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Winchester Vacation Rentals

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Check prices for these dates

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

Our top choices for Winchester vacation rentals

Outdoor pool

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 AED 159
AED 450 total
includes taxes & fees
1 Oct - 2 Oct
1 Bed Room Casita-Suite with Private Entrance
Smart TV

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 AED 612
AED 685 total
includes taxes & fees
29 Sep - 30 Sep
Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga
3 outdoor pools, pool umbrellas, sun loungers

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, (110 reviews)
"This place is great!"
United States
Amanda
The price is AED 555
AED 652 total
includes taxes & fees
29 Sep - 30 Sep
The Cottages at Golden Village Palms RV Resort
Exterior

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 AED 974
AED 1,734 total
includes taxes & fees
10 Oct - 11 Oct
Western Horizon Home
The Marylin Monroe: 1 Queen Bed, 1 Sofa Bed, Non-Smoking, CORP RATE | Desk, laptop workspace, blackout drapes, WiFi (free)

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 AED 422
AED 503 total
includes taxes & fees
29 Sep - 30 Sep
Harry's Man Cave: The New Star Motel Experience
Smart TV

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 AED 463
AED 1,179 total
includes taxes & fees
11 Oct - 12 Oct
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
Copper mine | Exterior

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 AED 495
AED 545 total
includes taxes & fees
30 Sep - 1 Oct
Idyllwild Realty Vacations
WiFi (free)

8. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Lake Elsinore
The price is AED 302
AED 333 total
includes taxes & fees
29 Sep - 30 Sep
1 King Bed | Non-Smoking, Micfridge
Terrace/patio

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 AED 823
AED 1,367 total
includes taxes & fees
29 Sep - 30 Sep
Romantic, private and surrounded by best Wineries!
Outdoor pool

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 AED 499
AED 871 total
includes taxes & fees
5 Oct - 6 Oct
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
Exterior

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 AED 418
AED 1,117 total
includes taxes & fees
29 Sep - 30 Sep
Dog-friendly mountain home with amazing views - near town & hiking
Outdoor banquet area

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 AED 1,074
AED 1,927 total
includes taxes & fees
29 Sep - 30 Sep
Temecula Wine Country Stone Creek Ranch
Property grounds

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 AED 915
AED 1,098 total
includes taxes & fees
29 Sep - 30 Sep
The Pony Experience Farm Stay! 501c3
Outdoor banquet area

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 AED 645
AED 1,879 total
includes taxes & fees
29 Sep - 30 Sep
4-bedroom house in wonderful Perris with WiFi, AC
Private kitchen

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 AED 900
AED 1,877 total
includes taxes & fees
29 Sep - 30 Sep
Casa M’Valle 5min to Lake Perris, hospitals w/Rv prkn
Exterior

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 AED 606
AED 1,185 total
includes taxes & fees
29 Sep - 30 Sep
Cozy cabin retreat nestled among forest trees
Property grounds

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 AED 496
AED 845 total
includes taxes & fees
1 Oct - 2 Oct
Relaxing Studio in Idyllwild
WiFi (free)

18. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Lake Elsinore
The price is AED 288
AED 317 total
includes taxes & fees
29 Sep - 30 Sep
1 King Bed | Non-Smoking
Property grounds

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 AED 918
AED 1,203 total
includes taxes & fees
5 Oct - 6 Oct
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
Coffee/tea maker, fridge, microwave, oven

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 AED 992
AED 2,226 total
includes taxes & fees
5 Oct - 6 Oct
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

Best Western Plus Diamond Valley Inn

Best Western Plus Diamond Valley Inn

10/10 Excellent
"Love the shower head and it was well kept"
Veronica 2-night trip
Posted less than an hour ago
Best Western Plus Diamond Valley Inn

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.