Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

Coral Tree House

Coral Tree House
3.0 star property
Fallbrook
10.0 out of 10, Exceptional, (22 reviews)
"Michelle is very friendly and responsive. The room is beautiful. We really enjoyed our stay "
United States
Huaming
The price is S$301
includes taxes & fees
15 Feb - 16 Feb
Coral Tree House

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 reviews)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is S$181
includes taxes & fees
14 Feb - 15 Feb
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
10.0 out of 10, Exceptional, (1 review)
"I happened to receive a complimentary upgrade during my visit, and it added a special touch to my stay. The cabin itself was wonderful and Cayla at Idyllwild Realty was great! The cabin was a perfect getaway and walking distance to town."
United States
Heather
The price is S$168
includes taxes & fees
18 Feb - 19 Feb
Idyllwild Realty Vacations

The Cottages at Golden Village Palms RV Resort

The Cottages at Golden Village Palms RV Resort
3.0 star property
Hemet
9.2 out of 10, Wonderful, (83 reviews)
"Amazing stay, will visit again"
United States
Miguel
The price is S$224
includes taxes & fees
15 Feb - 16 Feb
The Cottages at Golden Village Palms RV Resort

Family Getaway w/ Pool, 8 Mi to Lake Elsinore!

Family Getaway w/ Pool, 8 Mi to Lake Elsinore!
3.0 star property
Wildomar
The price is S$425
includes taxes & fees
16 Feb - 17 Feb
Family Getaway w/ Pool, 8 Mi to Lake Elsinore!

Hike, Sip & Explore: Couples Retreat in Fallbrook

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
Fallbrook
The price is S$335
includes taxes & fees
18 Feb - 19 Feb
Hike, Sip & Explore: Couples Retreat in Fallbrook
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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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.

What are some of the best holiday rentals that Winchester has to offer?

Idyllwild Realty Vacations: This holiday home rental outside of Winchester comes with free WiFi so that you can feel at home during your trip. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Winchester?

Choose from 32 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 Lake Perris. 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.