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Featured Holiday Homes in Winchester

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

Winchester
With a stay at this vacation home in Winchester, you'll be in the mountains, within a 15-minute drive of Wilson Creek Winery and Paint a Dream.
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!
Blue Lagoon Oasis - Pool - Firepit - Close to Wineries

Blue Lagoon Oasis - Pool - Firepit - Close to Wineries

Murrieta
With a stay at this vacation home, you'll be centrally located in Murrieta, within a 15-minute drive of Pechanga Resort & Casino and Old Town Temecula Community ...
Blue Lagoon Oasis - Pool - Firepit - Close to Wineries
Wolf's Creek: Hot tub, On the Creek!

Wolf's Creek: Hot tub, On the Creek!

Idyllwild
With a stay at this vacation home in Idyllwild, you'll be in the mountains, just steps from San Jacinto Mountains and a 5-minute drive from Idyllwild Park.
Wolf's Creek: Hot tub, On the Creek!
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20% Off Mar - Amazing Pool, Spa,Volleyball,Views!

20% Off Mar - Amazing Pool, Spa,Volleyball,Views!

Murrieta
When you stay at this vacation home in Murrieta, you'll be 11 minutes by car from Santa Rosa Plateau Ecological Reserve.
20% Off Mar - Amazing Pool, Spa,Volleyball,Views!
❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️

❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️

Temecula
The price is AU$578 per night from 28 Apr to 29 Apr
AU$578
includes taxes & fees
28 Apr - 29 Apr
When you stay at this vacation home in Temecula, you'll be in the mountains, within a 15-minute drive of Pechanga Resort & Casino and Wilson Creek Winery.
❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️
1/Bed Room Casita-Suite with Private Entrance

1/Bed Room Casita-Suite with Private Entrance

Winchester
The price is AU$212 per night from 23 Apr to 24 Apr
AU$212
includes taxes & fees
23 Apr - 24 Apr
With a stay at this vacation home in Winchester, you'll be within a 15-minute drive of Wilson Creek Winery and Wiens Cellars.
1/Bed Room Casita-Suite with Private Entrance
20% Off Mar Dates - LRG Kitchen,Pool,Spa,Wineries!

20% Off Mar Dates - LRG Kitchen,Pool,Spa,Wineries!

Temecula
With a stay at this vacation home in Temecula, you'll be within a 15-minute drive of Wilson Creek Winery and Old Town Temecula Community Theater.
20% Off Mar Dates - LRG Kitchen,Pool,Spa,Wineries!
Quarter Horse by AvantStay | Countryside Retreat

Quarter Horse by AvantStay | Countryside Retreat

Temecula
Located in Temecula, this vacation home is in a rural location, within a 15-minute drive of California Watercolors and Fallbrook Pioneer Odd Fellows ...
Quarter Horse by AvantStay | Countryside Retreat
Wine Country Resort  -  Close to Wineries

Wine Country Resort - Close to Wineries

Winchester
Located in Winchester, this vacation home is within a 15-minute drive of Wilson Creek Winery and Old Town Temecula Community Theater.
Wine Country Resort - Close to Wineries
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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.

Winchester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winchester vacation homes are the perfect way for you to wing it.

Holiday houses in Winchester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winchester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winchester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winchester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winchester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winchester Holiday Homes essential information

Accommodation
752 Holiday Homes
Lowest Price
AU$113
Highest Price
AU$578
Popular accommodation
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!, Blue Lagoon Oasis - Pool - Firepit - Close to Wineries, Wolf's Creek: Hot tub, On the Creek!, 20% Off Mar - Amazing Pool, Spa,Volleyball,Views!, ❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️, 1/Bed Room Casita-Suite with Private Entrance, 20% Off Mar Dates - LRG Kitchen,Pool,Spa,Wineries!, Quarter Horse by AvantStay | Countryside Retreat, Wine Country Resort - Close to Wineries

Top trending hotels in Winchester

Pala Casino Spa And Resort

Pala Casino Spa And Resort

4 out of 5
11154 Highway 76, Pala, CA
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 7 May to 8 May
AU$208
includes taxes & fees
7 May - 8 May
When you stay at Pala Casino Spa And Resort in Pala, you'll be in the mountains, within a 15-minute drive of Pechanga Resort & Casino and Harrah's Resort Southern ...
Pala Casino Spa And Resort
Hotel Xola

Hotel Xola

2.5 out of 5
24630 Sunnymead Boulevard, Moreno Valley, CA
The price is AU$113 per night from 19 May to 20 May
AU$113
includes taxes & fees
19 May - 20 May
With a stay at Hotel Xola in Moreno Valley, you'll be within a 15-minute drive of University of California, Riverside and Riverside Convention Center.
Hotel Xola
Signature Temecula

Signature Temecula

3 out of 5
28980 Old Town Front St., Temecula, CA
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 28 Apr to 29 Apr
AU$122
includes taxes & fees
28 Apr - 29 Apr
Located in Temecula, Signature Temecula is within a 5-minute drive of Old Town Temecula Community Theater and Temecula Creek Inn Golf Course.
Signature Temecula
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Soboba Casino Resort

Soboba Casino Resort

3.5 out of 5
22777 Soboba Road, San Jacinto, CA
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 30 Apr to 1 May
AU$203
includes taxes & fees
30 Apr - 1 May
Located in San Jacinto, Soboba Casino Resort is just steps from San Jacinto Mountains and 15 minutes by foot from Soboba Springs Country Club.
Soboba Casino Resort
Don't see what you're looking for?
See all available properties in Winchester
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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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^Subject to availability and chosen travel dates.