Lodging Image

Winchester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchester vacation rentals

3 outdoor pools, pool umbrellas, sun loungers

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, (104 reviews)
"This place is great!"
United States
Amanda
The price is AED 555
AED 652 total
includes taxes & fees
11 Aug - 12 Aug
The Cottages at Golden Village Palms RV Resort
The Marylin Monroe: 1 Queen Bed, 1 Sofa Bed, Non-Smoking, CORP RATE | Desk, laptop workspace, blackout drapes, WiFi (free)

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 AED 422
AED 503 total
includes taxes & fees
11 Aug - 12 Aug
Harry's Man Cave: The New Star Motel Experience
Outdoor spa tub

3. Coral Tree House

Coral Tree House
3.0 star property
Fallbrook
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful stay. Beautiful space, great hospitality and perfect tiny home. We thoroughly enjoyed our stay."
United States
Zachary
The price is AED 845
AED 1,152 total
includes taxes & fees
21 Aug - 22 Aug
Coral Tree House
Copper mine | Exterior

4. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.6 out of 10, Exceptional, (10 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 AED 536
AED 590 total
includes taxes & fees
12 Aug - 13 Aug
Idyllwild Realty Vacations
Sleeping Beauty | Desk, iron/ironing board, WiFi (free), bed sheets

5. 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 AED 966
AED 1,774 total
includes taxes & fees
11 Aug - 12 Aug
Always Inn Idyllwild Vacation Cottages
House | 2 bedrooms, high-speed internet

6. 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 AED 528
AED 1,226 total
includes taxes & fees
2 Sep - 3 Sep
Dog Friendly A-frame Hot Tub Nature Views
House (1 Bedroom) | Interior

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

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
Fallbrook
The price is AED 485
AED 985 total
includes taxes & fees
11 Aug - 12 Aug
Hike, Sip & Explore: Couples Retreat in Fallbrook
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Home2 Suites by Hilton Temecula

Home2 Suites by Hilton Temecula

10/10 Excellent
"Close to Old Town Temecula."
Flavia 2-night trip
Posted 1 hour ago
Home2 Suites by Hilton Temecula

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 comes with WiFi so you can feel at home during your trip. 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.