Book Holiday Homes in Winchester

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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
Stay at this vacation home in Temecula. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Pechanga Resort & Casino and Rancho Palomar ...
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
Book a stay at this family-friendly vacation home in Temecula. Enjoy free WiFi, private pools, and a water park. Popular attractions Wilson Creek Winery and ...
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
Book a stay at this family-friendly vacation home in Temecula. Enjoy free WiFi, a garden, and patios. Popular attractions Pechanga Resort & Casino and Rancho ...
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
Book a stay at this family-friendly vacation home in Idyllwild. Enjoy free WiFi, a fitness center, and patios. Popular attractions Idyllwild Park and Idyllwild ...
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
Stay at this vacation home in Idyllwild. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Idyllwild Nature Center and Idyllwild Park ...
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
Book a stay at this family-friendly vacation home in Winchester. Enjoy free WiFi, a water park, and a garden. Popular attractions Wilson Creek Winery and Monte ...
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
Book a stay at this family-friendly vacation home in Temecula. Enjoy free WiFi, private pools, and a garden. Popular attractions Pechanga Resort & Casino and ...
Private Wine Country estate with 360 view of Temecula Valley
Sprawling California Ranch House w/ Courtyard!

Sprawling California Ranch House w/ Courtyard!

Temecula
Stay at this vacation home in Temecula. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Pechanga Resort & Casino and Galway ...
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
Stay at this vacation home in Fallbrook. Enjoy private pools, a sauna, and a garden. Popular attractions Pechanga Resort & Casino and 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
581 Holiday Homes
Lowest Price
NZ$129
Highest Price
NZ$191
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 NZ$188 per night from 23 Dec to 24 Dec
NZ$188
includes taxes & fees
23 Dec - 24 Dec
Stay at this 4-star hotel in Pala. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the bar and the helpful staff in our reviews. Popular ...
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 NZ$143 per night from 24 Dec to 25 Dec
NZ$143
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this business-friendly hotel in Temecula. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 NZ$191 per night from 23 Dec to 24 Dec
NZ$191
includes taxes & fees
23 Dec - 24 Dec
Stay at this hotel in Idyllwild. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 NZ$129 per night from 24 Dec to 25 Dec
NZ$129
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this business-friendly hotel in Moreno Valley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
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.