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Featured Holiday Homes in Winchester

Charming Hill Top Wine Country Villa- Minutes to all Vineyards

Charming Hill Top Wine Country Villa- Minutes to all Vineyards

Temecula
With a stay at this vacation home in Temecula, you'll be within a 15-minute drive of Pechanga Resort & Casino and Ponte Winery.
Charming Hill Top Wine Country Villa- Minutes to all Vineyards
Beautiful Ranch Home with views, pool, spa & fire pit.

Beautiful Ranch Home with views, pool, spa & fire pit.

Temecula
When you stay at this vacation home in Temecula, you'll be in the mountains, within a 5-minute drive of Wiens Cellars and Wilson Creek Winery.
Beautiful Ranch Home with views, pool, spa & fire pit.
Private modern barn custom home, mini golf, ping pong.sleeps 16. Best location.

Private modern barn custom home, mini golf, ping pong.sleeps 16. Best location.

Temecula
Located in Temecula, this vacation home is in a rural location, within a 5-minute drive of Rancho Palomar Winery and Avensole Winery.
Private modern barn custom home, mini golf, ping pong.sleeps 16. Best location.
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3-Bedrooms in Idyllwild - AC, 
Jacuzzi, Sauna, Fitness-Game Room,  Epic Views

3-Bedrooms in Idyllwild - AC, Jacuzzi, Sauna, Fitness-Game Room, Epic Views

2 out of 5
Idyllwild
With a stay at this vacation home in Idyllwild, you'll be steps from San Jacinto Mountains and a 4-minute drive from Idyllwild Park.
3-Bedrooms in Idyllwild - AC, Jacuzzi, Sauna, Fitness-Game Room, Epic Views
Beautiful Storybook Home with hot tub, in the forest. Close to hiking trails.

Beautiful Storybook Home with hot tub, in the forest. Close to hiking trails.

Idyllwild-Pine Cove
With a stay at this vacation home in Idyllwild (Fern Valley), you'll be steps from San Jacinto Mountains and 8 minutes by foot from Mount San Jacinto State ...
Beautiful Storybook Home with hot tub, in the forest. Close to hiking trails.
4 Bedroom Home Just Minutes From Wine Country

4 Bedroom Home Just Minutes From Wine Country

Winchester
With a stay at this vacation home in Winchester, you'll be within a 15-minute drive of Wilson Creek Winery and Wiens Cellars.
4 Bedroom Home Just Minutes From Wine Country
Private Wine Country estate with 360 view of Temecula Valley

Private Wine Country estate with 360 view of Temecula Valley

Temecula
Located in Temecula, this vacation home is in a rural location, within a 5-minute drive of Rancho Palomar Winery and Avensole Winery.
Private Wine Country estate with 360 view of Temecula Valley
Sprawling California Ranch House w/ Courtyard!

Sprawling California Ranch House w/ Courtyard!

Temecula
With a stay at this vacation home in Temecula, you'll be within a 15-minute drive of Pechanga Resort & Casino and Galway Downs.
Sprawling California Ranch House w/ Courtyard!
Above the Clouds 17 acre Gated Hilltop Estate with Stunning Views

Above the Clouds 17 acre Gated Hilltop Estate with Stunning Views

2 out of 5
Fallbrook
With a stay at this vacation home in Fallbrook, you'll be 8.4 mi (13.6 km) from Pechanga Resort & Casino and 4.7 mi (7.6 km) from Pala Casino Spa Resort.
Above the Clouds 17 acre Gated Hilltop Estate with Stunning Views
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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
590 Holiday Homes
Lowest Price
AU$116
Highest Price
AU$176
Popular accommodation
Charming Hill Top Wine Country Villa- Minutes to all Vineyards, Beautiful Ranch Home with views, pool, spa & fire pit., Private modern barn custom home, mini golf, ping pong.sleeps 16. Best location. , 3-Bedrooms in Idyllwild - AC, Jacuzzi, Sauna, Fitness-Game Room, Epic Views, Beautiful Storybook Home with hot tub, in the forest. Close to hiking trails., 4 Bedroom Home Just Minutes From Wine Country, Private Wine Country estate with 360 view of Temecula Valley, Sprawling California Ranch House w/ Courtyard!, Above the Clouds 17 acre Gated Hilltop Estate with Stunning Views

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$176 per night from 2 Jan to 3 Jan
AU$176
includes taxes & fees
2 Jan - 3 Jan 2025
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
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$129 per night from 24 Dec to 25 Dec
AU$129
includes taxes & fees
24 Dec - 25 Dec
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
Tahquitz Pines Retreat

Tahquitz Pines Retreat

2 out of 5
55251 S. Circle Dr, Idyllwild, CA
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 2 Jan to 3 Jan
AU$174
includes taxes & fees
2 Jan - 3 Jan 2025
With a stay at Tahquitz Pines Retreat in Idyllwild, you'll be in the mountains, just steps from San Jacinto Mountains and a 2-minute drive from Mount San Jacinto ...
Tahquitz Pines Retreat
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Hotel Xola

Hotel Xola

2.5 out of 5
24630 Sunnymead Boulevard, Moreno Valley, CA
The price is AU$116 per night from 24 Dec to 25 Dec
AU$116
includes taxes & fees
24 Dec - 25 Dec
With a stay at Hotel Xola in Moreno Valley, you'll be within a 10-minute drive of University of California, Riverside and Box Springs Mountain Reserve Park.
Hotel Xola
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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.