Over 1,000 places in Stephenson

Guest favorite
Cottage in Winchester
Emma's Stone Cottage
3 beds
Apr 21 – 26
4.97 out of 5 average rating, 421 reviews
Guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Apr 20 – 25
5.0 out of 5 average rating, 22 reviews
Superhost
Guesthouse in Winchester
Welcome to a Perfect Night Stay!
Apr 20 – 25
New place to stay
Guest favorite
Home in Winchester
Newly Renovated Cozy Cottage
1 queen bed
Jun 16 – 21
4.9 out of 5 average rating, 184 reviews
Apartment in Bunker Hill
Apartment in Bunker Hill
Apr 21 – 26
New place to stay
Guest favorite
Guest suite in Clear Brook
Bluebird Bungalow
2 beds
Apr 29 – May 4
5.0 out of 5 average rating, 37 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
Guest favorite
Cottage in Winchester
Lockley Cottage at Historic Perry Farm
2 beds
Jul 15 – 20
4.9 out of 5 average rating, 98 reviews
Guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4 beds
May 6 – 11
4.98 out of 5 average rating, 151 reviews
Guest favorite
Cabin in Gerrardstown
The Nest: Cozy Chalet w/Wi-Fi, Deck & Grill
3 beds
Apr 21 – 26
5.0 out of 5 average rating, 97 reviews
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station
1 queen bed
Apr 21 – 26
4.94 out of 5 average rating, 270 reviews
Superhost
Barn in Berryville
Modern House Barn on 66 acre Horse Farm
3 beds
Apr 20 – 25
4.8 out of 5 average rating, 84 reviews
Guest favorite
Guest suite in Summit Point
The Big Room - Historic Schoolhouse
1 king bed
Apr 21 – 26
4.97 out of 5 average rating, 128 reviews
Guest favorite
Farm stay in Berryville
The Barns at Senseny Cottage
7 beds
Apr 21 – 26
4.9 out of 5 average rating, 60 reviews
Guest favorite
Cottage in Winchester
Modern 3BR country farmhouse
6 beds
Apr 19 – 24
5.0 out of 5 average rating, 19 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
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
May 13 – 18
5.0 out of 5 average rating, 137 reviews
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
Apr 19 – 24
4.93 out of 5 average rating, 40 reviews