Winchester Vacation Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Winchester holiday rentals

Interior

1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown Salem: Studio w/ Fire Pit Access
3.0 star property
Salem
9.6 out of 10, Exceptional, (5 reviews)
"Studio was very nicely laid out and the owner of the property was friendly! Area the house was in was quiet but yet still walkable to downtown Salem. Bagel place across the street was amazing as well"
United States
chris
The price is RM534
RM1,393 total
includes taxes & fees
28 Apr - 29 Apr
1 Mi to Downtown Salem: Studio w/ Fire Pit Access
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, (354 reviews)
"Wonderful stay， convenient location "
United States
Junhu
The price is RM477
RM798 total
includes taxes & fees
21 Apr - 22 Apr
Temple Place Suites
Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is RM740
RM1,555 total
includes taxes & fees
21 Apr - 22 Apr
The Chester Hotel
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, (350 reviews)
"Clean"
United States
Kristin
The price is RM406
RM852 total
includes taxes & fees
21 Apr - 22 Apr
Maverick Suites at 28 Fenway
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, (109 reviews)
"Very quiet, great location. "
United States
Cole
The price is RM615
RM1,071 total
includes taxes & fees
21 Apr - 22 Apr
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, (162 reviews)
"Great location, clean and great 😌 "
United States
Catherine
The price is RM637
RM1,095 total
includes taxes & fees
22 Apr - 23 Apr
Maverick Suites at 245 Newbury St
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 Parker House

Omni Parker House

8/10 Good
"Clean room, Che led on early great breakfasts "
elliott 2-night trip
Posted 3 hours ago
Omni Parker House

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:

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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. 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.