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

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winchester holiday rentals

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up)

1. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, 469, (469 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is Rp2.425.035
Rp3.900.989 total
includes taxes & fees
20 Sept - 21 Sept
Temple Place Suites
Studio

2. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.8 out of 10, 22, (22 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is Rp5.214.617
Rp8.221.025 total
includes taxes & fees
20 Sept - 21 Sept
The Concord Hotel
Lobby

3. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, 315, (315 reviews)
"Everything is good"
United States
Kilyen
The price is Rp2.773.732
Rp5.010.351 total
includes taxes & fees
20 Sept - 21 Sept
Kasa Boston at Fenway
Front of property

4. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, 146, (146 reviews)
"Worth the stay"
Canada
Akansha
The price is Rp3.411.691
Rp5.541.246 total
includes taxes & fees
20 Sept - 21 Sept
Maverick Suites at 40 Temple St
Premium Apartment | Living area

5. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, 38, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is Rp3.930.775
Rp6.745.248 total
includes taxes & fees
30 Sept - 1 Oct
The Chester Hotel
Exterior

6. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, 202, (202 reviews)
"Great location, really cool place!"
United States
lane
The price is Rp3.803.976
Rp5.992.179 total
includes taxes & fees
20 Sept - 21 Sept
Maverick Suites at 245 Newbury St
Deluxe Double Room, Shared Bathroom

7. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, 340, (340 reviews)
"Location is great"
United States
Eria
The price is Rp2.631.083
Rp3.935.404 total
includes taxes & fees
5 Oct - 6 Oct
Premier Suites - Bay Village
Living area

8. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, 171, (171 reviews)
"Well located"
United States
Evelyn
The price is Rp2.567.684
Rp4.571.060 total
includes taxes & fees
20 Sept - 21 Sept
Maverick Suites at 400 Columbus Ave
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Room was clean, air conditioning was perfect, staff was nice and helpful 👌"
NINA 3-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Find out more about Winchester

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

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Griffin Photography Museum, 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. 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.