Winchester Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winchester holiday rentals

A resort with multiple swimming pools, palm trees, and a mountainous backdrop.

1. 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 NZ$316
includes taxes & fees
6 Dec - 7 Dec
The Cottages at Golden Village Palms RV Resort
A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

2. 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 NZ$245
includes taxes & fees
6 Nov - 7 Nov
Harry's Man Cave: The New Star Motel Experience
Exterior

3. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
10.0 out of 10, Exceptional, (21 reviews)
"The cabin was lovely and bigger than expected for the price we paid. Everything was clean and organized. My favorite thing was the fenced backyard because we had our dog with us and he was able to run around freely. Communication was great and quick with the host."
United States
Angela
The price is NZ$254
includes taxes & fees
6 Dec - 7 Dec
Idyllwild Realty Vacations
A rustic cabin with a porch, surrounded by trees and a gravel driveway.

4. Always Inn Idyllwild Vacation Cottages

Always Inn Idyllwild Vacation Cottages
3.0 star property
Fern Valley
7.0 out of 10, Good, (12 reviews)
"Great property, well kept, great for extended vacations"
United States
Domonick
The price is NZ$847
includes taxes & fees
9 Nov - 10 Nov
Always Inn Idyllwild Vacation Cottages
A snow-covered triangular cabin with a balcony and a door.

5. 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 NZ$620
includes taxes & fees
18 Nov - 19 Nov
Dog Friendly A-frame Hot Tub Nature Views
A living room with a sectional sofa, a coffee table, a purple armchair, and a bookshelf filled with books and decorative items.

6. Hike, Sip & Explore: Couples Retreat in Fallbrook

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
Fallbrook
The price is NZ$479
includes taxes & fees
9 Nov - 10 Nov
Hike, Sip & Explore: Couples Retreat in Fallbrook
A bedroom with a bed, bedside tables, a ceiling fan, a window with curtains, and a door.

7. Pet-friendly Riverside Retreat w/ Private Spa!

Pet-friendly Riverside Retreat w/ Private Spa!
3.0 star property
Canyon Crest
The price is NZ$1,392
includes taxes & fees
24 Nov - 25 Nov
Pet-friendly Riverside Retreat w/ Private Spa!
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

A hotel lobby with a checkered floor, two sofas, a small table, and a refrigerator stocked with beverages.
Hampton Inn And Suites Hemet

Hampton Inn And Suites Hemet

Hampton Inn And Suites Hemet
Hemet

10/10 Excellent

Comfortable and safe place to stay, which had everything I needed.
Australia
Anonymous traveller
Reviewed September 23, 2019
Hampton Inn And Suites Hemet

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 favorite 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 depends 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 NZ$149 per night. Entering your travel dates in the search wizard you might find 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.