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Compare 115 Vacation Homes in Winchester with updated reviews, rates, and availability.

Bright three-level home with water views, jetted tub, firepit, and pool table
Bright three-level home with water views, jetted tub, firepit, and pool table
8.4 out of 10, Very Good, (27)

Family Friendly Hilltop House In Putney Vermont
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, (54)
The price is SAR 731
SAR 1,281 total
includes taxes & fees
23 Mar - 24 Mar

1810 Brook Side Mill/House / EV Level 2 Charging on Site
1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, (71)

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, (15)

GAMERS HAVEN, River Wine Inn!
GAMERS HAVEN, River Wine Inn!
10.0 out of 10, Exceptional, (7)

Lovely 2nd Floor Apartment
Lovely 2nd Floor Apartment
9.8 out of 10, Exceptional, (19)
The price is SAR 484
SAR 813 total
includes taxes & fees
23 Mar - 24 Mar

Hilltop Home with Great Views
Hilltop Home with Great Views
9.2 out of 10, Wonderful, (12)

The Jelly Mill-A River Retreat
The Jelly Mill-A River Retreat
10.0 out of 10, Exceptional, (45)
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

The Jelly Mill-A River Retreat
The Jelly Mill-A River Retreat
10.0 out of 10, Exceptional, (45)

Cozy Home Near Downtown, Shops, and Restaurants.
Cozy Home Near Downtown, Shops, and Restaurants.
10.0 out of 10, Exceptional, (3)
The price is SAR 1,125
SAR 1,950 total
includes taxes & fees
3 Apr - 4 Apr

Riverfront 2 Bedroom Unit 2
Riverfront 2 Bedroom Unit 2
9.8 out of 10, Exceptional, (16)
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

The Putney Inn
5/5 Excellent
"My stay was good, the only thing I did not like was the windows not having curtains despite them being higher up. I did not feel comfortable enough to take a shower. It was very awkward having a window in the bathroom, let alone not having a curtain to close. "
A verified traveler stayed at The Putney Inn
Posted 4 days ago