Search Holiday Rentals in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Top Holiday Rentals in Winchester

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

Aparthotel in Leavenworth

2.5 star property
8.8 out of 10, Excellent, (348)
"Enjoyed my stay"
United States
Luciana
The price is ₹9,151
₹10,752 total
includes taxes & fees
5 Jan - 6 Jan 2026
Leavenworth Local Hotel
Front of property
Condotels

Condo in Lansing

3.0 star property
9.0 out of 10, Wonderful, (188)
"Always a pleasant stay Friendly staff, clean rooms and great location "
United States
Leslie
The price is ₹10,799
₹12,570 total
includes taxes & fees
4 Jan - 5 Jan 2026
Condotels
House (3 Bedrooms) | Interior
Half Mi to Yacht Club: Home by Perry Lake!

Cottage in Meriden

3.0 star property
10.0 out of 10, Exceptional, (1)
"We came to the area for a tournament and this was our home base for the week—-warm, homey and a great retreat from the gym. We mostly had breakfasts there and then late night snacks. The beautiful country drive to both Topeka and Lawrence was easy. We appreciated the quiet area! "
United States
Gail
Half Mi to Yacht Club: Home by Perry Lake!
House (3 Bedrooms) | Interior
'the Farm House' w/ Deck & Historic Charm!

Cottage in Tonganoxie

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

Cottage in Lansing

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

Villa in Tonganoxie

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

Cottage in Ozawkie

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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Comfort Inn & Suites Lawrence - University Area

Comfort Inn & Suites Lawrence - University Area

10/10 Excellent
"Nice and big."
Francis 2-night trip
Posted 1 day ago
Comfort Inn & Suites Lawrence - University Area

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 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 Nell Hill's, or get outside and enjoy nature at Perry Lake. In the wider area, you’ll find Perry Lake Recreation Area and Ozawkie Township Hall.

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.