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

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester vacation rentals

Outdoor pool

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
Smart TV

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.
$181 nightly
The price is $181
Sep 20 - Sep 21
Total with taxes and fees
Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga
3 outdoor pools, pool umbrellas, sun loungers

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, (107 reviews)
"This place is great!"
United States
Amanda
$159 nightly
The price is $178
Sep 20 - Sep 21
Total with taxes and fees
The Cottages at Golden Village Palms RV Resort
Exterior

4. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
HEMET
$91 nightly
The price is $102
Sep 20 - Sep 21
Total with taxes and fees
1 Queen Bed | Smoking
Exterior

5. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
HEMET
$101 nightly
The price is $113
Sep 20 - Sep 21
Total with taxes and fees
2 Queen Beds | Non-Smoking
Exterior

6. 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.
$420 nightly
The price is $420
Oct 17 - Oct 18
Total with taxes and fees
Western Horizon Home
Outdoor pool

7. 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.
$227 nightly
The price is $243
Sep 21 - Sep 22
Total with taxes and fees
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
Smart TV

8. 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.
$353 nightly
The price is $353
Oct 4 - Oct 5
Total with taxes and fees
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
The Marylin Monroe: 1 Queen Bed, 1 Sofa Bed, Non-Smoking, CORP RATE | Desk, laptop workspace, blackout drapes, WiFi (free)

9. 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 20 - Sep 21
Total with taxes and fees
Harry's Man Cave: The New Star Motel Experience
Exterior

10. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Lake Elsinore
$79 nightly
The price is $87
Sep 20 - Sep 21
Total with taxes and fees
1 King Bed | Non-Smoking
Terrace/patio

11. 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.
$394 nightly
The price is $394
Sep 21 - Sep 22
Total with taxes and fees
Romantic, private and surrounded by best Wineries!
Terrace/patio

12. 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
Sep 20 - Sep 21
Total with taxes and fees
Tranquil Studio at Eagle Creek
Copper mine | Exterior

13. 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
$145 nightly
The price is $159
Sep 20 - Sep 21
Total with taxes and fees
Idyllwild Realty Vacations
Interior

14. Hidden Jackpot Near Soboba Casino

Hidden Jackpot Near Soboba Casino
Hemet
10.0 out of 10, Exceptional, (3 reviews)
"Had the best stay at this home, very clean, very comfortable. Irma was responsive and helpful, and we very much look forward to staying here again! It is the best place to stay in the area, as I have stayed in many different areas. Thank again! "
United States
Tyler S.
$783 nightly
The price is $783
Oct 5 - Oct 6
Total with taxes and fees
Hidden Jackpot Near Soboba Casino
Outdoor banquet area

15. 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 21 - Sep 22
Total with taxes and fees
4-bedroom house in wonderful Perris with WiFi, AC
Outdoor dining

16. 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.
$945 nightly
The price is $945
Sep 21 - Sep 22
Total with taxes and fees
Private European Vineyard w/ Secluded Hilltop Views in Wine Country
Interior

17. Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.

Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (36 reviews)
"We enjoyed our 4 night stay at the Lighthouse. We especially loved the location at the ridge line close to hiking and the great views out every window!"
United States
Kim H.
$259 nightly
The price is $282
Sep 20 - Sep 21
Total with taxes and fees
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Interior

18. Entire cozy two floor guest house located in rainbow near Temecula

Entire cozy two floor guest house located in rainbow near Temecula
Fallbrook
10.0 out of 10, Exceptional, (4 reviews)
"Nice place cozy place definitely recommend!"
United States
Jayden B.
$150 nightly
The price is $150
Sep 20 - Sep 21
Total with taxes and fees
Entire cozy two floor guest house located in rainbow near Temecula
Outdoor banquet area

19. 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.
$480 nightly
The price is $533
Sep 20 - Sep 21
Total with taxes and fees
Temecula Wine Country Stone Creek Ranch
Exterior

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

Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (38 reviews)
"Very relaxing location. BBQ was excellent. Host was helpful."
United States
Christopher F.
$315 nightly
The price is $343
Sep 23 - Sep 24
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

Everhome Suites Temecula Wine Country

Everhome Suites Temecula Wine Country

10/10 Excellent
"property is very clean, staff are very kind and friendly, overall amazing experience"
Bashar 1-night trip
Posted less than an hour ago
Everhome Suites 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 $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: You might like this vacation home rental near Winchester. It 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 Wine Country Resort - Close to Wineries.

How many vacation rentals will I find in Winchester?

Choose from 36 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.