A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Winchester holiday rentals

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, (307 reviews)
"Great location and well maintained"
United States
EDDIE
The price is RM494
RM780 total
includes taxes & fees
27 Jul - 28 Jul
Premier Suites - Bay Village
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, (186 reviews)
"great place and great location! would love to stay again!!"
United States
Hailey
The price is RM659
RM1,135 total
includes taxes & fees
27 Jul - 28 Jul
Maverick Suites at 245 Newbury St
Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (34 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is RM778
RM1,413 total
includes taxes & fees
22 Jul - 23 Jul
The Chester Hotel
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, (412 reviews)
"Hotel was exactly as described. Great value for a quick trip to Boston."
United States
Eileen
The price is RM494
RM827 total
includes taxes & fees
26 Jul - 27 Jul
Temple Place Suites
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,230 reviews)
"Hotel exceeded expectations, very clean inside and out. Friendly staff"
United States
James
The price is RM660
RM737 total
includes taxes & fees
23 Jul - 24 Jul
Crescent Suites Hotel
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (159 reviews)
"Well located"
United States
Evelyn
The price is RM676
RM1,060 total
includes taxes & fees
22 Jul - 23 Jul
Maverick Suites at 400 Columbus Ave
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (389 reviews)
"Everything was perfect"
United States
Catherine
The price is RM659
RM1,158 total
includes taxes & fees
26 Jul - 27 Jul
Maverick Suites at 28 Fenway
Interior entrance

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (300 reviews)
"Great location super close to great restaurants and shopping. I've stayed at this location a couple of times and it never disappoints!"
United States
Melissa
The price is RM557
RM988 total
includes taxes & fees
22 Jul - 23 Jul
Maverick Suites at 89 Marion
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
"Loved this hotel, I arrived early and was not expecting to check in, but they said the room was available. The room was beautiful and very inviting. Also, had easy access to a bus to take me to the airport. Great location."
Mary 1-night trip
Posted less than an hour ago
Seaport 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
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  • 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!

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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.

How many holiday rentals are there in Winchester?

Choose from 3 Expedia holiday rentals in Winchester for a memorable holiday.

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.