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Compare 744 Vacation Homes in Winchester with updated reviews, rates, and availability.

Welcome to Love at First Syrah! Single Story home w/pool/spa/ 7 bedrooms & more!

Welcome to Love at First Syrah! Single Story home w/pool/spa/ 7 bedrooms & more!

Fern Valley--the Perfect Spot in Idyllwild Any Time of Year

10.0 out of 10, Exceptional, (395)
"We loved our time in this wonderful cabin. It was the cozy, comforting, quiet and exactly what we were hoping for! We also loved the convenience of hiking trails right close by, and our animals loved the place too! Our host was very responsive and welcoming. Will definitely look to stay again next time we come to Idyllwild."
Fern Valley--the Perfect Spot in Idyllwild Any Time of Year

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (42)
"Perfect for a quick overnight stay. "
The price is AEDĀ 192
AEDĀ 486 total
includes taxes & fees
9 Jun - 10 Jun
1 Bed Room Casita-Suite with Private Entrance

15% Off May Dates -Close To Wineries W/Pool & Spa!

9.8 out of 10, Exceptional, (29)
"Close to wineries, enjoyed the amenities"
15% Off May Dates -Close To Wineries W/Pool & Spa!

Walk to Leoness Cellars & Oak Mountain Winery! Heart of Wine Country!

10.0 out of 10, Exceptional, (157)
"We had a wonderful stay at this beautiful home. It was well stocked and the location was great. Would definitely stay there again!"
Walk to Leoness Cellars & Oak Mountain Winery! Heart of Wine Country!

Luxury Gated Estate with Views of All of Wine Country!

9.6 out of 10, Exceptional, (178)
"Thanks for letting us stay the place was amazing as always!"
Luxury Gated Estate with Views of All of Wine Country!

The Whiskey Cavern in Fallbrook

9.8 out of 10, Exceptional, (9)
"Great property with all the amenities of home! "
The Whiskey Cavern in Fallbrook

30% Off May 28-31 - 6Br,Close to Town and Wineries

10.0 out of 10, Exceptional, (2)
"My friends and I stayed here for my birthday celebration and it was truly a wonderful experience! The property is stunning, easy to locate and was a overall perfect place to enjoy a weekend away. The location was wonderful for a peaceful cup of coffee in the morning followed by a quick 20-30 minute drive to all of the the wineries in Temecula. The host was extremely accommodating and let us check in early and check out late. My only recommendation would be to ensure you download the lock box and...
30% Off May 28-31 - 6Br,Close to Town and Wineries

15% Off May Dates - Stunning Amenities, Pool,Spa ,Views!

9.4 out of 10, Exceptional, (27)
"Perfect for a 3 day getaway"
15% Off May Dates - Stunning Amenities, Pool,Spa ,Views!

Villa Vigna (Gorgeous Mountain View with Private Pool!)

9.8 out of 10, Exceptional, (62)
"Had a wonderful stay over Thanksgiving weekend. Property manager was amazing and extremely responsive to all our needs. We will stay here again! "
Villa Vigna (Gorgeous Mountain View with Private Pool!)

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

9.8 out of 10, Exceptional, (63)
"Amazing time in a fabulous location!"
Beautiful Storybook Home with hot tub, in the forest. Close to hiking trails.

The best view in Temecula Wine Country!

10.0 out of 10, Exceptional, (34)
"We enjoyed our stay. Extremely peaceful and tranquil location."
The best view in Temecula Wine Country!

Inspiring home with "Sunset Perch" Views & Spa

8.2 out of 10, Very Good, (49)
"We spent a really good time. The view and the deck were amazing. Very cozy cabin. One thing that I have to say, is that some of the furnitures were old. But in general we love our stay there. "
Inspiring home with "Sunset Perch" Views & Spa

Wine Country Cottage W/Amazing Pano-Valley Views!

9.6 out of 10, Exceptional, (23)
"Communication was great with property manager and check in was easy."
Wine Country Cottage W/Amazing Pano-Valley Views!

Time to Wine Down-Horse stables and trails

9.6 out of 10, Exceptional, (21)
"We had an amazing stay! House so super nice, great for large groups! Host was super attentive & great communication! "
Time to Wine Down-Horse stables and trails

Amazing 1st-floor guest suite on secure estate near wine country!

10.0 out of 10, Exceptional, (23)
"Very clean and comfortable stay. "
The price is AEDĀ 804
AEDĀ 1,230 total
includes taxes & fees
2 Jul - 3 Jul
Amazing 1st-floor guest suite on secure estate near wine country!

Home on Organic Farm Near Wine Country and Casinos

9.4 out of 10, Exceptional, (36)
"Enjoyed our stay. A bit away from the beach scene, but nice and quiet."
Home on Organic Farm Near Wine Country and Casinos

Breathtaking view with a heated lap pool

9.0 out of 10, Wonderful, (22)
"We had a great time! House was perfect for our needs!"
Breathtaking view with a heated lap pool

Mediterranean Estate - FREE SOLAR HEATED POOL Apr 15-Oct 15,plus optional Casita

9.8 out of 10, Exceptional, (111)
"Great for family/friends attending weddings so people are all together! This place was perfect!"
Mediterranean Estate - FREE SOLAR HEATED POOL Apr 15-Oct 15,plus optional Casita

Diamond Retreat-Kid & Pet Friendly.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Wonderful location and experience will try and book again"
Diamond Retreat-Kid & Pet Friendly.
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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