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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Winchester

1 Bed Room Casita-Suite with Private Entrance
Outdoor dining

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 ￥7,705
￥19,546 total
includes taxes & fees
Sep 28 - Sep 29
1 Bed Room Casita-Suite with Private Entrance
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!
Pool

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
Exterior

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
Outdoor pool

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
Terrace/patio

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
The Motorist Choice: Queen Bed and Hot Shower, Smoking & Non-smoking Room | 1 bedroom, individually decorated, individually furnished, desk

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 ￥17,039
￥20,174 total
includes taxes & fees
Sep 26 - Sep 27
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
Amazing Views Villa with Spa / Close to Winery
Outdoor dining

Amazing Views Villa with Spa / Close to Winery

The price is ￥60,978
￥160,404 total
includes taxes & fees
Sep 28 - Sep 29
Amazing Views Villa with Spa / Close to Winery
Villa with indoor pool in Temecula wine country-VRBO
Fridge, microwave, oven, stovetop

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 ￥66,277
￥165,241 total
includes taxes & fees
Sep 30 - Oct 1
Villa with indoor pool in Temecula wine country-VRBO
The Cottages at Golden Village Palms RV Resort
3 outdoor pools, pool umbrellas, sun loungers

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 ￥22,289
￥26,211 total
includes taxes & fees
Sep 28 - Sep 29
The Cottages at Golden Village Palms RV Resort
Adults 21+, Bring your peace or your party - more seclusion with less intrusion
Property grounds

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 ￥2,657
￥5,901 total
includes taxes & fees
Sep 26 - Sep 27
Adults 21+, Bring your peace or your party - more seclusion with less intrusion
Beautiful Villa located in Temecula Wine Country
Outdoor pool

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
Property grounds

Secluded mystical cabin in Idyllwild-Pine Cove

9.6 out of 10, Exceptional, (4)
"Lots of wildlife, very rustic cabin experience "
The price is ￥9,299
￥23,322 total
includes taxes & fees
Oct 7 - Oct 8
Secluded mystical cabin in Idyllwild-Pine Cove
Pet friendly cabin-Fully fenced yard! Pets stay free!
Property grounds

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

10.0 out of 10, Exceptional, (192)
"Enjoyed three nights here. The cabin is very cute and comfortable. Jay is a great host and there to answer any questions. The fenced backyard was perfect for our pup."
Pet friendly cabin-Fully fenced yard! Pets stay free!
The Little Cabin 🌲The coziest cabin on the Mountain.
Property grounds

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 ￥13,949
￥29,145 total
includes taxes & fees
Sep 28 - Sep 29
The Little Cabin 🌲The coziest cabin on the Mountain.
5BR/4Bth Entire Grand Estate near Winery Fallbrook
Pool

5BR/4Bth Entire Grand Estate near Winery Fallbrook

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 ￥20,060
￥60,338 total
includes taxes & fees
Sep 29 - Sep 30
5BR/4Bth Entire Grand Estate near Winery Fallbrook
Clear your mind in the country /minutes 2 the city
Outdoor pool

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 ￥14,023
￥16,975 total
includes taxes & fees
Sep 29 - Sep 30
Clear your mind in the country /minutes 2 the city
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!
Property grounds

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
Dining

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!!
Property grounds

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 ￥14,613
￥24,946 total
includes taxes & fees
Sep 28 - Sep 29
Cactus Garden Cottage…Best Location!!
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
Exterior

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 ￥17,138
￥35,284 total
includes taxes & fees
Sep 29 - Sep 30
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.
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Top Winchester Hotel Reviews

Signature Temecula

Signature Temecula

10/10 Excellent
"Staff made us feel welcome. They provided items we had forgotten. Rooms were clean. It was our second stay."
Penny 1-night trip
Posted 1 day ago
Signature Temecula

Find out more about Winchester

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Winchester?

Yes, you can find vacation rentals near well known sights in Winchester, or you can choose a secluded option if you're looking for relaxation. Winchester is known for its wineries and coffeehouses. Make sure you have time to check out the bars while you're in the area.

What's the top vacation rental in Winchester?

Paradise Vacation Estate - Largest Luxury Private Vacation Resort: This vacation home rental near Winchester offers an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and an arcade game room so you can immerse yourself in your vacation.

How many vacation rentals will I find in Winchester?

Choose from 32 Expedia vacation rentals in Winchester for a memorable vacation.

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 larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private properties you can stay in for a short or long stay in Winchester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.