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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (95 reviews)
"Adorable stay"
United States
Alexandra
$115 nightly
The price is $125
Oct 21 - Oct 22
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, (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.
$209 nightly
The price is $209
Oct 25 - Oct 26
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, (113 reviews)
"Staff was very friendly , very clean , beautiful place"
United States
Albert
$159 nightly
The price is $178
Oct 21 - Oct 22
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 29 - Oct 30
Total with taxes and fees
Western Horizon Home
A vending machine with various beverage options and a payment interface.

5. 1 King Bed | Mobil Acc RI Shwr Suite Nsmk

1 King Bed | Mobil Acc RI Shwr Suite Nsmk
Eastside
10.0 out of 10, Exceptional, (54 reviews)
"Solid spot for a short trip."
United States
Anonymous traveler
$76 nightly
The price is $84
Nov 1 - Nov 2
Total with taxes and fees
1 King Bed | Mobil Acc RI Shwr Suite Nsmk
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.
$356 nightly
The price is $356
Nov 8 - Nov 9
Total with taxes and fees
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
A hotel room with a bed, a desk, a chair, a TV, and a trash bin.

7. 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 traveler
$80 nightly
The price is $88
Oct 21 - Oct 22
Total with taxes and fees
1 King Bed | Non-Smoking
A pool surrounded by various potted plants and rocks.

8. 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.
$229 nightly
The price is $245
Nov 1 - Nov 2
Total with taxes and fees
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
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! Home was clean, comfortable, and the decor was amazing!"
United States
Dana O.
$399 nightly
The price is $399
Oct 21 - Oct 22
Total with taxes and fees
Romantic, private and surrounded by best Wineries!
Exterior

10. Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.8 out of 10, Exceptional, (19 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 21 - Oct 22
Total with taxes and fees
Idyllwild Realty Vacations
A swimming pool with a pink flamingo float, a covered seating area, and a modern outdoor structure.

11. Romantic Villa • Pool • Surrounded by Wineries

Romantic Villa • Pool • Surrounded by Wineries
Valle De Los Caballos
10.0 out of 10, Exceptional, (11 reviews)
"Particularly loved the location and the communication with the attentive host."
United States
Aaron R.
$514 nightly
The price is $568
Oct 21 - Oct 22
Total with taxes and fees
Romantic Villa • Pool • Surrounded by Wineries
A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

12. 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
Oct 21 - Oct 22
Total with taxes and fees
Harry's Man Cave: The New Star Motel Experience
A hotel room with a bed, a desk, a television, and a window with curtains.

13. 1 King Bed | Mob Acc Tub Ste Nsmk Micfridg

1 King Bed | Mob Acc Tub Ste Nsmk Micfridg
Eastside
10.0 out of 10, Exceptional, (47 reviews)
"Good wifi, decent pool, comfy beds."
United States
Anonymous traveler
$76 nightly
The price is $84
Nov 1 - Nov 2
Total with taxes and fees
1 King Bed | Mob Acc Tub Ste Nsmk Micfridg
A vending machine with a variety of beverages and snacks.

14. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Eastside
10.0 out of 10, Exceptional, (56 reviews)
"Bathtub felt more relaxing than expected compared to other motels I've tried."
United States
Anonymous traveler
$89 nightly
The price is $98
Oct 21 - Oct 22
Total with taxes and fees
2 Queen Beds | Non-Smoking, Micfridge
A hotel room with a bed, a desk, and a chair.

15. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Eastside
10.0 out of 10, Exceptional, (53 reviews)
"Quiet room, comfortable bed. Loved the easy parking and calm vibe late at night."
United States
Anonymous traveler
$76 nightly
The price is $84
Nov 1 - Nov 2
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
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.

16. 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.
$500 nightly
The price is $553
Oct 25 - Oct 26
Total with taxes and fees
Temecula Wine Country Stone Creek Ranch
A long dining table set for a meal with candles, placed on a terrace with a city view at night.

17. Private European Vineyard w/ Secluded Hilltop Views in Wine Country

Private European Vineyard w/ Secluded Hilltop Views in Wine Country
GlenOak Hills
9.8 out of 10, Exceptional, (18 reviews)
"House is beautiful and the view is amazing. Looking forward to staying there again. Host is great too!"
United States
Joel A.
$990 nightly
The price is $990
Nov 4 - Nov 5
Total with taxes and fees
Private European Vineyard w/ Secluded Hilltop Views in Wine Country
A pool with large rocks, lounge chairs, and mountains in the background.

18. 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.
$1,121 nightly
The price is $1,237
Oct 21 - Oct 22
Total with taxes and fees
Hilltop Wine Estate- Pickleball - Pool - 360 views
A wooden cabin with a balcony, surrounded by trees.

19. Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town

Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Everything was clean and the place was really close to town. "
United States
Jack B.
$243 nightly
The price is $265
Oct 21 - Oct 22
Total with taxes and fees
Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town
A natural outdoor setting with a stream, rocks, and dense greenery.

20. Quaint Studio in Idyllwild

Quaint Studio in Idyllwild
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (3 reviews)
"Great location, well maintained, beautiful property, peaceful, quiet, relaxing, comfortable bed, all the basics necessary for a quick and cozy stay. I would definitely visit again. The location is very convenient to everything in town."
United States
Ana F.
$239 nightly
The price is $239
Oct 26 - Oct 27
Total with taxes and fees
Quaint Studio in Idyllwild
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

Pala Casino Spa And Resort

Pala Casino Spa And Resort

10/10 Excellent
"Todo estuvo muy bien, el personal,el lugar, el ambiente muy tranquilo."
Roger 2-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 $125 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.