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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!
10.0 out of 10, Exceptional, (41)
"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!
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!!!"
The price is €98
includes taxes & fees
28 Oct - 29 Oct
1 Bed Room Casita-Suite with Private Entrance
Chateau Vino - French Style Chalet
10.0 out of 10, Exceptional, (50)
"Was everything we hoped for!"
Chateau Vino - French Style Chalet
Pool paradise near Temecula Wine Country w/ spa, pool table, games, pic wall
2.0 star property
10.0 out of 10, Exceptional, (5)
"Had a lovely weekend. House was beautiful and perfect. Hosts were exceptional. "
Pool paradise near Temecula Wine Country w/ spa, pool table, games, pic wall
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 "
The price is €118
includes taxes & fees
16 Oct - 17 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 "
The price is €141
includes taxes & fees
28 Oct - 29 Oct
Secluded mystical cabin in Idyllwild-Pine Cove
Paradise Vacation Estate - Largest Luxury Private Vacation Resort
9.6 out of 10, Exceptional, (188)
"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
9.8 out of 10, Exceptional, (6)
"Would love to give 5star but there were a few hiccups like hot tub and fireplace that make us not want to give 5 - whereas responsiveness was fantastic and Maliha stopped by twice to fix what was wrong so that's a big plus and therefore a 4 and not a 3. "
The price is €789
includes taxes & fees
16 Oct - 17 Oct
Luxury Estate with Private Pool, close to Temecula Wine Country and Trails
Amazing Views Villa with Spa / Close to Winery
10.0 out of 10, Exceptional, (1)
"The bedrooms were spacious and clean. The house was inviting and the outdoor area was massive with amazing views of the valley. The host was responsive and kind. We had a nice stay. "
The price is €958
includes taxes & fees
20 Oct - 21 Oct
Amazing Views Villa with Spa / Close to Winery
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 €153
includes taxes & fees
21 Oct - 22 Oct
The Cottages at Golden Village Palms RV Resort
Clear your mind in the country /minutes 2 the city
9.2 out of 10, Wonderful, (29)
"Great place, comfy bed, and great location. "
The price is €103
includes taxes & fees
19 Oct - 20 Oct
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, (310)
"Home and property in great condition, it was a very peaceful and cozy getaway. Would definitely visit again."
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!
7 BR/5.5 bath PERMITTED TEMECULA WINE COUNTRY VACATION RENTAL
9.8 out of 10, Exceptional, (40)
"This is our 3rd time staying at this house. We had a great time ."
7 BR/5.5 bath PERMITTED TEMECULA WINE COUNTRY VACATION RENTAL
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
Villa with indoor pool in Temecula wine country-VRBO
9.2 out of 10, Wonderful, (35)
"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 €993
includes taxes & fees
19 Oct - 20 Oct
Villa with indoor pool in Temecula wine country-VRBO
The Little Cabin 🌲The coziest cabin on the Mountain.
10.0 out of 10, Exceptional, (96)
"This was my second stay at the Little Cabin. It continues to be a comfortable and well-equipped cabin in a great location."
The Little Cabin 🌲The coziest cabin on the Mountain.
Charming working ranch in the heart of Temecula wine country
10.0 out of 10, Exceptional, (5)
"Fully equipped family friendly house fully in a peaceful area. "
The price is €275
includes taxes & fees
10 Nov - 11 Nov
Charming working ranch in the heart of Temecula wine country
Temecula Wine Country Villa / Save Up to 30% Long Stay
10.0 out of 10, Exceptional, (25)
"Fun and easy stay in a wonderful home. Temecula is a SoCal gem for families who like wine and want to relax. We will be back. "
Temecula Wine Country Villa / Save Up to 30% Long Stay
House with pool/spa/minutes to wineries
8.8 out of 10, Excellent, (33)
"Booked this property for family staying in town for a wedding — it’s very convenient to the wineries (and other "
The price is €921
includes taxes & fees
21 Oct - 22 Oct
House with pool/spa/minutes to wineries
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub
2.0 star property
9.0 out of 10, Wonderful, (12)
"Excellent house and location, great host communication."
The price is €377
includes taxes & fees
26 Oct - 27 Oct
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub
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, apart-hotels, 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 favorite 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 depends 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 €98 per night. Entering your travel dates in the search wizard you might find 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 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 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.