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Winchester Holiday Rentals

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47 rentals in Winchester.
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Cozy Bungalow near Temecula * Rising Son Ranch, holiday rental in Winchester

Cozy Bungalow near Temecula * Rising Son Ranch

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Secluded Euro Style Cabin near Temecula * Rising Son Ranch, holiday rental in Winchester

Secluded Euro Style Cabin near Temecula * Rising Son Ranch

2 bedrooms
2 bathrooms
Sleeps 6
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The Modern Farmhouse * Rising Son Ranch near Temecula w/ Pool & Spa, holiday rental in Winchester

The Modern Farmhouse * Rising Son Ranch near Temecula w/ Pool & Spa

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Rising Son Ranch 4.5 Acre Estate-3 Homes w/ Resort Style Pool & Spa, holiday rental in Winchester

Rising Son Ranch 4.5 Acre Estate-3 Homes w/ Resort Style Pool & Spa

7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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NEW! Hilltop Hideaway in the Heart of Wine Country, holiday rental in Winchester

NEW! Hilltop Hideaway in the Heart of Wine Country

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern 5 Acre Retreat in the Heart of Wine Coutry, holiday rental in Winchester

Modern 5 Acre Retreat in the Heart of Wine Coutry

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Boutique Winery Getaway, holiday rental in Winchester

Boutique Winery Getaway

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Arena in Temecula Wine Country, holiday rental in Winchester

The Arena in Temecula Wine Country

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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GREAT LOCATION! CLOSE TO PELTZER, LORIMAR, FAULKNER, LONG SHADOW WINERIES!, holiday rental in Winchester

GREAT LOCATION! CLOSE TO PELTZER, LORIMAR, FAULKNER, LONG SHADOW WINERIES!

4 bedrooms
4 bathrooms
Sleeps 14
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Your suite has a private patio with a view of the vineyard and the hill sides, holiday rental in Winchester

Your suite has a private patio with a view of the vineyard and the hill sides

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Calle Cabernet Vineyard Retreat, holiday rental in Winchester

Calle Cabernet Vineyard Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Lodge with an Amazing View, holiday rental in Winchester

Lakefront Lodge with an Amazing View

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Welcome To The Beautiful San Jacinto Valley, holiday rental in Winchester

Welcome To The Beautiful San Jacinto Valley

4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Escape to a Quiet Sunny Retreat (55 & Older)  2 BR Menifee Ca, holiday rental in Winchester

Escape to a Quiet Sunny Retreat (55 & Older) 2 BR Menifee Ca

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Old West Temecula Wine Country Vacation Rental, holiday rental in Winchester

Old West Temecula Wine Country Vacation Rental

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Temecula Wine Country for Nature Lovers, Wine drinkers and Relaxation, holiday rental in Winchester

Temecula Wine Country for Nature Lovers, Wine drinkers and Relaxation

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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#4- 5BR/3BTH 4000’ HUGE VILLA W/ VIEWS, OUTDOOR DINING, BBQ, FIREPLACE, GAMES**, holiday rental in Winchester

#4- 5BR/3BTH 4000’ HUGE VILLA W/ VIEWS, OUTDOOR DINING, BBQ, FIREPLACE, GAMES**

5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Luxe & Private 3bd/2ba Wine Country Getaway, holiday rental in Winchester

Luxe & Private 3bd/2ba Wine Country Getaway

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relax in Temecula/Murrieta, holiday rental in Winchester

Relax in Temecula/Murrieta

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Creekside Cab - Walking distance to Wilson Creek, holiday rental in Winchester

Creekside Cab - Walking distance to Wilson Creek

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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WINE COUNTRY 2 BEDROOM CASITA, holiday rental in Winchester

WINE COUNTRY 2 BEDROOM CASITA

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vintners View Farmhouse, holiday rental in Winchester

Vintners View Farmhouse

2 bedrooms
2 bathrooms
Sleeps 5
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Navarro Estate, holiday rental in Winchester

Navarro Estate

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Discover Private Lake Getaway - SoCal Wine Country near Temecula, holiday rental in Winchester

Discover Private Lake Getaway - SoCal Wine Country near Temecula

4 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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Baird Family Trailer, holiday rental in Winchester

Baird Family Trailer

2 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Palm Springs/Temecula Winery, holiday rental in Winchester

Palm Springs/Temecula Winery

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Spend Your Vacation In A Cozy Beautiful Home, holiday rental in Winchester

Spend Your Vacation In A Cozy Beautiful Home

1 bedroom
1 bathroom
Sleeps 2
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scenic get away, holiday rental in Winchester

scenic get away

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hemet House with a pool. 3 bedroom, 2 bath. Private, holiday rental in Winchester

Hemet House with a pool. 3 bedroom, 2 bath. Private

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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❤️Skydiver's, Business & Traveler's 1st Choice!❤️, holiday rental in Winchester

❤️Skydiver's, Business & Traveler's 1st Choice!❤️

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Luxe Wine Country Estate w/ Orchard-Facing Balcony, holiday rental in Winchester

Luxe Wine Country Estate w/ Orchard-Facing Balcony

4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Your Home Away From Home on the Lake, holiday rental in Winchester

Your Home Away From Home on the Lake

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Sun-Splashed Skyline Sanctum/Near Temecula Wineries, holiday rental in Winchester

Sun-Splashed Skyline Sanctum/Near Temecula Wineries

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relaxing Wine Country Estate w/BAR+SPA+POOL+BBQ+VBALL+SOCCER, holiday rental in Winchester

Relaxing Wine Country Estate w/BAR+SPA+POOL+BBQ+VBALL+SOCCER

5 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Beautiful Golf Course view home in Menifee Greens!, holiday rental in Winchester

Beautiful Golf Course view home in Menifee Greens!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stone Creek Ranch Temecula Wine Country, holiday rental in Winchester

Stone Creek Ranch Temecula Wine Country

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wine Country Home Near Beach, LA and San Diego, holiday rental in Winchester

Wine Country Home Near Beach, LA and San Diego

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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San Jacinto Country Club Home w/ Amenities!, holiday rental in Winchester

San Jacinto Country Club Home w/ Amenities!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Serenity - for sun, relaxation & fun, holiday rental in Winchester

Casa Serenity - for sun, relaxation & fun

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Canyon Lake Home w/ Jacuzzi, 1 Mile to Sierra Park, holiday rental in Winchester

Canyon Lake Home w/ Jacuzzi, 1 Mile to Sierra Park

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxe & Clean 3bd/2ba Wine Country Getaway, holiday rental in Winchester

Luxe & Clean 3bd/2ba Wine Country Getaway

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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CasaVino Tropical Retreat - Wine Country Oasis, holiday rental in Winchester

CasaVino Tropical Retreat - Wine Country Oasis

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Green Room with Shared Bathroom, holiday rental in Winchester

Green Room with Shared Bathroom

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful 3 Bedroom Oasis, holiday rental in Winchester

Beautiful 3 Bedroom Oasis

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious remodeled 2bd/1ba house with huge yard, holiday rental in Winchester

Spacious remodeled 2bd/1ba house with huge yard

2 bedrooms
1 bathroom
Sleeps 49
Match: Sleeps
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NEW! Tasteful Temecula Home: Private Pool & Views!, holiday rental in Winchester

NEW! Tasteful Temecula Home: Private Pool & Views!

1 bedroom
4 bathrooms
Sleeps 10
Match: Sleeps
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TEMECULA VALLEY WINE COUNTRY POOL/SPA HOME, holiday rental in Winchester

TEMECULA VALLEY WINE COUNTRY POOL/SPA HOME

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Traveling fields students and long-term there are two shared bathrooms, holiday rental in Winchester

Traveling fields students and long-term there are two shared bathrooms

1 bedroom
2 bathrooms
Sleeps 1
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Students and traveling field super discount there are two bathrooms shared, holiday rental in Winchester

Students and traveling field super discount there are two bathrooms shared

1 bedroom
2 bathrooms
Sleeps 1
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