An aerial view of a densely populated urban area with a river, surrounding mountains, and a clear sky.

Winchester Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winchester vacation 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, (89 reviews)
"Adorable stay"
United States
Alexandra
$113 nightly
The price is $123
Oct 1 - Oct 2
Total with taxes and fees
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, (9 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.
$189 nightly
The price is $189
Sep 30 - Oct 1
Total with taxes and fees
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
$159 nightly
The price is $178
Sep 30 - Oct 1
Total with taxes and fees
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.
$417 nightly
The price is $417
Oct 8 - Oct 9
Total with taxes and fees
Western Horizon Home
A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

5. 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
$121 nightly
The price is $137
Sep 30 - Oct 1
Total with taxes and fees
Harry's Man Cave: The New Star Motel Experience
A living room with a sofa, a coffee table, a dining area with chairs, and a large window with blinds.

6. SALE! Peaceful, Clean, 4x Queen Bed, Spacious!

SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
Hemet
9.4 out of 10, Exceptional, (3 reviews)
"Great affordable option for a quick overnight stay. Super close to Soboba, which was really convenient. Just be sure to bring your own towels and toiletries, as those aren’t provided."
United States
Kiana H.
$340 nightly
The price is $340
Oct 4 - Oct 5
Total with taxes and fees
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
Exterior

7. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.8 out of 10, Exceptional, (16 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
$128 nightly
The price is $141
Oct 6 - Oct 7
Total with taxes and fees
Idyllwild Realty Vacations
A hotel room with two beds, a desk, and a chair.

8. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Lake Elsinore
$82 nightly
The price is $90
Sep 30 - Oct 1
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
Two white wicker chairs with yellow cushions in an outdoor setting with hanging plants and a pergola.

9. 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! Great location! Such a peaceful and relaxing stay! We loved everything about our time in Temecula"
United States
Deborah G.
$372 nightly
The price is $372
Sep 30 - Oct 1
Total with taxes and fees
Romantic, private and surrounded by best Wineries!
A pool surrounded by various potted plants and rocks.

10. 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, (18 reviews)
"Very nice house! Everything was very comfortable and wonderful location"
United States
Tina S.
$221 nightly
The price is $237
Oct 5 - Oct 6
Total with taxes and fees
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
A rustic cabin with a wooden deck, surrounded by tall trees.

11. Dog-friendly mountain home with amazing views - near town & hiking

Dog-friendly mountain home with amazing views - near town & hiking
Idyllwild
8.4 out of 10, Very good, (145 reviews)
"Hot tub was out of order."
United States
debra
$291 nightly
The price is $317
Sep 30 - Oct 1
Total with taxes and fees
Dog-friendly mountain home with amazing views - near town & hiking
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)
"Host was very responsive and the property was beautiful and as described. Had a great time and would stay here again"
United States
Fred S.
$503 nightly
The price is $556
Oct 4 - Oct 5
Total with taxes and fees
Temecula Wine Country Stone Creek Ranch
A rustic outdoor setting with a large metal structure labeled "BLOOMER TRAILERS," a fire pit, and a dining area with wicker furniture.

13. The Pony Experience Farm Stay! 501c3

The Pony Experience Farm Stay! 501c3
Valle De Los Caballos
9.0 out of 10, Wonderful, (7 reviews)
"Great experience at Namaste Farms! The camper was cozy and we loved being able to walk around and visit all the animals. Location is a farm but very close to multiple vineyards and town so it was a perfect getaway."
United States
Jennifer
$299 nightly
The price is $299
Sep 30 - Oct 1
Total with taxes and fees
The Pony Experience Farm Stay! 501c3
An outdoor event with a decorated cake, floral arrangements, and a large 'XVANOS' sign.

14. 4-bedroom house in wonderful Perris with WiFi, AC

4-bedroom house in wonderful Perris with WiFi, AC
Perris
9.4 out of 10, Exceptional, (6 reviews)
"Nice Home and great stay"
United States
Anonymous traveler
$543 nightly
The price is $543
Sep 30 - Oct 1
Total with taxes and fees
4-bedroom house in wonderful Perris with WiFi, AC
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

15. Casa M’Valle 5min to Lake Perris, hospitals w/Rv prkn

Casa M’Valle 5min to Lake Perris, hospitals w/Rv prkn
Moreno Valley
9.4 out of 10, Exceptional, (19 reviews)
"Another great stay here will always come back when in town "
United States
Monique
$541 nightly
The price is $541
Sep 30 - Oct 1
Total with taxes and fees
Casa M’Valle 5min to Lake Perris, hospitals w/Rv prkn
A wooden cabin with a staircase, a covered porch, and a garden with various plants.

16. 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
$311 nightly
The price is $339
Sep 30 - Oct 1
Total with taxes and fees
Cozy cabin retreat nestled among forest trees
A lodge with multiple cabins surrounded by tall pine trees.

17. Relaxing Studio in Idyllwild

Relaxing Studio in Idyllwild
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful spot, as advertised, at a great spot. Could not have asked for better"
United States
Jeff H.
$237 nightly
The price is $237
Oct 1 - Oct 2
Total with taxes and fees
Relaxing Studio in Idyllwild
A hotel room with a bed, a desk, a chair, a TV, and a trash bin.

18. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Lake Elsinore
$78 nightly
The price is $86
Sep 30 - Oct 1
Total with taxes and fees
1 King Bed | Non-Smoking
A rustic wooden cabin with a stone-paved entrance, a porch with a bench, and potted plants.

19. Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3

Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
Valle De Los Caballos
9.8 out of 10, Exceptional, (9 reviews)
"We had an amazing time! The animals were adorable and it was clean, quite and peaceful!! Will definitely be staying again"
United States
Chloe D.
$306 nightly
The price is $329
Oct 5 - Oct 6
Total with taxes and fees
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

20. Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi

Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi
Lake Elsinore
9.8 out of 10, Exceptional, (7 reviews)
"Great location. Quiet neighborhood "
United States
Deb W.
$587 nightly
The price is $639
Oct 6 - Oct 7
Total with taxes and fees
Spacious 4-bedroom house in fabulous Lake Elsinore with AC, WiFi
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

Pala Casino Spa And Resort

Pala Casino Spa And Resort

10/10 Excellent
"Great place and incredible staff. The food was also very good."
David 3-night trip
Posted 3 hours ago
Pala Casino Spa And Resort

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 35 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.