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3RV/ parking/Netflix/ private/excellent location

8.4 out of 10, Very good, (7)
"Very clean Owners were very sweet and helpful. "
The price is HK$381
HK$965 total
includes taxes & fees
9 Oct - 10 Oct
3RV/ parking/Netflix/ private/excellent location

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 HK$245
HK$853 total
includes taxes & fees
14 Oct - 15 Oct
1 Bed Room Casita-Suite with Private Entrance

Beautiful lodge on creek, full bath, AC, WiFi, many amenities! Hot tub views!

10.0 out of 10, Exceptional, (1)
"Great location and property. Tara was very accommodating and hospitable. "
The price is HK$817
HK$1,424 total
includes taxes & fees
6 Oct - 7 Oct
Beautiful lodge on creek, full bath, AC, WiFi, many amenities! Hot tub views!

The Pony Experience Farm Stay! 501c3

8.4 out of 10, Very good, (5)
"Me and my daughter couldn’t have asked for a better experience. Hosts were attentive to us and the animals were AMAZING to be around. Horses, peacocks, dogs, fowl, all very welcoming and happy to have guests around. I just wish…nothing. It was great. Very serene too."
The price is HK$1,938
HK$2,451 total
includes taxes & fees
3 Nov - 4 Nov
The Pony Experience Farm Stay! 501c3

•Charming One-Level Home • Feels Like Home

The price is HK$2,840
HK$4,366 total
includes taxes & fees
6 Oct - 7 Oct
•Charming One-Level Home • Feels Like Home

Ranch House Interior - 4 bedroom, 4 bath home on-site of Galway Downs

10.0 out of 10, Exceptional, (2)
"This place was great, we were able to fit 10 people and have a spare bed. The only thing I would note is that the showers do not have a door to the bedroom so for a group sharing a room (I.e. the rooms with 2 queen beds) you would have to be mindful of this. Otherwise, great space with spacious central area. Host was responsive and allowed early check in."
The price is HK$4,708
HK$6,755 total
includes taxes & fees
27 Oct - 28 Oct
Ranch House Interior - 4 bedroom, 4 bath home on-site of Galway Downs

Bright Airy 5B Home Workspace Outdoor Lounge

2.0 star property
The price is HK$2,177
HK$4,834 total
includes taxes & fees
19 Oct - 20 Oct
Bright Airy 5B Home Workspace Outdoor Lounge

Lakeside Escape, Cozy Getaway

2.0 star property
The price is HK$679
HK$1,107 total
includes taxes & fees
12 Oct - 13 Oct
Lakeside Escape, Cozy Getaway

Spacious Sanctuary: Creek Access, Tesla Charger, Hammocks, Fire Pit, Pets OK

10.0 out of 10, Exceptional, (7)
"It was the cutest place so clean and had everything we needed. Close enough to town and far enough to feel like your were in the woods. Loved it. Would definitely come back "
The price is HK$1,167
HK$2,564 total
includes taxes & fees
15 Oct - 16 Oct
Spacious Sanctuary: Creek Access, Tesla Charger, Hammocks, Fire Pit, Pets OK

La Petite - Heart of Town - Stunning Remodel

10.0 out of 10, Exceptional, (13)
"The property is upgraded, had everything we needed, dog friendly, and super close to town. Would definitely stay here again!"
The price is HK$973
HK$3,844 total
includes taxes & fees
6 Oct - 7 Oct
La Petite - Heart of Town - Stunning Remodel

Resort-style Home with stunning views, pool, hot tub, putting green

10.0 out of 10, Exceptional, (11)
"What an amazing house! Everything was perfect. All the details within the listing were accurate. Plenty of room for everyone. When looking for a vacation home to rent in Fallbrook, look no further!!! We would rent again."
The price is HK$2,101
HK$6,328 total
includes taxes & fees
6 Oct - 7 Oct
Resort-style Home with stunning views, pool, hot tub, putting green

Private European Vineyard w/ Secluded Hilltop Views in Wine Country

9.8 out of 10, Exceptional, (13)
"This place was awesome. Great views, peaceful. The host jerry was very easy to work with excellent communication.No problems"
The price is HK$3,356
HK$7,768 total
includes taxes & fees
8 Oct - 9 Oct
Private European Vineyard w/ Secluded Hilltop Views in Wine Country

BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY

2.0 star property
9.8 out of 10, Exceptional, (8)
"We enjoyed our stay , host was great and location also very calm and beautiful, recommend 10/10"
The price is HK$1,945
HK$4,716 total
includes taxes & fees
6 Oct - 7 Oct
BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY

Serene Vineyard Cottage Escape

10.0 out of 10, Exceptional, (1)
"Our stay was amazing! We were in town for a friend's wedding so we were pretty busy and did not use the pool but wish we had the time. The cottage itself was secluded and quiet. The views were gorgeous! The bed was comfortable and we had everything we needed in the kitchen. We only did some minor cooking. Luann, the host, was so sweet and provided us some great recommendations for restaurants. If we would visit the area again, I would 100% stay there again and recommend it to others. "
The price is HK$1,357
HK$2,890 total
includes taxes & fees
6 Oct - 7 Oct
Serene Vineyard Cottage Escape

Peach Blossom Country House

9.2 out of 10, Wonderful, (5)
"My stay was very nice and quiet. Didn't have to worry about my safety and stores were very close to the property. The host was very accommodating and responsive. I would recommend staying at this property."
The price is HK$1,296
HK$2,650 total
includes taxes & fees
6 Oct - 7 Oct
Peach Blossom Country House

Above the Clouds 17acre Gated Lux Estate 360 Views

2.0 star property
7.4 out of 10, Good, (3)
"This place is like a sanctuary in the mountains! The house is so cozy with a beautiful kitchen for cooking and the sauna was a great amenity. My kids absolutely loved the game room downstairs and the pool. The host was great and responsive. Don’t miss out on this place! "
The price is HK$2,794
HK$6,926 total
includes taxes & fees
7 Oct - 8 Oct
Above the Clouds 17acre Gated Lux Estate 360 Views

Beautifully remodeled mountain home with peaceful, private setting

8.8 out of 10, Excellent, (72)
"Super clean and comfy beds. Bath towels were super soft and they have to BEST smelling body wash. Top-notch kitchen appliances! Quiet and peaceful. We got a kick out of watching the squirrels playing from the living room window."
The price is HK$747
HK$2,425 total
includes taxes & fees
6 Oct - 7 Oct
Beautifully remodeled mountain home with peaceful, private setting

Charming working ranch in the heart of Temecula wine country

10.0 out of 10, Exceptional, (5)
"Fully equipped family friendly house fully in a peaceful area. "
The price is HK$1,183
HK$2,359 total
includes taxes & fees
9 Oct - 10 Oct
Charming working ranch in the heart of Temecula wine country

Family Mountain Home! Hot Tub, Gameroom, Privacy. Dogs free! Wedding venues.

10.0 out of 10, Exceptional, (16)
"Had a small family get together place was amazing great games lots of space inside and out highly recommended "
Family Mountain Home! Hot Tub, Gameroom, Privacy. Dogs free! Wedding venues.
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 Vacation Homes information

Number of reviews
126
Accommodation
760 Vacation Homes
Lowest Price
HK$853
Highest Price
HK$7,768