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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Winchester holiday rentals

Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (655 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
The price is ₹6,172
₹11,207 total
includes taxes & fees
2 Feb - 3 Feb
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
7.2 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
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, (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
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, (157 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
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
7.0 out of 10, Good, (331 reviews)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is ₹8,255
₹15,288 total
includes taxes & fees
2 Feb - 3 Feb
Temple Place Suites
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, (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
Desk, laptop workspace, free WiFi, bed sheets

Bay Village Suites

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

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (335 reviews)
"Good place"
United States
Elijah
The price is ₹8,668
₹18,926 total
includes taxes & fees
1 Feb - 2 Feb
Maverick Suites at 28 Fenway
Exterior

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 reviews)
"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
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, (201 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 ₹13,942
₹31,842 total
includes taxes & fees
2 Feb - 3 Feb
Charlesgate Suites
Interior entrance

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, (271 reviews)
"Great location for getting off and on the train and clean. We were on the first floor and it was very loud. You would hear people up and down the stairs. And if you have people staying in the room above you, you can hear everything. "
United States
samantha
Maverick Suites at 89 Marion
Indoor pool, pool umbrellas, pool loungers

Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
7.0 out of 10, Good, (178 reviews)
"The place was very nice and nicely equipped, but a little difficult to locate."
United States
William
The price is ₹9,411
₹14,930 total
includes taxes & fees
1 Feb - 2 Feb
Global Luxury Suites East Boston
Classic Apartment, 3rd floor 3 Bedrooms | 1 bedroom, iron/ironing board, free cots/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
Apartments in Salem
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, (2 reviews)
"Great overall stay! "
United States
Tessa
The price is ₹10,640
₹33,505 total
includes taxes & fees
2 Feb - 3 Feb
1 Mi to Downtown: Salem Vacation Rental!
Apartment, 2 Bedrooms | Interior

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
The price is ₹13,655
₹28,358 total
includes taxes & fees
30 Jan - 31 Jan
Furnished Apartment near BMC
Luxury Suite 2 | 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, (31 reviews)
"Amazing property, would stay again."
United States
Doug
The price is ₹43,835
₹66,203 total
includes taxes & fees
10 Feb - 11 Feb
The Monty Boston
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
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 ₹14,529
₹33,044 total
includes taxes & fees
30 Jan - 31 Jan
The Chester Hotel
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,150 reviews)
"Everything about this facility was pleasing: clean, well-appointed, great kitchen, comfortable, well-located in the area. We were given a warm welcome when we arrived, provided with lots of information about Waltham. Located near shops and restaurants and on a walking trail along the Charles River. Highly recommend and would stay here again. "
Canada
Susan
Crescent Suites Hotel
Apartment | 1 bedroom, desk, laptop workspace, free WiFi

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.4 out of 10, Very good, (10 reviews)
"Great place. Very clean. Great communication."
United States
Michele
The price is ₹10,574
₹22,064 total
includes taxes & fees
30 Jan - 31 Jan
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

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Wonderful staff and great experience! "
Jamie 1-night trip
Posted 23 hours ago
Seaport Hotel Boston

Find out more about Winchester

Holiday Rentals in 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
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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.