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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (93 reviews)
"Adorable stay"
United States
Alexandra
The price is HK$353
HK$977 total
includes taxes & fees
18 Oct - 19 Oct
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 HK$1,452
HK$1,664 total
includes taxes & fees
25 Oct - 26 Oct
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, (112 reviews)
"This place is great!"
United States
Amanda
The price is HK$1,185
HK$1,394 total
includes taxes & fees
19 Oct - 20 Oct
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 HK$1,491
HK$3,273 total
includes taxes & fees
17 Oct - 18 Oct
Western Horizon Home
A pool surrounded by various potted plants and rocks.

5. 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 HK$1,185
HK$2,081 total
includes taxes & fees
1 Nov - 2 Nov
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
A hotel room with a bed, a desk, a chair, a TV, and a trash bin.

6. 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 traveller
The price is HK$603
HK$664 total
includes taxes & fees
20 Oct - 21 Oct
1 King Bed | Non-Smoking
Two white wicker chairs with yellow cushions in an outdoor setting with hanging plants and a pergola.

7. 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 HK$1,759
HK$3,132 total
includes taxes & fees
26 Oct - 27 Oct
Romantic, private and surrounded by best Wineries!
A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

8. 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 HK$903
HK$1,074 total
includes taxes & fees
16 Oct - 17 Oct
Harry's Man Cave: The New Star Motel Experience
Exterior

9. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.8 out of 10, Exceptional, (18 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 HK$1,169
HK$1,286 total
includes taxes & fees
26 Oct - 27 Oct
Idyllwild Realty Vacations
A swimming pool with a pink flamingo float, a covered seating area, and a modern outdoor structure.

10. 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 HK$2,354
HK$4,411 total
includes taxes & fees
16 Oct - 17 Oct
Romantic Villa • Pool • Surrounded by Wineries
A living room with two grey sofas, a coffee table, and a patterned rug.

11. BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY

BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY
Moreno Valley
10.0 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay , host was great and location also very calm and beautiful, recommend 10/10"
United States
Christy M.
The price is HK$1,766
HK$3,967 total
includes taxes & fees
19 Oct - 20 Oct
BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY
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)
"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 HK$2,296
HK$4,384 total
includes taxes & fees
20 Oct - 21 Oct
Temecula Wine Country Stone Creek Ranch
A snow-covered triangular cabin with a balcony and a door.

13. Dog Friendly A-frame Hot Tub Nature Views

Dog Friendly A-frame Hot Tub Nature Views
2.0 star property
Idyllwild
10.0 out of 10, Exceptional, (2 reviews)
"The place was great. Very comfortable and well outfitted. It's in a neighborhood, down a short dirt road, no driveway, you will need to park on the street and leave room for neighbor to get to their driveway gate. There are stairs down to the door (not wheelchair accessible). Not a big deal, just a note if you're bringing a lot of stuff or more than 1 car it will be tight."
United States
Anthony
The price is HK$1,535
HK$3,042 total
includes taxes & fees
22 Oct - 23 Oct
Dog Friendly A-frame Hot Tub Nature Views
Two red Adirondack chairs facing each other with a wooden cabin in the background.

14. Tranquil Studio at Eagle Creek

Tranquil Studio at Eagle Creek
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (1 review)
"We had a fabulous time in Idyllwild! The small-town vibe, the kindness of the locals, and the spectacular hikes did not disappoint. Our host, Heather, went above and beyond by upgrading us to a larger property because she thought the cabin we originally booked would be too tight for four people. We truly felt like VIPs in the main house. Everything was top-notch, beautifully kept, and felt incredibly homey. Check-in and check-out were completely seamless thanks to the keypad system. This was...
United States
Delphine
The price is HK$1,059
HK$1,876 total
includes taxes & fees
29 Oct - 30 Oct
Tranquil Studio at Eagle Creek
A hotel room with two beds, a desk, and a chair.

15. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Lake Elsinore
10.0 out of 10, Exceptional, (3 reviews)
"Appreciated that the TV remote actually had batteries included. Free WiFi stayed strong enough for work calls and streaming shows late into the night without issues. Kitchenette with fridge and microwave let us prep simple snacks anytime we wanted too."
United States
Anonymous traveller
The price is HK$626
HK$689 total
includes taxes & fees
1 Nov - 2 Nov
1 King Bed | Non-Smoking, Micfridge
A pool with large rocks, lounge chairs, and mountains in the background.

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

Hilltop Wine Estate- Pickleball - Pool - 360 views
Temecula
10.0 out of 10, Exceptional, (9 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 HK$3,665
HK$11,036 total
includes taxes & fees
18 Oct - 19 Oct
Hilltop Wine Estate- Pickleball - Pool - 360 views
A wooden cabin with a staircase, a covered porch, and a garden with various plants.

17. 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 HK$1,295
HK$2,649 total
includes taxes & fees
22 Oct - 23 Oct
Cozy cabin retreat nestled among forest trees
A hot tub with a view of a mountainous landscape.

18. Relaxing Wine Country Stay - Hot Tub - Agave Farm

Relaxing Wine Country Stay - Hot Tub - Agave Farm
Valle De Los Caballos
10.0 out of 10, Exceptional, (17 reviews)
"The casita was very nice - clean, comfortable with a great view. Wish we could have stayed there longer."
United States
Shelley E.
The price is HK$2,747
HK$3,469 total
includes taxes & fees
20 Oct - 21 Oct
Relaxing Wine Country Stay - Hot Tub - Agave Farm
A swimming pool with a waterfall feature, surrounded by tropical plants and a wooden fence.

19. Kimberly's Private Palm Château Salt Pool & Hot Tub

Kimberly's Private Palm Château Salt Pool & Hot Tub
Lake Elsinore
10.0 out of 10, Exceptional, (52 reviews)
"Wonderful stay! Sunshine, skydiving, hot tub and pool."
United States
Dean G.
The price is HK$2,433
HK$4,725 total
includes taxes & fees
28 Oct - 29 Oct
Kimberly's Private Palm Château Salt Pool & Hot Tub
A hotel room with two beds, a desk, a chair, a television, and a small bathroom.

20. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Lake Elsinore
10.0 out of 10, Exceptional, (3 reviews)
"Room felt cozy but included all essentials from TV to queen bed and AC working effectively to keep cool during warmer nights here near Lake Elsinore area"
United States
Anonymous traveller
The price is HK$641
HK$705 total
includes taxes & fees
21 Oct - 22 Oct
2 Queen Beds | Non-Smoking
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

Pala Casino Spa And Resort

Pala Casino Spa And Resort

10/10 Excellent
"The room was very large and beautifully decorated."
Bridget 1-night trip
Posted 9 hours ago
Pala Casino Spa And 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:

  • 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 35 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.