Entire House

Apartment in North End

10.0 out of 10, Exceptional, (10)
"We stayed overnight to visit Snowport and then had a concert at TD garden. The location was perfect- a simple, quick walk to the venue! The house was extremely clean. The host was extremely communicative which made the trip even easier. . "
United States
Melissa
The price is ￥33,048
￥83,164 total
includes taxes & fees
Dec 10 - Dec 11
North End Entire House
Smart TV, fireplace
2BR Historic Marblehead Home+Minutes to Beach

Vacation Home in Marblehead

2.0 star property
10.0 out of 10, Exceptional, (18)
"Enjoyed our stay. "
United States
Mary D.
The price is ￥14,531
￥53,881 total
includes taxes & fees
Dec 10 - Dec 11
2BR Historic Marblehead Home+Minutes to Beach
2 bedrooms, iron/ironing board, travel crib, WiFi
Back-Bay Lux Central 2BR Condo with Rooftop and Parking

Apartment in Bay Village

10.0 out of 10, Exceptional, (4)
"Great space, location is close to a ton of shopping. Good safe area! 20 minute walk to TD Garden which isn’t bad"
United States
Dillon F.
The price is ￥30,911
￥130,400 total
includes taxes & fees
Dec 10 - Dec 11
Back-Bay Lux Central 2BR Condo with Rooftop and Parking
Terrace/patio
Back-Bay Upscale Central Condo Bos Common Downtown

Condo in Bay Village

10.0 out of 10, Exceptional, (10)
"Great place close to restaurants and shopping! Coffee bar in the lobby with concierge services. Would come back again. "
United States
Shelley K.
The price is ￥30,911
￥120,244 total
includes taxes & fees
Dec 10 - Dec 11
Back-Bay Upscale Central Condo Bos Common Downtown
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

Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

10/10 Excellent
"Staff is very friendly and accommodating. Room was clean and the bed was comfortable. Breakfast was very good."
Geraldine 1-night trip
Posted 20 hours ago
Wyndham Boston Beacon Hill

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:

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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 are some of the best vacation home rentals in Winchester?

Cozy Salem Getaway. Historic Home Near All the Sights: This vacation home rental outside of Winchester offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Harvard Square 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.