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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester vacation 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, (106 reviews)
"This place is great!"
United States
Amanda
The price is ￥23,277
￥27,374 total
includes taxes & fees
Sep 20 - Sep 21
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, (24 reviews)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is ￥17,727
￥21,094 total
includes taxes & fees
Sep 10 - Sep 11
Harry's Man Cave: The New Star Motel Experience

3. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.8 out of 10, Exceptional, (13 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 ￥21,233
￥23,356 total
includes taxes & fees
Sep 22 - Sep 23
Idyllwild Realty Vacations
A snow-covered triangular cabin with a balcony and a door.

4. 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 ￥23,520
￥54,266 total
includes taxes & fees
Sep 9 - Sep 10
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.

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

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
Fallbrook
The price is ￥20,348
￥41,323 total
includes taxes & fees
Oct 8 - Oct 9
Hike, Sip & Explore: Couples Retreat in Fallbrook
A rustic cabin with a porch, surrounded by trees and a gravel driveway.

6. 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 ￥41,081
￥75,491 total
includes taxes & fees
Sep 9 - Sep 10
Always Inn Idyllwild Vacation Cottages
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
"We had a wonderful time at Tahquitz Pines Retreat! The staff at both the front desk and the restaurant were very friendly and welcoming. The check-in and check-out process was quick and smooth, and we also received three complimentary drink coupons to use at the restaurant, which was a nice surprise. The food at the restaurant was really delicious and reasonably priced, which made our dining experience even better. Our cabin was beautiful, cozy, and very comfortable. The property has so many great amenities for both kids and dogs, and our son and our dog both had an amazing time exploring and enjoying everything there. We spent quite a bit of time at the pool and in the recreation room, and we also loved all the beautiful green spaces and little trails throughout the property. It was such a relaxing and family-friendly getaway—the perfect place to slow down and enjoy some peaceful time together. We really enjoyed our stay and would definitely love to come back!"
Cuiyan 1-night trip
Posted less than an hour 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:

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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 38 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.