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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Winchester holiday rentals

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, (32 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is ₹17,608
₹32,340 total
includes taxes & fees
24 May - 25 May
The Chester Hotel
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, (376 reviews)
"Wonderful stay， convenient location "
United States
Junhu
The price is ₹11,541
₹19,316 total
includes taxes & fees
24 May - 25 May
Temple Place Suites
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, (116 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is ₹10,972
₹21,413 total
includes taxes & fees
25 May - 26 May
Maverick Suites at 40 Temple St
Front of property

Symple Live

Symple Live
4.0 star property
Fenway–Kenmore
The price is ₹19,216
₹31,488 total
includes taxes & fees
31 May - 1 Jun
Symple Live
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

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

10/10 Excellent
"Great location, spacious rooms and responsive staff."
mark 3-night trip
Posted less than an hour ago
Battery Wharf Hotel, Boston Waterfront

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
  • 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 Harbor. 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.