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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winchester holiday 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, (87 reviews)
"Adorable stay"
United States
Alexandra
The price is HK$339
HK$961 total
includes taxes & fees
1 Sept - 2 Sept
1 Bed Room Casita-Suite with Private Entrance
A grey stucco exterior with a white door, a small black lantern, and a young tree.

2. Beautiful, brand new next gen suite near Temecula wine country

Beautiful, brand new next gen suite near Temecula wine country
Winchester
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay at this property. Very clean, great space for couples and a quick Uber to all wineries and downtown!"
United States
Mike M.
The price is HK$1,254
HK$1,858 total
includes taxes & fees
1 Sept - 2 Sept
Beautiful, brand new next gen suite near Temecula wine country

3. 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, (8 reviews)
"We needed a place to stay for just one night for an event. This place was just right , well equipped, clean and the neighborhood was great. The host Cheri was so professional and attentive. I would definitely stay again in the future.This place is s private suite attached to a home but it felt very secluded and we had our own backyard and private entrance. The distance to the wineries is perfect , Maybe a 15 minute drive ."
United States
Susana C.
The price is HK$1,450
HK$1,662 total
includes taxes & fees
10 Sept - 11 Sept
Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga
A resort with multiple swimming pools, palm trees, and a mountainous backdrop.

4. 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, (105 reviews)
"This place is great!"
United States
Amanda
The price is HK$1,184
HK$1,392 total
includes taxes & fees
1 Sept - 2 Sept
The Cottages at Golden Village Palms RV Resort
A modern house with a well-lit exterior, a visible air conditioning unit, and a landscaped front yard.

5. Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property

Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property
Menifee
10.0 out of 10, Exceptional, (10 reviews)
"The host was very welcoming. "
United States
Linda L.
The price is HK$776
HK$1,090 total
includes taxes & fees
7 Sept - 8 Sept
Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property
A golf course with a large building and parking lot in the background.

6. Western Horizon Home

Western Horizon Home
Hemet
8.8 out of 10, Excellent, (24 reviews)
"Host was fantastic, house was clean, price was good and would definitely stay here again when in the area. "
United States
Justin p.
The price is HK$1,378
HK$2,789 total
includes taxes & fees
7 Sept - 8 Sept
Western Horizon Home
A living room with a sofa, a coffee table, a dining area with chairs, and a large window with blinds.

7. 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 HK$988
HK$2,689 total
includes taxes & fees
7 Sept - 8 Sept
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
A rustic cabin with a wooden exterior, surrounded by trees and a garden with raised beds and a compost bin.

8. Secluded mystical cabin in Idyllwild-Pine Cove

Secluded mystical cabin in Idyllwild-Pine Cove
Idyllwild-Pine Cove
8.8 out of 10, Excellent, (33 reviews)
"it was a quirky and lovely mountain paradise"
United States
Anonymous traveller
The price is HK$494
HK$1,239 total
includes taxes & fees
1 Sept - 2 Sept
Secluded mystical cabin in Idyllwild-Pine Cove

9. Idyllwild Realty Vacations

Idyllwild Realty Vacations
4.0 star property
Idyllwild
9.8 out of 10, Exceptional, (12 reviews)
"The property was very clean and has almost everything we need. good location and good communication We had a great time."
United States
Jina
The price is HK$1,137
HK$1,250 total
includes taxes & fees
1 Sept - 2 Sept
Idyllwild Realty Vacations
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, (16 reviews)
"Very nice house! Everything was very comfortable and wonderful location"
United States
Tina S.
The price is HK$1,065
HK$1,930 total
includes taxes & fees
1 Sept - 2 Sept
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.

11. 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 HK$1,757
HK$3,129 total
includes taxes & fees
1 Sept - 2 Sept
Romantic, private and surrounded by best 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, (24 reviews)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is HK$902
HK$1,073 total
includes taxes & fees
1 Sept - 2 Sept
Harry's Man Cave: The New Star Motel Experience
A reception desk with a dark wood finish, a glass partition, and a poster on the wall.

13. 1 Queen Bed|Smoking,Micfridge

1 Queen Bed|Smoking,Micfridge
Moreno Valley
The price is HK$700
HK$791 total
includes taxes & fees
7 Sept - 8 Sept
1 Queen Bed|Smoking,Micfridge
A flat-screen TV displaying a 'Watch Free+ Scenery' interface with a serene indoor garden view.

14. Entire cozy two floor guest house located in rainbow near Temecula

Entire cozy two floor guest house located in rainbow near Temecula
Fallbrook
10.0 out of 10, Exceptional, (3 reviews)
"Nice place cozy place definitely recommend!"
United States
Jayden B.
The price is HK$941
HK$1,435 total
includes taxes & fees
1 Sept - 2 Sept
Entire cozy two floor guest house located in rainbow near Temecula
A wooden deck with a stone wall, a rope barrier, and a view of a sunset over a hilly landscape.

15. 2Bedroom 2bath in-law unit with kitchen and washer

2Bedroom 2bath in-law unit with kitchen and washer
Temecula
9.4 out of 10, Exceptional, (6 reviews)
"Beautiful place. The host was really nice and the house was very clean. I will stay here again the next time I’m in the area. "
United States
Byron F.
The price is HK$868
HK$1,370 total
includes taxes & fees
1 Sept - 2 Sept
2Bedroom 2bath in-law unit with kitchen and washer
A window view of a forested area with a clear sky.

16. Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.

Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (33 reviews)
"We enjoyed our 4 night stay at the Lighthouse. We especially loved the location at the ridge line close to hiking and the great views out every window!"
United States
Kim H.
The price is HK$1,051
HK$2,235 total
includes taxes & fees
7 Sept - 8 Sept
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
A landscaped garden with various cacti and succulents, a small pathway, and a metal fence in the background.

17. Cactus Garden Cottage…Best Location!!

Cactus Garden Cottage…Best Location!!
Fallbrook
10.0 out of 10, Exceptional, (73 reviews)
"Loved the location and garden"
United States
Cyrus
The price is HK$776
HK$1,434 total
includes taxes & fees
7 Sept - 8 Sept
Cactus Garden Cottage…Best Location!!
A snow-covered triangular cabin with a porch and a green door.

18. Idyllwild Cabin: HotTub, Fireplace&Mountain Views!

Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (38 reviews)
"We had a great time! Listing is accurate, everything as expected, and the hot tub and views were fantastic! "
United States
Meagan K.
The price is HK$1,043
HK$2,660 total
includes taxes & fees
29 Sept - 30 Sept
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
A cozy log cabin interior with a fireplace, wooden walls, and a comfortable seating area.

19. 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, (144 reviews)
"Hot tub was out of order."
United States
debra
The price is HK$891
HK$2,517 total
includes taxes & fees
1 Sept - 2 Sept
Dog-friendly mountain home with amazing views - near town & hiking
A hammock and two chairs set up in a forested area with string lights.

20. Loft: Serene Mountain Retreat w Fireplace Pets Ok

Loft: Serene Mountain Retreat w Fireplace Pets Ok
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (15 reviews)
"The property exceeded my expectations! Great location."
United States
Stephanie H.
The price is HK$800
HK$1,950 total
includes taxes & fees
1 Sept - 2 Sept
Loft: Serene Mountain Retreat w Fireplace Pets Ok
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

Tahquitz Pines Retreat

Tahquitz Pines Retreat

10/10 Excellent
"It’s our second time staying here and it was peaceful and relaxing as always. The office staff is wonderful and so friendly. We can’t wait to come back!"
Marisol 1-night trip
Posted 6 hours ago
Tahquitz Pines Retreat

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
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

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

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?

Idyllwild Realty Vacations: This holiday home rental outside of Winchester offers a fireplace, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite 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 holiday rentals will I find in Winchester?

Choose from 38 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. K1 Circuit and Pechanga Resort & 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.