Photo by Betsy Wood

Winchester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winchester

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (53)
"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!!!"
The price is AU$204
includes taxes & fees
28 Sept - 29 Sept
1 Bed Room Casita-Suite with Private Entrance

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

10.0 out of 10, Exceptional, (39)
"Enjoyed our time in this lovely home. The beds were comfortable and we really enjoyed the back yard!"
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (48)
"Was everything we hoped for!"
Chateau Vino - French Style Chalet

Paradise Vacation Estate - Largest Luxury Private Vacation Resort

9.6 out of 10, Exceptional, (187)
"Our stay was AWESOME! Our large family was able to be accommodated. We enjoyed playing pickle ball on the tennis courts. The cool nights were warmed by the spa. The hot days we cooled off in the pool, and we walked the gorgeous lit up grounds at night. Thank you for a wonderful time."
Paradise Vacation Estate - Largest Luxury Private Vacation Resort

Luxury Estate with Private Pool, close to Temecula Wine Country and Trails

10.0 out of 10, Exceptional, (3)
"Location is spectacular. Very clean and spacious location with lots of fun and luxurious extras. Host is very accommodating and welcoming. Will be booking again in the future. Booked for a small event and had no regrets! Highly recommend! "
Luxury Estate with Private Pool, close to Temecula Wine Country and Trails

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

3.0 star property
9.8 out of 10, Exceptional, (21)
"Our stay was pleasant, office manger kind and helpful with "
The price is AU$207
includes taxes & fees
30 Sept - 1 Oct
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

Amazing Views Villa with Spa / Close to Winery

The price is AU$1,665
includes taxes & fees
24 Sept - 25 Sept
Amazing Views Villa with Spa / Close to Winery

Villa with indoor pool in Temecula wine country-VRBO

9.2 out of 10, Wonderful, (33)
"Perfect place for our short weekend getaway. Stayed for 3 nights. Home had plenty of room inside and out. GreatCommunication with management. "
The price is AU$1,715
includes taxes & fees
5 Oct - 6 Oct
Villa with indoor pool in Temecula wine country-VRBO

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"
The price is AU$269
includes taxes & fees
5 Oct - 6 Oct
The Cottages at Golden Village Palms RV Resort

Adults 21+, Bring your peace or your party - more seclusion with less intrusion

4.0 out of 10, (1)
"when we checked in, we had a few sites to choose from and but none of them seemed to fit our 10person tent, so we had "
The price is AU$64
includes taxes & fees
29 Sept - 30 Sept
Adults 21+, Bring your peace or your party - more seclusion with less intrusion

Beautiful Villa located in Temecula Wine Country

9.0 out of 10, Wonderful, (23)
"Our stay was great! Visiting for a nearby wedding at local winery. The home was an amazing place to stay with more enough room for everyone to have their own space but able to host together! Can’t wait to spend another stay at this location!"
Beautiful Villa located in Temecula Wine Country

Secluded mystical cabin in Idyllwild-Pine Cove

9.6 out of 10, Exceptional, (4)
"Lots of wildlife, very rustic cabin experience "
The price is AU$253
includes taxes & fees
7 Oct - 8 Oct
Secluded mystical cabin in Idyllwild-Pine Cove

Pet friendly cabin-Fully fenced yard! Pets stay free!

10.0 out of 10, Exceptional, (191)
"Cozy and comfortable. The best spot to bring the dogs. "
Pet friendly cabin-Fully fenced yard! Pets stay free!

The Little Cabin 🌲The coziest cabin on the Mountain.

10.0 out of 10, Exceptional, (92)
"We stayed for the weekend. The hosts were excellent. The cabin was great and close to town. We would definitely stay again. "
The price is AU$322
includes taxes & fees
28 Sept - 29 Sept
The Little Cabin 🌲The coziest cabin on the Mountain.

3-Acre Estate with View, Gated Avenue, 3000 Sq Ft

8.4 out of 10, Very good, (6)
"Had a great experience staying at this property. Huge land and space and very secluded from other neighbors. "
The price is AU$645
includes taxes & fees
29 Sept - 30 Sept
3-Acre Estate with View, Gated Avenue, 3000 Sq Ft

Clear your mind in the country /minutes 2 the city

9.4 out of 10, Exceptional, (28)
"Great place, comfy bed, and great location. "
The price is AU$177
includes taxes & fees
29 Sept - 30 Sept
Clear your mind in the country /minutes 2 the city

5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

9.8 out of 10, Exceptional, (307)
"Magical 100 year old cabin! Ladybug swarms in the afternoons, squirrels, Steller's Jay birds (big blue jays that love peanuts!) Beautiful grounds, tons of room inside and out. Kids loved the private path to creek. "
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

The Creek-Side Cabin: Spa, 5 Star, Upgraded, Big Deck, Quiet, Walk To Town

9.8 out of 10, Exceptional, (140)
"Comfortable and fun log cabin house:) we enjoyed our stay and look forward to returning in the future!"
The Creek-Side Cabin: Spa, 5 Star, Upgraded, Big Deck, Quiet, Walk To Town

Cactus Garden Cottage…Best Location!!

10.0 out of 10, Exceptional, (48)
"Great experience, lovely little cottage. Quiet and secluded, just what we were looking for! "
The price is AU$259
includes taxes & fees
23 Oct - 24 Oct
Cactus Garden Cottage…Best Location!!

IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!

10.0 out of 10, Exceptional, (38)
"The cabin is cozy, quiet and well appointed! It has everything you need for a short or longer visit. "
The price is AU$363
includes taxes & fees
29 Sept - 30 Sept
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
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

Top Winchester Hotel Reviews

Find out more about Winchester

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$64 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?

Paradise Vacation Estate - Largest Luxury Private Vacation Resort: This holiday home rental outside of Winchester offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and an arcade/games room so that you can immerse yourself in your holiday.

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 Diamond Valley Lake Marina. Pechanga Resort & Casino and Menifee Lakes Golf Course 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.