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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (95 reviews)
"Adorable stay"
United States
Alexandra
The price is ￥7,053
￥19,513 total
includes taxes & fees
Nov 1 - Nov 2
1 Bed Room Casita-Suite with Private Entrance
Living area

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, (11 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 ￥26,335
￥29,815 total
includes taxes & fees
Oct 25 - Oct 26
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, (113 reviews)
"Staff was very friendly , very clean , beautiful place"
United States
Albert
The price is ￥23,666
￥27,831 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥30,052
￥66,589 total
includes taxes & fees
Nov 5 - Nov 6
Western Horizon Home
A modern hotel room with a bed, a desk, a chair, and a small bedside table.

5. 1 King Bed | Mobil Acc RI Shwr Suite Nsmk

1 King Bed | Mobil Acc RI Shwr Suite Nsmk
Eastside
10.0 out of 10, Exceptional, (54 reviews)
"Solid spot for a short trip."
United States
Anonymous traveler
The price is ￥11,942
￥13,136 total
includes taxes & fees
Nov 1 - Nov 2
1 King Bed | Mobil Acc RI Shwr Suite Nsmk
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 ￥26,644
￥60,968 total
includes taxes & fees
Nov 18 - Nov 19
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
A building with a flat facade, a blue door, and a sign indicating 'Parking Only'.

7. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Lake Elsinore
10.0 out of 10, Exceptional, (3 reviews)
"This is a decent spot with dependable WiFi and parking close by."
United States
Anonymous traveler
The price is ￥12,682
￥13,950 total
includes taxes & fees
Oct 25 - Oct 26
1 King Bed | Non-Smoking
A pool surrounded by various potted plants and rocks.

8. 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, (19 reviews)
"Very nice house! Everything was very comfortable and wonderful location"
United States
Tina S.
The price is ￥21,495
￥38,468 total
includes taxes & fees
Oct 25 - Oct 26
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
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! Home was clean, comfortable, and the decor was amazing!"
United States
Dana O.
The price is ￥35,123
￥62,551 total
includes taxes & fees
Oct 26 - Oct 27
Romantic, private and surrounded by best Wineries!
Exterior

10. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.8 out of 10, Exceptional, (19 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 ￥22,419
￥24,661 total
includes taxes & fees
Nov 4 - Nov 5
Idyllwild Realty Vacations
A swimming pool with a pink flamingo float, a covered seating area, and a modern outdoor structure.

11. Romantic Villa • Pool • Surrounded by Wineries

Romantic Villa • Pool • Surrounded by Wineries
Valle De Los Caballos
10.0 out of 10, Exceptional, (11 reviews)
"Particularly loved the location and the communication with the attentive host."
United States
Aaron R.
The price is ￥47,019
￥89,023 total
includes taxes & fees
Oct 30 - Oct 31
Romantic Villa • Pool • Surrounded by Wineries
A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

12. 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 ￥18,024
￥21,446 total
includes taxes & fees
Oct 24 - Oct 25
Harry's Man Cave: The New Star Motel Experience
A hotel room with a bed, a TV, a desk, and a chair.

13. 1 King Bed | Mob Acc Tub Ste Nsmk Micfridg

1 King Bed | Mob Acc Tub Ste Nsmk Micfridg
Eastside
10.0 out of 10, Exceptional, (47 reviews)
"Good wifi, decent pool, comfy beds."
United States
Anonymous traveler
The price is ￥11,942
￥13,136 total
includes taxes & fees
Nov 1 - Nov 2
1 King Bed | Mob Acc Tub Ste Nsmk Micfridg
A modern bathroom with a black sink, white toilet, and a glass-enclosed shower area.

14. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Eastside
10.0 out of 10, Exceptional, (56 reviews)
"Bathtub felt more relaxing than expected compared to other motels I've tried."
United States
Anonymous traveler
The price is ￥13,918
￥15,311 total
includes taxes & fees
Oct 25 - Oct 26
2 Queen Beds | Non-Smoking, Micfridge
A kitchenette with a refrigerator, microwave, and a flat-screen TV mounted on the wall.

15. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Eastside
10.0 out of 10, Exceptional, (53 reviews)
"Quiet room, comfortable bed. Loved the easy parking and calm vibe late at night."
United States
Anonymous traveler
The price is ￥11,942
￥13,136 total
includes taxes & fees
Nov 1 - Nov 2
1 King Bed | Non-Smoking, Micfridge
A rustic outdoor seating area with white plastic chairs and a wooden pergola structure.

16. Temecula Wine Country Stone Creek Ranch

Temecula Wine Country Stone Creek Ranch
Temecula
9.2 out of 10, Wonderful, (67 reviews)
"We enjoyed our stay. We loved the trails and beautiful views on the property. The house is very comfortable. It is located very close to all our favorite wineries and restaurants."
United States
Carole H.
The price is ￥45,844
￥87,550 total
includes taxes & fees
Oct 29 - Oct 30
Temecula Wine Country Stone Creek Ranch
A long dining table set for a meal with candles, placed on a terrace with a city view at night.

17. Private European Vineyard w/ Secluded Hilltop Views in Wine Country

Private European Vineyard w/ Secluded Hilltop Views in Wine Country
GlenOak Hills
9.8 out of 10, Exceptional, (18 reviews)
"House is beautiful and the view is amazing. Looking forward to staying there again. Host is great too!"
United States
Joel A.
The price is ￥62,723
￥152,216 total
includes taxes & fees
Nov 2 - Nov 3
Private European Vineyard w/ Secluded Hilltop Views in Wine Country
A pool with large rocks, lounge chairs, and mountains in the background.

18. Hilltop Wine Estate- Pickleball - Pool - 360 views

Hilltop Wine Estate- Pickleball - Pool - 360 views
Temecula
10.0 out of 10, Exceptional, (10 reviews)
"We chose to have a relaxed vacation. Pool, pickleball, made good food, lots of family games, a puzzle and some good tv. This house surpassed our expectations. We did not need to leave the property to have a great time with a big group!"
United States
Rebecca S.
The price is ￥70,227
￥218,192 total
includes taxes & fees
Oct 25 - Oct 26
Hilltop Wine Estate- Pickleball - Pool - 360 views
A wooden cabin with a balcony, surrounded by trees.

19. Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town

Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Everything was clean and the place was really close to town. "
United States
Jack B.
The price is ￥21,942
￥41,455 total
includes taxes & fees
Oct 25 - Oct 26
Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town
A cabin-style lodging with a covered porch, surrounded by a forested area.

20. Quaint Studio in Idyllwild

Quaint Studio in Idyllwild
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay!! Communicative host, beautiful property. Would absolutely stay here again."
United States
Kaylee M.
The price is ￥21,159
￥37,145 total
includes taxes & fees
Nov 3 - Nov 4
Quaint Studio in Idyllwild
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

Hilton Garden Inn Temecula, CA

Hilton Garden Inn Temecula, CA

10/10 Excellent
"The rooms were clean as well as the hotel itself. The staff was very friendly. The only thing I will say is the pillows were flat but since the bed had 3 pillows I was able to sleep comfortable. I will definitely return again."
Yvette 2-night trip
Posted 8 hours ago
Hilton Garden Inn Temecula, CA

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:

  • View our selection of featured holiday rentals in Winchester
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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 35 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.