Photo by Betsy Wood

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

Tonight
24 Jun - 25 Jun
Tomorrow
25 Jun - 26 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Holiday Rentals in Winchester

The Cottages at Golden Village Palms RV Resort
3 outdoor pools, pool umbrellas, pool loungers

The Cottages at Golden Village Palms RV Resort

3.0 star property
9.4 out of 10, Exceptional, (61)
"So embarrassing. Easter weekend my husband and I got back to our cottage and lost our keys. Thank you so much to the night shift security guard and the on call maintenance man for helping us out. You guys really saved us and will definitely be staying here again---> Cottage was beautiful "
The price is Rp2.490.292
Rp2.928.583 total
includes taxes & fees
29 Jun - 30 Jun
The Cottages at Golden Village Palms RV Resort
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
View from room

The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

3.0 star property
9.8 out of 10, Exceptional, (20)
"The motel was clean and tidy, nothing fancy, in good condition. The owner was great too! I would definitely stay there again!"
The price is Rp1.982.923
Rp2.347.781 total
includes taxes & fees
26 Jun - 27 Jun
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
Wilderness Lakes RV Resort
Individually furnished, bed sheets

Wilderness Lakes RV Resort

2.0 star property
8.8 out of 10, Excellent, (70)
"Cute cabin but a bit small. "
Wilderness Lakes RV Resort
Coral Tree House
Outdoor pool

Coral Tree House

3.0 star property
10.0 out of 10, Exceptional, (19)
"Michelle and Greg were great host they very kind and generous. Very knowledgeable about the surrounding area. Absolutely lovely place to stay."
Coral Tree House
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

Frequently asked questions

Are there holiday rentals 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. Winchester is known for its wineries and coffee shops. Make sure you have time to check out the bars while you're in the area.

How many holiday rentals will I find in Winchester?

Choose from 31 Expedia holiday rentals in Winchester for a memorable holiday.

What can I see and do in Winchester?

Explore the area and family-friendly sights such as Orange Empire Railroad Museum, or get out into nature at a spot like Diamond Valley Lake Marina. Pechanga Resort & Casino and Soboba Casino 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 like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.