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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Winchester holiday rentals

42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
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
Exterior
Maverick Suites at 245 Newbury St

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, (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
Lobby lounge
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (636)
"Very clean, beautiful place. I would stay there again."
Canada
Liam
Global Luxury Suites Downtown Boston
Front of property
Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
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

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (252)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Front of property
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (326)
"Good place"
United States
Elijah
The price is RM348
RM798 total
includes taxes & fees
24 Dec - 25 Dec
Maverick Suites at 28 Fenway
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (252)
"Clean room, good location, check in check out easily!"
United States
HIEN T
Premier Suites - Bay Village
Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201)
"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 RM619
RM1,413 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charlesgate Suites
Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (326)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is RM366
RM679 total
includes taxes & fees
24 Dec - 25 Dec
Temple Place Suites
Exterior
Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68)
"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
Maverick Suites at 402 Columbus Ave
1 bedroom, desk, laptop workspace, free WiFi
Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.4 out of 10, Very good, (8)
"Great place. Very clean. Great communication."
United States
Michele
Furnished Apartments near Encore Boston
Interior entrance
Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
8.2 out of 10, Very good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
Maverick Suites at 89 Marion
Living area
The Chester Hotel

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is RM608
RM1,424 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Chester Hotel
1 bedroom, iron/ironing board, free cots/infant beds, rollaway beds
Apartments in Salem

Apartments in Salem

Apartments in Salem
3.0 star property
Salem
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
Indoor pool, pool umbrellas, pool loungers
Global Luxury Suites East Boston

Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
7.0 out of 10, Good, (177)
"The place was very nice and nicely equipped, but a little difficult to locate."
United States
William
The price is RM501
RM759 total
includes taxes & fees
29 Dec - 30 Dec
Global Luxury Suites East Boston
Living area
The Monty Boston

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (29)
"Amazing property, would stay again."
United States
Doug
The price is RM2,079
RM3,092 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Monty Boston
Interior
1 Mi to Downtown: Salem Vacation Rental!

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, (2)
"Great overall stay! "
United States
Tessa
The price is RM472
RM1,342 total
includes taxes & fees
24 Dec - 25 Dec
1 Mi to Downtown: Salem Vacation Rental!
Terrace/patio
Crescent Suites Hotel

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1144)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel
2 bedrooms, desk
Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is RM1,286
RM3,256 total
includes taxes & fees
6 Jan - 7 Jan 2026
Coastal Charm Lobster Ch Teau
Exterior
Broom & Board

Broom & Board

Broom & Board
3.5 star property
Salem
10.0 out of 10, Exceptional, (1)
"Great stay highly recommended!"
United States
Jamie
Broom & Board
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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Great place to stay"
Nick A 4-night trip
Posted 1 day ago
The Godfrey Hotel Boston

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia.co.uk! 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 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.