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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Top Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Leavenworth Local Hotel
Room, 1 King Bed, Non Smoking | Premium bedding, down duvets, desk, laptop workspace

Leavenworth Local Hotel

2.5 star property
8.8 out of 10, Excellent, (329)
"Great Location very walkable "
The price is 2.580.561 ₫
3.032.160 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Leavenworth Local Hotel
Condotels
Front of property

Condotels

3.0 star property
9.0 out of 10, Wonderful, (185)
"Great location in a safe neighborhood. Love the walking trail and fountain nearby."
Condotels
Half Mi to Yacht Club: Home by Perry Lake!
House (3 Bedrooms) | Interior

Half Mi to Yacht Club: Home by Perry Lake!

3.0 star property
Half Mi to Yacht Club: Home by Perry Lake!
'the Farm House' w/ Deck & Historic Charm!
Interior

'the Farm House' w/ Deck & Historic Charm!

3.0 star property
'the Farm House' w/ Deck & Historic Charm!
Family-friendly Lansing Home With Covered Balcony!
House (3 Bedrooms) | Interior

Family-friendly Lansing Home With Covered Balcony!

3.0 star property
Family-friendly Lansing Home With Covered Balcony!
'the Vista' Retreat ~ 30 Mi to Kansas City!
Villa (5 Bedrooms) | Interior

'the Vista' Retreat ~ 30 Mi to Kansas City!

2.5 star property
'the Vista' Retreat ~ 30 Mi to Kansas City!
Spacious Ozawkie Home - Near Lake Perry!
House (4 Bedrooms) | Interior

Spacious Ozawkie Home - Near Lake Perry!

3.0 star property
Spacious Ozawkie Home - Near Lake Perry!
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

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like The Sallie House, or get outside and enjoy nature at Perry Lake. In the wider area, you’ll find Perry Lake Recreation Area and Delaware State Park.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.