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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (91 reviews)
"Adorable stay"
United States
Alexandra
$115 nightly
The price is $125
Oct 12 - Oct 13
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, (10 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
Oct 11 - Oct 12
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
Oct 7 - Oct 8
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 living room with a sofa, a coffee table, a dining area with chairs, and a large window with blinds.

5. 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.
$347 nightly
The price is $347
Nov 6 - Nov 7
Total with taxes and fees
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
A pool surrounded by various potted plants and rocks.

6. 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.
$227 nightly
The price is $243
Oct 12 - Oct 13
Total with taxes and fees
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
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
$77 nightly
The price is $85
Oct 7 - Oct 8
Total with taxes and fees
1 King Bed | Non-Smoking
A hotel room with a bed, a nightstand, a vase of flowers, and a clock.

8. 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 7 - Oct 8
Total with taxes and fees
Harry's Man Cave: The New Star Motel Experience
Exterior

9. 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
$146 nightly
The price is $161
Oct 14 - Oct 15
Total with taxes and fees
Idyllwild Realty Vacations
Two white wicker chairs with yellow cushions in an outdoor setting with hanging plants and a pergola.

10. 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.
$394 nightly
The price is $394
Oct 12 - Oct 13
Total with taxes and fees
Romantic, private and surrounded by best Wineries!
Two red Adirondack chairs facing each other with a wooden cabin in the background.

11. Tranquil Studio at Eagle Creek

Tranquil Studio at Eagle Creek
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (1 review)
"We had a fabulous time in Idyllwild! The small-town vibe, the kindness of the locals, and the spectacular hikes did not disappoint. Our host, Heather, went above and beyond by upgrading us to a larger property because she thought the cabin we originally booked would be too tight for four people. We truly felt like VIPs in the main house. Everything was top-notch, beautifully kept, and felt incredibly homey. Check-in and check-out were completely seamless thanks to the keypad system. This was...
United States
Delphine
$237 nightly
The price is $237
Oct 12 - Oct 13
Total with taxes and fees
Tranquil Studio at Eagle Creek
A wooden cabin with a staircase, a covered porch, and a garden with various plants.

12. 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
Oct 7 - Oct 8
Total with taxes and fees
Cozy cabin retreat nestled among forest trees
A long dining table set for a meal with candles, placed on a terrace with a city view at night.

13. 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.
$726 nightly
The price is $726
Oct 7 - Oct 8
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.

14. 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.
$1,091 nightly
The price is $1,207
Oct 7 - Oct 8
Total with taxes and fees
Hilltop Wine Estate- Pickleball | Pool | 360 views
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.

15. 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.
$506 nightly
The price is $559
Oct 20 - Oct 21
Total with taxes and fees
Temecula Wine Country Stone Creek Ranch
A rustic cabin with a wooden deck, surrounded by tall trees.

16. 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
Oct 7 - Oct 8
Total with taxes and fees
Dog-friendly mountain home with amazing views - near town & hiking
A hot tub with water jets, a clock, string lights, and a view of mountains.

17. PRIVATE - Hilltop Estate W/ Views, Pool, Hot Tub, Mini Golf & More!!

PRIVATE - Hilltop Estate W/ Views, Pool, Hot Tub, Mini Golf & More!!
Murrieta
9.8 out of 10, Exceptional, (13 reviews)
"A great stay with family, lots of space, great place to relax"
United States
Andrew
$830 nightly
The price is $926
Oct 7 - Oct 8
Total with taxes and fees
PRIVATE - Hilltop Estate W/ Views, Pool, Hot Tub, Mini Golf & More!!
A bedroom with a bed, a dining table with chairs, a large window, and a black accent wall.

18. Loft: Serene Mountain Retreat w Fireplace Pets Ok

Loft: Serene Mountain Retreat w Fireplace Pets Ok
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (15 reviews)
"The property exceeded my expectations! Great location."
United States
Stephanie H.
$215 nightly
The price is $235
Oct 7 - Oct 8
Total with taxes and fees
Loft: Serene Mountain Retreat w Fireplace Pets Ok
A rustic outdoor setting with a large metal structure labeled "BLOOMER TRAILERS," a fire pit, and a dining area with wicker furniture.

19. 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
$315 nightly
The price is $315
Oct 7 - Oct 8
Total with taxes and fees
The Pony Experience Farm Stay! 501c3
A snow-covered triangular cabin with a porch and a green door.

20. Idyllwild Cabin: HotTub, Fireplace&Mountain Views!

Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (39 reviews)
"Very relaxing location. BBQ was excellent. Host was helpful."
United States
Christopher F.
$337 nightly
The price is $367
Oct 27 - Oct 28
Total with taxes and fees
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
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

Comfort Inn & Suites Murrieta Temecula Wine Country

Comfort Inn & Suites Murrieta Temecula Wine Country

10/10 Excellent
"The staff was great and accommodations were perfect"
Rochelle 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Murrieta Temecula Wine Country

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.