Winchester Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Winchester holiday rentals

Outdoor pool
Coral Tree House

Coral Tree House

Coral Tree House
3.0 star property
Fallbrook
10.0 out of 10, Exceptional, (22)
"Michelle is very friendly and responsive. The room is beautiful. We really enjoyed our stay "
United States
Huaming
The price is S$307
includes taxes & fees
1 Jan - 2 Jan, 2026
Coral Tree House
Individually decorated, individually furnished, desk, laptop workspace
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

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

The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3.0 star property
Moreno Valley
9.8 out of 10, Exceptional, (23)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is S$176
includes taxes & fees
1 Jan - 2 Jan, 2026
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3 outdoor pools, pool umbrellas, pool loungers
The Cottages at Golden Village Palms RV Resort

The Cottages at Golden Village Palms RV Resort

The Cottages at Golden Village Palms RV Resort
3.0 star property
Hemet
9.4 out of 10, Exceptional, (80)
"Amazing stay, will visit again"
United States
Miguel
The price is S$228
includes taxes & fees
31 Dec - 1 Jan, 2026
The Cottages at Golden Village Palms RV Resort
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

Tahquitz Pines Retreat

Tahquitz Pines Retreat

10/10 Excellent
"Cute spot to stay and so close to all the shops"
Andrea 1-night trip
Posted 1 day ago
Tahquitz Pines Retreat

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. K1 Circuit and Pechanga Resort & 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.