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Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

Luxury Estate with Private Pool, close to Temecula Wine Country and Trails

10.0 out of 10, Exceptional, (3)
"Location is spectacular. Very clean and spacious location with lots of fun and luxurious extras. Host is very accommodating and welcoming. Will be booking again in the future. Booked for a small event and had no regrets! Highly recommend! "
Luxury Estate with Private Pool, close to Temecula Wine Country and Trails

Paradise Vacation Estate - Largest Luxury Private Vacation Resort

9.6 out of 10, Exceptional, (188)
"Our stay was AWESOME! Our large family was able to be accommodated. We enjoyed playing pickle ball on the tennis courts. The cool nights were warmed by the spa. The hot days we cooled off in the pool, and we walked the gorgeous lit up grounds at night. Thank you for a wonderful time."
Paradise Vacation Estate - Largest Luxury Private Vacation Resort

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (54)
"Super comfortable and neat space to stay for 3 days! My host was extremely hospitable and answered my questions nearly as quickly as I wrote them!! Highly recommend I would stay again!!!"
The price is AU$204
includes taxes & fees
28 Sept - 29 Sept
1 Bed Room Casita-Suite with Private Entrance

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

10.0 out of 10, Exceptional, (170)
"Wonderful visit, location was great. Property was quiet and so peaceful. Amenities were very nice. We would stay again. "
Walk to Leoness Cellars & Oak Mountain Winery! Heart of Wine Country!

15% Off Oct -Stunning Amenities, Pool, Spa ,Views!

8.8 out of 10, Excellent, (35)
"Great house, met all our needs. "
15% Off Oct -Stunning Amenities, Pool, Spa ,Views!

Wine Country Estate with Vineyard Views, Pool, Spa, Fire-pit, all bedrms w/bath

9.8 out of 10, Exceptional, (97)
"We loved everything about our stay. The house was perfect for a girls family trip. Close to wineries and restaurants. Home is on top of a hill with privacy and great views. Host was responsive. Beds were comfortable. Two people slept on cots for one night and they said they were comfortable. Hot tub heated up quickly! "
Wine Country Estate with Vineyard Views, Pool, Spa, Fire-pit, all bedrms w/bath

Amazing 3600sf Fallbrook San Diego Retreat near Golfing,Wineries,Wedding Venues

9.8 out of 10, Exceptional, (36)
"Stay was good!!"
Amazing 3600sf Fallbrook San Diego Retreat near Golfing,Wineries,Wedding Venues

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

10.0 out of 10, Exceptional, (403)
"Property is quiet and spacious and in excellent condition. About a mile from downtown Idyllwild but very private and away from the bustle of town. "
Fern Valley--the Perfect Spot in Idyllwild Any Time of Year

Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler

9.8 out of 10, Exceptional, (7)
"Property was spacious for two, listing was very accurate. Clean and comfortable casita with an accommodative owner. Would recommend to anyone looking for a place to stay."
The price is AU$202
includes taxes & fees
29 Sept - 30 Sept
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler

The Wine Away-Large Home w/Jacuzzi

10.0 out of 10, Exceptional, (26)
"The property is as show in the pictures and the space was better than we expected. The area was so peaceful and tucked away...a huge kitchen to prep meals and plenty of backyard seating to enjoy. There were a couple of hiccups but I was the property manager was very responsive throughout the time of our stay. "
The Wine Away-Large Home w/Jacuzzi

Stunning Fallbrook Retreat with Private Pool/Spa/Games Room/Fire Pit and More!

10.0 out of 10, Exceptional, (4)
"The property was the perfect accommodations for my family and friends during our weekend getaway to wine country. It was able to sleep all of us comfortably, and both the oversized couch in the living room and outdoor pool were able to fit everyone with room to spare! Watching the sun set over the Fallbrook valley from the backyard was one of my favorite memories from this trip. The property manager was really responsive and tended to all of our requests and questions too. Highly recommend this...
The price is AU$1,023
includes taxes & fees
29 Sept - 30 Sept
Stunning Fallbrook Retreat with Private Pool/Spa/Games Room/Fire Pit and More!

Exclusive Resort Style Estate in Temecula

9.6 out of 10, Exceptional, (33)
"Really fun house that is located close enough to the cute Old Town but so private to head back and enjoy the spa and pool (although the pool was very cold due to the time of the year).A little dated but lots of room for everyone to spread their legs and enjoy.Love the guard cats!"
Exclusive Resort Style Estate in Temecula

Charming dog-friendly home with covered deck, W/D, & mountain view

9.2 out of 10, Wonderful, (19)
"This was a great cabin to stay in and it met all of our family needs!"
Charming dog-friendly home with covered deck, W/D, & mountain view

Walk to Grand Tradition – Pool, Spa & Family-Friendly Retreat>Wine Trips

9.0 out of 10, Wonderful, (8)
"We loved the house, plenty of space for all of us. Host was very responsive and helpful as our plans changed. The kids loved the pool. Very well maintained house and yard.Family is definitely hoping to return."
Walk to Grand Tradition – Pool, Spa & Family-Friendly Retreat>Wine Trips

15%Off Oct 23-26 Close To Wineries, W/Pool & Spa!

9.8 out of 10, Exceptional, (38)
"This property was perfect for our family while in town for our daughter’s wedding. There were 8 of us, perfect space to share."
15%Off Oct 23-26 Close To Wineries, W/Pool & Spa!

20% Off Oct WkDays Near Wineries, W/Pool, Jacuzzi!

9.6 out of 10, Exceptional, (26)
"My wife and I loved staying at this beautiful home snuggled in the middle of wine country. Close to many wineries and a wonderful property...very pet friendly. We will be coming back again!"
20% Off Oct WkDays Near Wineries, W/Pool, Jacuzzi!

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

9.8 out of 10, Exceptional, (70)
"The house was nice and in a great location. The family enjoyed our stay."
Beautiful Storybook Home with hot tub, in the forest. Close to hiking trails.

Hemet Haven, Hot Tub, Heated Pool Option, Backyard, Arcade, Game Room, BBQ Grill

2.0 star property
9.6 out of 10, Exceptional, (7)
"We had a lovely stay in Hemet. The house was very comfortable and we really enjoyed the pool. Checkin and check out were easy and this was the perfect base for us while visiting family. We would definitely stay again. Thanks! "
Hemet Haven, Hot Tub, Heated Pool Option, Backyard, Arcade, Game Room, BBQ Grill

Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views

9.8 out of 10, Exceptional, (105)
"This VRBO was truly amazing. We had a large group & Vlada’s place was perfect. No one felt crowded, plenty of amenities & the kitchen was perfect for preparing large meals. Vlada was very friendly & she made herself available with quick response to any questions or concerns. "
Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views

The Oaktree Estate by Fieldtrip | 7 Acre Private Resort with Lake, Pool & Vineyard

9.2 out of 10, Wonderful, (21)
"The property was amazing! We loved the area, very quiet, clean and Fieldtrip was a great management company. Normal properties give you minimal amenities, this house had so many amenities. It was a great experience!"
The Oaktree Estate by Fieldtrip | 7 Acre Private Resort with Lake, Pool & Vineyard
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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Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
1,240
Accommodation
751 Holiday Homes
Lowest Price
AU$202
Highest Price
AU$1,023

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