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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Winchester vacation rentals

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, (87 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
Exterior detail

2. Beautiful, brand new next gen suite near Temecula wine country

Beautiful, brand new next gen suite near Temecula wine country
Winchester
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay at this property. Very clean, great space for couples and a quick Uber to all wineries and downtown!"
United States
Mike M.
$223 nightly
The price is $237
Sep 3 - Sep 4
Total with taxes and fees
Beautiful, brand new next gen suite near Temecula wine country
Living area

3. 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, (8 reviews)
"We needed a place to stay for just one night for an event. This place was just right , well equipped, clean and the neighborhood was great. The host Cheri was so professional and attentive. I would definitely stay again in the future.This place is s private suite attached to a home but it felt very secluded and we had our own backyard and private entrance. The distance to the wineries is perfect , Maybe a 15 minute drive ."
United States
Susana C.
$191 nightly
The price is $191
Sep 3 - Sep 4
Total with taxes and fees
Ta-Ta Darling Luxury Temecula Wine Country Retreat Near Lake Skinner & Pechanga
Pool

4. 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, (105 reviews)
"This place is great!"
United States
Amanda
$156 nightly
The price is $174
Sep 9 - Sep 10
Total with taxes and fees
The Cottages at Golden Village Palms RV Resort
Exterior

5. Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property

Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property
Menifee
10.0 out of 10, Exceptional, (10 reviews)
"The host was very welcoming. "
United States
Linda L.
$139 nightly
The price is $139
Sep 7 - Sep 8
Total with taxes and fees
Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property
Exterior

6. Western Horizon Home

Western Horizon Home
Hemet
8.8 out of 10, Excellent, (24 reviews)
"Host was fantastic, house was clean, price was good and would definitely stay here again when in the area. "
United States
Justin p.
$360 nightly
The price is $360
Sep 7 - Sep 8
Total with taxes and fees
Western Horizon Home
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.
$230 nightly
The price is $246
Sep 7 - Sep 8
Total with taxes and fees
The Perfect Getaway! Temecula Wine Country Guest House. Prime Location!
Terrace/patio

8. 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.
$399 nightly
The price is $399
Sep 3 - Sep 4
Total with taxes and fees
Romantic, private and surrounded by best Wineries!
The Marylin Monroe: 1 Queen Bed, 1 Sofa Bed, Non-Smoking, CORP RATE

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, (24 reviews)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
$121 nightly
The price is $137
Sep 3 - Sep 4
Total with taxes and fees
Harry's Man Cave: The New Star Motel Experience
Copper mine | Exterior

10. Idyllwild Realty Vacations

Idyllwild Realty Vacations
4.0 star property
Idyllwild
9.8 out of 10, Exceptional, (12 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
$128 nightly
The price is $140
Sep 9 - Sep 10
Total with taxes and fees
Idyllwild Realty Vacations
Interior

11. 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.
$776 nightly
The price is $776
Sep 8 - Sep 9
Total with taxes and fees
Hidden Jackpot Near Soboba Casino
Interior

12. Family Hemet Home Hot Tub + RV/Boat Parking

Family Hemet Home Hot Tub + RV/Boat Parking
Hemet
9.6 out of 10, Exceptional, (4 reviews)
"It was a Great place to stay. "
United States
FELIPE
$573 nightly
The price is $573
Sep 8 - Sep 9
Total with taxes and fees
Family Hemet Home Hot Tub + RV/Boat Parking
Property grounds

13. Secluded mystical cabin in Idyllwild-Pine Cove

Secluded mystical cabin in Idyllwild-Pine Cove
Idyllwild-Pine Cove
8.8 out of 10, Excellent, (33 reviews)
"it was a quirky and lovely mountain paradise"
United States
Anonymous traveler
$158 nightly
The price is $158
Sep 8 - Sep 9
Total with taxes and fees
Secluded mystical cabin in Idyllwild-Pine Cove
Lobby

14. 1 Queen Bed|Smoking,Micfridge

1 Queen Bed|Smoking,Micfridge
Moreno Valley
$89 nightly
The price is $101
Sep 3 - Sep 4
Total with taxes and fees
1 Queen Bed|Smoking,Micfridge
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
$550 nightly
The price is $550
Sep 3 - Sep 4
Total with taxes and fees
4-bedroom house in wonderful Perris with WiFi, AC
Terrace/patio

16. 2Bedroom 2bath in-law unit with kitchen and washer

2Bedroom 2bath in-law unit with kitchen and washer
Temecula
9.4 out of 10, Exceptional, (6 reviews)
"Beautiful place. The host was really nice and the house was very clean. I will stay here again the next time I’m in the area. "
United States
Byron F.
$181 nightly
The price is $197
Sep 3 - Sep 4
Total with taxes and fees
2Bedroom 2bath in-law unit with kitchen and washer
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, (33 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.
$262 nightly
The price is $285
Sep 7 - Sep 8
Total with taxes and fees
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Exterior

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

Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (38 reviews)
"We had a great time! Listing is accurate, everything as expected, and the hot tub and views were fantastic! "
United States
Meagan K.
$319 nightly
The price is $347
Sep 8 - Sep 9
Total with taxes and fees
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Outdoor banquet area

19. Temecula Wine Country Stone Creek Ranch

Temecula Wine Country Stone Creek Ranch
Temecula
9.2 out of 10, Wonderful, (65 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
Sep 3 - Sep 4
Total with taxes and fees
Temecula Wine Country Stone Creek Ranch
Exterior

20. 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
$321 nightly
The price is $349
Sep 7 - Sep 8
Total with taxes and fees
Cozy cabin retreat nestled among forest trees
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 Mesa Golf Resort

Pala Mesa Golf Resort

8/10 Good
"Everything was great except the water pressure In the shower."
Michael 1-night trip
Posted 4 hours ago
Pala Mesa Golf 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 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.