Winchester Vacation Rentals

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Check prices for these dates

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

Vacation Rentals in Winchester

Our top choices for Winchester vacation rentals

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

Leavenworth Local Hotel

2.5 star property
8.8 out of 10, Excellent, (329)
"Great Location very walkable "
The price is NT$2,987
NT$3,509 total
includes taxes & fees
Sep 1 - Sep 2
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

Find out more about Winchester

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! 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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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we have vacation rentals close to the most popular attractions in Winchester, or you can go with a more remote 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 larger area, you’ll find Perry Lake Recreation Area and Delaware State Park.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winchester. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family getaway.