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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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 AU$181
includes taxes & fees
13 Oct - 14 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 AU$275
includes taxes & fees
13 Oct - 14 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, (110 reviews)
"This place is great!"
United States
Amanda
The price is AU$254
includes taxes & fees
13 Oct - 14 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 AU$585
includes taxes & fees
15 Oct - 16 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 AU$381
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 AU$121
includes taxes & fees
13 Oct - 14 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 AU$558
includes taxes & fees
13 Oct - 14 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 AU$196
includes taxes & fees
13 Oct - 14 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 AU$202
includes taxes & fees
14 Oct - 15 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
9.8 out of 10, Exceptional, (10 reviews)
"Particularly loved the location and the communication with the attentive host."
United States
Aaron R.
The price is AU$793
includes taxes & fees
13 Oct - 14 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 AU$709
includes taxes & fees
13 Oct - 14 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 AU$841
includes taxes & fees
10 Nov - 11 Nov
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 AU$558
includes taxes & fees
14 Oct - 15 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 AU$340
includes taxes & fees
13 Oct - 14 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 AU$126
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 AU$1,814
includes taxes & fees
13 Oct - 14 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 AU$479
includes taxes & fees
13 Oct - 14 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 AU$620
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 Chandelier Château Salt Pool & XL Hot Tub

Kimberly's Chandelier Château Salt Pool & XL 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 AU$786
includes taxes & fees
13 Oct - 14 Oct
Kimberly's Chandelier Château Salt Pool & XL 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 AU$129
includes taxes & fees
13 Oct - 14 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

Comfort Inn & Suites Murrieta Temecula Wine Country

Comfort Inn & Suites Murrieta Temecula Wine Country

10/10 Excellent
"This was an awesome stay. We were there for our friends wedding and the room was decently nice and exceeded our expectations. It was roomy and had tons of space, the bathroom was a good size and it just didn’t feel squished. Our favorite part (that we took most advantage of) was the breakfast. This was super awesome as they had a really good selection of eggs, bacon, bread, even tortillas and ground taco meat! Oh and a waffle maker and coffee. We recommend it and would definitely stay here again if we’re ever in the area."
Clark 2-night trip
Posted 1 hour ago
Comfort Inn & Suites Murrieta Temecula Wine Country

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$181 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.