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Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

Vindemia Estate Vineyard & Winery Guesthouse stay
10.0 out of 10, Exceptional, 3 reviews
"Very nice room on a beautiful small vineyard. Host is very accommodating and quick to respond. Is very close to lots of attractions and nice views. We greatly enjoyed the Vindemia wines and the bar manager was very nice and informative. I greatly recommend this place."
The price is AU$396
includes taxes & fees
26 June - 27 June
Vindemia Estate Vineyard & Winery Guesthouse stay
Rehearsal Dinners Ok*Gated Tuscany Estate Best Ever Wine Co Views
9.4 out of 10, Exceptional, 147 reviews
"Grandeur! Beautiful views and beautiful place to stay with family! Thanks Rochelle💕"
Rehearsal Dinners Ok*Gated Tuscany Estate Best Ever Wine Co Views
Fallbrook Tuscan villa oasis!
9.8 out of 10, Exceptional, 96 reviews
"Overall All of us had a great time The place was immaculate!! Great location , really close to town, Mrs. Dirk was fast to answer our call when we had a question, we really enjoyed the stay, for our next getaway and if we have something planned close by We’d love to stay there again Thank you so very much!!"
Fallbrook Tuscan villa oasis!
Grand Contento by AvantStay | Extraordinary Estate w/ Pool & Movie Room
9.6 out of 10, Exceptional, 16 reviews
"We recently stayed here. Great floor plan with lots of room for a large extended family. We had kids ranging in age from 21 months to 5 years old. This is the 3rd time we rented it. My only wish is that the owner would actually buy a portable fence for the pool, particularly since the home is marketed to families. I have to rent my own each year for an extra $690 !!! Since we have little ones, we cannot take risk of them running out the door when we are not looking and falling into an unfenced...
Grand Contento by AvantStay | Extraordinary Estate w/ Pool & Movie Room
Temecula Valley Retreat Just Minutes From Wine Country
10.0 out of 10, Exceptional, 1 review
"Chris was an amazing host! We had no small children so our stay was perfect and amazing! Comfortable beds and very spacious home!!! I’m a local resident and this home absolute perfect for my family and friends! Amazing time! We will be a rerun guest for sure!!"
Temecula Valley Retreat Just Minutes From Wine Country
❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️
9.0 out of 10, Wonderful, 20 reviews
"This was an amazing place for our girls trip and wine tasting. Owner was amazing and let us drop off our stuff early so it did not sit in our hot cars while we were out wine tasting. The property is so cute, and comfortable, bedrooms and living areas were clean, backyard was amazing."
❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️
Modern Spacious home in Murrieta near Temecula wineries and Historic Old Town
10.0 out of 10, Exceptional, 17 reviews
"We enjoyed our stay at this spacious home. We (4 adults) were traveling to the area for a family wedding. We had plenty of room to spread out, relax on the deck, visit with one another and prepare for the event. Had we been eating/cooking on site instead of at the event we would have felt constrained by the dishes/utensils available for preparing meals. For what we were looking for this weekend this house was great!! We are pleased to have found it to have it as our base for our visit to...
The price is AU$599
includes taxes & fees
18 June - 19 June
Modern Spacious home in Murrieta near Temecula wineries and Historic Old Town
THE BLUE LOTUS Peaceful home for families and buisness getaways.
10.0 out of 10, Exceptional, 26 reviews
"House was clean and easy to navigate to from northern California."
THE BLUE LOTUS Peaceful home for families and buisness getaways.
Tranquil Holiday Estate with Pool/Spa 6b4b
The price is AU$1,691
includes taxes & fees
16 June - 17 June
Tranquil Holiday Estate with Pool/Spa 6b4b
Dog-friendly mountain retreat with private hot tub & well-appointed deck
9.6 out of 10, Exceptional, 133 reviews
"We had a wonderful time. The place was charming, clean and very comfortable. Two small things: 1) There was s very strong sewer smell coming from under the deck near the kitchen door. We tried to locate it but couldn’t pinpoint. 2) There is only one broken ice tray. We recommend replacing it. If we were staying longer I would have bought a couple as a house gift!😁"
Dog-friendly mountain retreat with private hot tub & well-appointed deck
Luxury Tropical Modern Villa Pool Jacuzzi Game Room
Luxury Tropical Modern Villa Pool Jacuzzi Game Room
A premier rental estate with an ample array of amenities & outdoor lounge areas
10.0 out of 10, Exceptional, 172 reviews
"The outdoor amenities are excellent. The kitchen and bathroom plumbing need attention."
A premier rental estate with an ample array of amenities & outdoor lounge areas
Mansion on De Portola with Vineyard and Mountain view
10.0 out of 10, Exceptional, 26 reviews
"Our group of 9 had an incredible stay on this beautiful property! We came for a work retreat and enjoyed all aspects of the home and view. We spent our days working and playing out by the pool and evenings out by the fire pit talking under the stars. The interior of the home is dreamy, gorgeous stone fireplace and giant dining room table to host us all. Everyone mentioned how comfy the beds were and how everything we needed was there, from toiletries to laundry detergent, dishwasher pods, etc....
The price is AU$2,059
includes taxes & fees
1 July - 2 July
Mansion on De Portola with Vineyard and Mountain view
Hill Top Estate In The Heart Of The Wine Country W/incredible Views!!
10.0 out of 10, Exceptional, 87 reviews
"Lovely home inside and out. The view was marvelous"
Hill Top Estate In The Heart Of The Wine Country W/incredible Views!!
Fern Valley--the Perfect Spot in Idyllwild any Time of Year
10.0 out of 10, Exceptional, 362 reviews
"👍"
Fern Valley--the Perfect Spot in Idyllwild any Time of Year
Villa with great view/pool/spa
10.0 out of 10, Exceptional, 12 reviews
"We had an absolutely amazing stay at this villa.The host was warm and welcoming, providing clear instructions and allowing us to check in early and bring my dogs (all last minute). The property was clean and beautifully decorated, creating a cozy and inviting atmosphere. The amenities were thoughtful, including a fully equipped kitchen, fast Wi-Fi, and plenty of towels! The location was great and really close to the wineries. Overall, my family and I had an amazing weekend and a really great...
The price is AU$2,061
includes taxes & fees
18 June - 19 June
Villa with great view/pool/spa
Private protected oak grove with stream only 10 minutes to Old Town Temecula
9.6 out of 10, Exceptional, 22 reviews
"Our host Emily was very responsive and kind. The RV itself had everything we needed to be more than comfortable. Cold but heated up nicely with the fireplace and room heaters provided. Appreciated that things were labeled with where to find things like extra blankets, oven out of order, etc. we had a fun time overall! Area was secluded and quiet, beautiful grove to walk around and let our dog explore! We did find a few ticks on her after so would recommend long pants and checking pets and...
The price is AU$262
includes taxes & fees
11 July - 12 July
Private protected oak grove with stream only 10 minutes to Old Town Temecula
Wine Country Blue Lagoon - Pool - Firepit - Close to Wineries
10.0 out of 10, Exceptional, 95 reviews
"Great experience. Hosts were very communicative with any questions we had. The house has a great layout with plenty of space for a group of people!"
Wine Country Blue Lagoon - Pool - Firepit - Close to Wineries
Wine in Doubt, Catch a Red I - Active Winery Home
9.8 out of 10, Exceptional, 34 reviews
"Beautiful and well maintained property. Its perfect for multiple group pods. Everyone had their own cute area"
Wine in Doubt, Catch a Red I - Active Winery Home
The Whiskey Cavern in Fallbrook-2 homes
10.0 out of 10, Exceptional, 3 reviews
"Great space to hang out after golfing all day! We enjoyed the shuffleboard and darts. Will stay again!"
The Whiskey Cavern in Fallbrook-2 homes
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See all available properties in Winchester
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.

Other property types in Winchester

Chateau Vino - French Style Chalet
10.0 out of 10, Exceptional, 30 reviews
"I wanted to take a moment to express my sincerest gratitude for the exceptional hospitality and the beautiful accommodation during our recent stay at your property. First and foremost, I must say that our experience was simply fantastic. From the moment we arrived, we were captivated by the beauty and charm of the property. It truly exceeded our expectations, and we were delighted to find ourselves in such a serene and welcoming environment. I cannot go without mentioning how amazing Ms....
Chateau Vino - French Style Chalet
Wine Country Oasis Retreat - Close to wineries
10.0 out of 10, Exceptional, 34 reviews
"Beautiful house with everything you need, home away from home. We had two families, 4 adults, 4 kids and a dog. Eric was available for any questions. We had some issues with the pool, but Eric got on it right away and we worked with him to get it fixed. We enjoyed the pool table and outdoor fire pit. The living room was big enough for all of us to watch movies. The bed in the master was super comfortable. Loved that the bathroom had little toothpastes and soap. Plenty of soap for laundry too."
Wine Country Oasis Retreat - Close to wineries
The Cottages at Golden Village Palms
3.0 star property
9.6 out of 10, Exceptional, 30 reviews
"Check in process was super easy. Friendly and helpful staff. Cute, small accommodations. Great for a quick overnight or two. "
The price is AU$248
includes taxes & fees
16 June - 17 June
The Cottages at Golden Village Palms
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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