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Search results; Over 1,000 places in Winchester

Guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Apr 20 – 25
5.0 out of 5 average rating, 22 reviews
Guest favorite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 beds
May 8 – 13
5.0 out of 5 average rating, 20 reviews
Home in Winchester
Modern Log House
5 beds
May 5 – 10
4.5 out of 5 average rating, 24 reviews
Guest favorite
Home in Winchester
Newly Renovated Cozy Cottage
1 queen bed
Jun 16 – 21
4.9 out of 5 average rating, 184 reviews
Guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
Apr 21 – 26
4.97 out of 5 average rating, 165 reviews
Guest favorite
Home in Winchester
City Charmer minutes from Old Town
2 beds
May 5 – 10
4.97 out of 5 average rating, 212 reviews
Guest favorite
Home in Winchester
Aunt Tim's Farmhouse
6 beds
Apr 21 – 26
4.95 out of 5 average rating, 87 reviews
Guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4 beds
Apr 21 – 26
4.98 out of 5 average rating, 151 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
3 beds
Jun 3 – 8
4.94 out of 5 average rating, 119 reviews
Guest favorite
Home in Winchester
Downtown Chic Condo w/parking
May 5 – 10
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Winchester
Misty Meadow has quite setting in the country.
2 beds
Apr 30 – May 5
4.92 out of 5 average rating, 24 reviews
Home in Winchester
The Herd's Inn
4 beds
Apr 28 – May 3
4.5 out of 5 average rating, 16 reviews
Guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
1 bed
May 19 – 24
4.9 out of 5 average rating, 10 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
Apr 27 – May 2
4.93 out of 5 average rating, 149 reviews
Superhost
Home in Winchester
Stone home in heart of downtown
3 beds
Apr 20 – 25
4.95 out of 5 average rating, 145 reviews
Guest favorite
Home in Winchester
Architect designed downtown flat
2 beds
May 5 – 10
4.95 out of 5 average rating, 22 reviews
Guest favorite
Home in Winchester
Bear Drop Inn on Chestnut Hill with walking trails
7 beds
Apr 22 – 27
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Stephens City
Highland House
5 beds
Apr 22 – 27
5.0 out of 5 average rating, 15 reviews