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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winchester vacation rentals

A swimming pool with a curved edge, surrounded by palm trees and a covered patio area with outdoor furniture.

1. 1 Bed Room Casita-Suite with Private Entrance

1 Bed Room Casita-Suite with Private Entrance
Winchester
9.8 out of 10, Exceptional, (89 reviews)
"Adorable stay"
United States
Alexandra
The price is ￥6,794
￥19,269 total
includes taxes & fees
Oct 1 - Oct 2
1 Bed Room Casita-Suite with Private Entrance

2. Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga

Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga
Winchester
10.0 out of 10, Exceptional, (9 reviews)
"The room was exactly what we needed while traveling through with our family for a tournament in Temecula. Plenty of room and everything we needed!"
United States
Vanna S.
The price is ￥26,187
￥29,333 total
includes taxes & fees
Sep 28 - Sep 29
Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga
A resort with multiple swimming pools, palm trees, and a mountainous backdrop.

3. 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, (108 reviews)
"This place is great!"
United States
Amanda
The price is ￥23,749
￥27,929 total
includes taxes & fees
Sep 28 - Sep 29
The Cottages at Golden Village Palms RV Resort
A golf course with a large building and parking lot in the background.

4. Western Horizon Home

Western Horizon Home
Hemet
8.8 out of 10, Excellent, (24 reviews)
"Great place to stay. Great host. Quiet neighborhood. Close to shopping centers."
United States
Taman D.
The price is ￥29,883
￥61,968 total
includes taxes & fees
Oct 8 - Oct 9
Western Horizon Home
A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

5. Harry's Man Cave: The New Star Motel Experience

Harry's Man Cave: The New Star Motel Experience
3.0 star property
Edgemont
9.8 out of 10, Exceptional, (25 reviews)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is ￥18,087
￥21,521 total
includes taxes & fees
Sep 28 - Sep 29
Harry's Man Cave: The New Star Motel Experience
A living room with a sofa, a coffee table, a dining area with chairs, and a large window with blinds.

6. SALE! Peaceful, Clean, 4x Queen Bed, Spacious!

SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
Hemet
9.4 out of 10, Exceptional, (3 reviews)
"Great affordable option for a quick overnight stay. Super close to Soboba, which was really convenient. Just be sure to bring your own towels and toiletries, as those aren’t provided."
United States
Kiana H.
The price is ￥19,817
￥50,487 total
includes taxes & fees
Oct 4 - Oct 5
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!

7. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.8 out of 10, Exceptional, (16 reviews)
"We stayed here for one night and absolutely loved it. the cabin is new, it is beautifully decorated and has all the essentials. The area is quiet and peaceful"
United States
Rocio
The price is ￥21,208
￥23,329 total
includes taxes & fees
Sep 30 - Oct 1
Idyllwild Realty Vacations
A hotel room with two beds, a desk, and a chair.

8. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Lake Elsinore
The price is ￥12,948
￥14,243 total
includes taxes & fees
Sep 28 - Sep 29
1 King Bed | Non-Smoking, Micfridge
Two white wicker chairs with yellow cushions in an outdoor setting with hanging plants and a pergola.

9. Romantic, private and surrounded by best Wineries!

Romantic, private and surrounded by best Wineries!
GlenOak Hills
10.0 out of 10, Exceptional, (31 reviews)
"We loved our stay! Great location! Such a peaceful and relaxing stay! We loved everything about our time in Temecula"
United States
Deborah G.
The price is ￥35,246
￥58,523 total
includes taxes & fees
Sep 28 - Sep 29
Romantic, private and surrounded by best Wineries!
A pool surrounded by various potted plants and rocks.

10. The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!

The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
Valle De Los Caballos
9.6 out of 10, Exceptional, (18 reviews)
"Very nice house! Everything was very comfortable and wonderful location"
United States
Tina S.
The price is ￥21,374
￥37,308 total
includes taxes & fees
Oct 5 - Oct 6
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
A rustic cabin with a wooden deck, surrounded by tall trees.

11. Dog-friendly mountain home with amazing views - near town & hiking

Dog-friendly mountain home with amazing views - near town & hiking
Idyllwild
8.4 out of 10, Very good, (145 reviews)
"Hot tub was out of order."
United States
debra
The price is ￥17,883
￥47,818 total
includes taxes & fees
Sep 28 - Sep 29
Dog-friendly mountain home with amazing views - near town & hiking
A dirt pathway flanked by decorative vases with pampas grass, leading to a gathering area with tables and chairs, surrounded by trees and string lights.

12. Temecula Wine Country Stone Creek Ranch

Temecula Wine Country Stone Creek Ranch
Temecula
9.2 out of 10, Wonderful, (66 reviews)
"Host was very responsive and the property was beautiful and as described. Had a great time and would stay here again"
United States
Fred S.
The price is ￥46,004
￥82,509 total
includes taxes & fees
Sep 28 - Sep 29
Temecula Wine Country Stone Creek Ranch
A rustic outdoor setting with a large metal structure labeled "BLOOMER TRAILERS," a fire pit, and a dining area with wicker furniture.

13. The Pony Experience Farm Stay! 501c3

The Pony Experience Farm Stay! 501c3
Valle De Los Caballos
9.0 out of 10, Wonderful, (7 reviews)
"Great experience at Namaste Farms! The camper was cozy and we loved being able to walk around and visit all the animals. Location is a farm but very close to multiple vineyards and town so it was a perfect getaway."
United States
Jennifer
The price is ￥39,163
￥47,027 total
includes taxes & fees
Sep 28 - Sep 29
The Pony Experience Farm Stay! 501c3
An outdoor event with a decorated cake, floral arrangements, and a large 'XVANOS' sign.

14. 4-bedroom house in wonderful Perris with WiFi, AC

4-bedroom house in wonderful Perris with WiFi, AC
Perris
9.4 out of 10, Exceptional, (6 reviews)
"Nice Home and great stay"
United States
Anonymous traveler
The price is ￥27,603
￥80,449 total
includes taxes & fees
Sep 28 - Sep 29
4-bedroom house in wonderful Perris with WiFi, AC
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

15. Casa M’Valle 5min to Lake Perris, hospitals w/Rv prkn

Casa M’Valle 5min to Lake Perris, hospitals w/Rv prkn
Moreno Valley
9.4 out of 10, Exceptional, (19 reviews)
"Another great stay here will always come back when in town "
United States
Monique
The price is ￥38,534
￥80,370 total
includes taxes & fees
Sep 28 - Sep 29
Casa M’Valle 5min to Lake Perris, hospitals w/Rv prkn
A wooden cabin with a staircase, a covered porch, and a garden with various plants.

16. Cozy cabin retreat nestled among forest trees

Cozy cabin retreat nestled among forest trees
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (16 reviews)
"We absolutely loved our stay at this clean, cozy cabin. The hosts really went above and beyond to make sure the home is well stocked and comfortable, We are already looking forward to visiting again. "
United States
KIM
The price is ￥27,524
￥52,453 total
includes taxes & fees
Sep 28 - Sep 29
Cozy cabin retreat nestled among forest trees
A lodge with multiple cabins surrounded by tall pine trees.

17. Relaxing Studio in Idyllwild

Relaxing Studio in Idyllwild
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful spot, as advertised, at a great spot. Could not have asked for better"
United States
Jeff H.
The price is ￥21,233
￥36,175 total
includes taxes & fees
Oct 1 - Oct 2
Relaxing Studio in Idyllwild
A hotel room with a bed, a desk, a chair, a TV, and a trash bin.

18. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Lake Elsinore
The price is ￥12,324
￥13,557 total
includes taxes & fees
Sep 28 - Sep 29
1 King Bed | Non-Smoking
A rustic wooden cabin with a stone-paved entrance, a porch with a bench, and potted plants.

19. Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3

Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
Valle De Los Caballos
9.8 out of 10, Exceptional, (9 reviews)
"We had an amazing time! The animals were adorable and it was clean, quite and peaceful!! Will definitely be staying again"
United States
Chloe D.
The price is ￥39,320
￥51,666 total
includes taxes & fees
Sep 28 - Sep 29
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

20. Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi

Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi
Lake Elsinore
9.8 out of 10, Exceptional, (7 reviews)
"Great location. Quiet neighborhood "
United States
Deb W.
The price is ￥42,466
￥95,312 total
includes taxes & fees
Oct 4 - Oct 5
Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi
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

Soboba Casino Resort

Soboba Casino Resort

8/10 Good
"Clean room"
Maria Theresa 1-night trip
Posted 1 hour ago
Soboba Casino Resort

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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Look no further and take a look at our great range of rental properties in Winchester!

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?

Idyllwild Realty Vacations: Located near Winchester, this vacation home rental offers a fireplace, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Other favorite homes for rent in Winchester are 1 Bed Room Casita-Suite with Private Entrance and Windridge Manor - Wine Country Retreat w/ 6 Beds, Garden, Pool, Games & BBQ.

How many vacation rentals will I find in Winchester?

Choose from 36 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. K1 Circuit and Pechanga Resort & Casino 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.