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Search Vacation Homes in Winchester
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Compare 109 Vacation Homes in Winchester with updated reviews, rates, and availability.
![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/a477d14d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Lovely 2nd Floor Apartment
Lovely 2nd Floor Apartment
9.8 out of 10, Exceptional, (18)
The price is AED 474
AED 792 total
includes taxes & fees
18 Feb - 19 Feb
![Plenty of private open space to explore with the whole family!](https://images.trvl-media.com/lodging/72000000/71940000/71933600/71933561/4c2b8517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (51)
![Exterior](https://images.trvl-media.com/lodging/47000000/46230000/46227400/46227357/3df8f42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Cozy cottage tucked away in the woods
Cozy cottage tucked away in the woods
10.0 out of 10, Exceptional, (41)
![Exterior](https://images.trvl-media.com/lodging/82000000/81870000/81865200/81865142/41ad7912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Charming Waterfront Log Cabin
Charming Waterfront Log Cabin
9.6 out of 10, Exceptional, (37)
![Exterior](https://images.trvl-media.com/lodging/36000000/35570000/35563200/35563104/36e60d34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Hilltop Home with Great Views
Hilltop Home with Great Views
9.2 out of 10, Wonderful, (12)
![Exterior detail](https://images.trvl-media.com/lodging/107000000/106260000/106259100/106259002/91c33f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
River House
River House
10.0 out of 10, Exceptional, (7)
![](https://images.trvl-media.com/lodging/111000000/110740000/110733400/110733301/91b0ce9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
The Dover Hideaway | Hot Tub & Close to Mt. Snow
The Dover Hideaway | Hot Tub & Close to Mt. Snow
![Front View of The Thrushwood Estate](https://images.trvl-media.com/lodging/34000000/33570000/33566000/33565969/118b2cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
10.0 out of 10, Exceptional, (65)
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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Other property types in Winchester
![Winter wonderland!](https://images.trvl-media.com/lodging/19000000/19000000/18993600/18993521/410a87c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
9.8 out of 10, Exceptional, (113)
![](https://images.trvl-media.com/lodging/91000000/90290000/90288000/90287973/539a7a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
7.0 out of 10, Good, (14)
![Plenty of private open space to explore with the whole family!](https://images.trvl-media.com/lodging/72000000/71940000/71933600/71933561/4c2b8517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (51)
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.
Recent reviews of Winchester hotels
Recent reviews of Winchester hotels
![Fairfield Inn & Suites by Marriott Keene Downtown](http://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7_y.jpg)
Fairfield Inn & Suites by Marriott Keene Downtown
5/5 Excellent
"It was a fabulous weekend...thank you ❤️ "
A verified traveler stayed at Fairfield Inn & Suites by Marriott Keene Downtown
Posted 1 day ago