Winchester Vacation Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winchester holiday rentals

Lobby lounge

Aparthotel in Chinatown

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (646 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, (156 reviews)
"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
Desk, iron/ironing board, free WiFi, bed sheets

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.0 out of 10, Good, (329 reviews)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is RM289
RM588 total
includes taxes & fees
19 Jan - 20 Jan
Temple Place Suites
42-inch TV with satellite channels

Aparthotel in South End

Maverick Suites at 400 Columbus Ave
2.0 star property
7.2 out of 10, Good, (135 reviews)
"everything was great! only thing i’ll say is that the dots have some cracks where people can see in on the bathrooms and some rooms, but other than that i’d start here again!"
United States
Maelynn
Maverick Suites at 400 Columbus Ave
Desk, laptop workspace, free WiFi, bed sheets

Aparthotel in Bay Village

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

Aparthotel in Beacon Hill

Maverick Suites at 40 Temple St
2.0 star property
7.6 out of 10, Good, (103 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
Iron/ironing board, free WiFi, bed sheets

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
6.2 out of 10, (257 reviews)
"We stayed there for four days. The heaters were not working, I got almost sick. And the customer service was awful. I hope you will find better place to stay"
United States
Aziza
Premier Suites - Bay Village
Living area

Aparthotel in South End

The Chester Hotel
4.0 star property
8.6 out of 10, Excellent, (28 reviews)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is RM475
RM1,269 total
includes taxes & fees
19 Jan - 20 Jan
The Chester Hotel
Interior

Apartment in South End

Furnished Apartment near BMC
3.0 star property
The price is RM580
RM1,227 total
includes taxes & fees
19 Jan - 20 Jan
Furnished Apartment near BMC
Front of property

Apartment in Fenway–Kenmore

Maverick Suites at 28 Fenway
3.0 star property
8.8 out of 10, Excellent, (335 reviews)
"Good place"
United States
Elijah
The price is RM383
RM837 total
includes taxes & fees
19 Jan - 20 Jan
Maverick Suites at 28 Fenway
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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Good"
Morgan 1-night trip
Posted 9 hours ago
Omni Boston Hotel at the Seaport

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. TD Garden and Fenway Park 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.