Search Holiday Rentals in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

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

Quincy Home on Lavender Farm w/ River Views!
House (3 Bedrooms) | Interior

Quincy Home on Lavender Farm w/ River Views!

3.0 star property
Quincy Home on Lavender Farm w/ River Views!
Lovely Crescent Bar Condo w/ Community Amenities!
Apartment (1 Bedroom) | Front of property

Lovely Crescent Bar Condo w/ Community Amenities!

3.5 star property
Lovely Crescent Bar Condo w/ Community Amenities!
Columbia Pool House in Quincy
House, Accessible | 4 bedrooms

Columbia Pool House in Quincy

2.0 star property
Columbia Pool House in Quincy
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.
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

Best Western Rama Inn

Best Western Rama Inn

10/10 Excellent
"Everything excellent 👌 "
Sergej 1-night trip
Posted 1 day ago
Best Western Rama Inn

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 can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Quincy Aquatic Center, or get outside and enjoy nature at Soap Lake Park. Soap Lake and Moses Lake are a couple of places you'll find in the wider 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 provide amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family trips.