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Winchester Holiday Rentals

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Holiday Rentals in Winchester

1 Bed Room Casita-Suite with Private Entrance
9.8 out of 10, Exceptional, (55)
"Super comfortable and neat space to stay for 3 days! My host was extremely hospitable and answered my questions nearly as quickly as I wrote them!! Highly recommend I would stay again!!!"
United States
Lynette
The price is AU$172
includes taxes & fees
21 Oct - 22 Oct
1 Bed Room Casita-Suite with Private Entrance
•Charming One-Level Home • Feels Like Home
The price is AU$877
includes taxes & fees
20 Oct - 21 Oct
•Charming One-Level Home • Feels Like Home
3RV/ parking/Netflix/ private/excellent location
8.4 out of 10, Very good, (7)
"Very clean Owners were very sweet and helpful. "
United States
erika
The price is AU$194
includes taxes & fees
20 Oct - 21 Oct
3RV/ parking/Netflix/ private/excellent location
The Pony Experience Farm Stay! 501c3
8.4 out of 10, Very good, (5)
"Me and my daughter couldn’t have asked for a better experience. Hosts were attentive to us and the animals were AMAZING to be around. Horses, peacocks, dogs, fowl, all very welcoming and happy to have guests around. I just wish…nothing. It was great. Very serene too."
United States
Megan
The price is AU$490
includes taxes & fees
3 Nov - 4 Nov
The Pony Experience Farm Stay! 501c3
Sunrise Vista - Glamping Sunsets Over Mt. Palomar
The price is AU$267
includes taxes & fees
20 Oct - 21 Oct
Sunrise Vista - Glamping Sunsets Over Mt. Palomar
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."
United States
Jesus
The price is AU$366
includes taxes & fees
20 Oct - 21 Oct
Coral Tree House
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3.0 star property
9.8 out of 10, Exceptional, (22)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is AU$210
includes taxes & fees
20 Oct - 21 Oct
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
Secluded mystical cabin in Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (4)
"Lots of wildlife, very rustic cabin experience "
United States
Robert H.
The price is AU$246
includes taxes & fees
28 Oct - 29 Oct
Secluded mystical cabin in Idyllwild-Pine Cove
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
10.0 out of 10, Exceptional, (38)
"just a quick one night stay- it was great"
United States
Rick M.
The price is AU$358
includes taxes & fees
22 Oct - 23 Oct
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
9.6 out of 10, Exceptional, (25)
"We stayed there the whole trip. Never even went into town. The property has great amenities and we brought our food and cooked easily. Traeger gril is a definite plus! Would book it again."
United States
david W.
The price is AU$481
includes taxes & fees
11 Nov - 12 Nov
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Cactus Garden Cottage…Best Location!!
10.0 out of 10, Exceptional, (50)
"A sweet and perfect cottage! We had looked into overpriced hotels in Temecula for a wedding but ultimately decided to stay here and so glad we did! It's very private and charming and the host thought of all the touches to make our stay great."
United States
Kelly
The price is AU$265
includes taxes & fees
22 Oct - 23 Oct
Cactus Garden Cottage…Best Location!!
The Cottages at Golden Village Palms RV Resort
3.0 star property
9.2 out of 10, Wonderful, (73)
"This is a hidden jem in Hemet love the pools the grounds are well maintained and I will definitely be staying here again"
United States
mary
The price is AU$273
includes taxes & fees
21 Oct - 22 Oct
The Cottages at Golden Village Palms RV Resort
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
The price is AU$439
includes taxes & fees
20 Oct - 21 Oct
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Dog Friendly A-frame Hot Tub Nature Views
2.0 star property
The price is AU$503
includes taxes & fees
13 Nov - 14 Nov
Dog Friendly A-frame Hot Tub Nature Views
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler
9.8 out of 10, Exceptional, (8)
"Property was spacious for two, listing was very accurate. Clean and comfortable casita with an accommodative owner. Would recommend to anyone looking for a place to stay."
United States
Jacob W.
The price is AU$205
includes taxes & fees
20 Oct - 21 Oct
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler
Moonrise Cottage at Buena Terra Lavender Farm
10.0 out of 10, Exceptional, (7)
"The pictures online don't do this gorgeous and charming cottage justice. Absolutely lovely! Our host was really kind and thoughtful. Beautifully landscaped. Quiet and peaceful. We love this hidden gem!!! Thank you Heidi for making our stay wonderful"
United States
Lisa R.
The price is AU$503
includes taxes & fees
20 Oct - 21 Oct
Moonrise Cottage at Buena Terra Lavender Farm
Dog-friendly mountain home with hot tub & amazing views - near town & hiking
8.4 out of 10, Very good, (131)
"Enjoyed our stay "
United States
Cody
The price is AU$426
includes taxes & fees
26 Oct - 27 Oct
Dog-friendly mountain home with hot tub & amazing views - near town & hiking
Twin Rock Tree House - Vintage Cabin
9.8 out of 10, Exceptional, (27)
"We enjoyed our weekend stay at Twin Rocks. It’s a lovely place, very clean and such nice touches. I enjoyed sitting outside in the front and on the back porch, and all the light coming in from the many windows."
United States
Eve R.
The price is AU$356
includes taxes & fees
20 Oct - 21 Oct
Twin Rock Tree House - Vintage Cabin
Wildland Zen Den: Tiny House Retreat with Fireplace, Grill, AC, Hammock, Record
10.0 out of 10, Exceptional, (6)
"It was the perfect escape from fireworks as my dog gets very anxious. It was very relaxing to be there."
United States
Brianna J.
The price is AU$399
includes taxes & fees
22 Oct - 23 Oct
Wildland Zen Den: Tiny House Retreat with Fireplace, Grill, AC, Hammock, Record
TheTiny Beach House at Coral Tree House
10.0 out of 10, Exceptional, (4)
"Amazing loved everything the property Can't wait to go back"
United States
Daniel D.
The price is AU$445
includes taxes & fees
20 Oct - 21 Oct
TheTiny Beach House at 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.
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Top Winchester Hotel Reviews

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$172 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!: This highly rated holiday home rental in Winchester is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 33 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.