137 places in Winchester

Guest favorite
Tiny home in Winchester
The Overlook: A Sweetwater Stay
2 beds
May 11 – 16
4.98 out of 5 average rating, 65 reviews
Guest favorite
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - entire home
5 beds
Apr 22 – 27
5.0 out of 5 average rating, 22 reviews
Guest favorite
Tiny home in Orange
The Photographer's Hut: A Sweetwater Stay
1 queen bed
May 12 – 17
4.93 out of 5 average rating, 300 reviews
Guest favorite
Tiny home in Brattleboro
Sweet Vermont Tiny Home Get Away
1 double bed
Apr 26 – May 1
4.94 out of 5 average rating, 34 reviews
Guest favorite
Barn in Guilford
The Carriage Barn
4 beds
Apr 29 – May 4
4.99 out of 5 average rating, 95 reviews
Guest favorite
Treehouse in Guilford
Cozy tent in the trees on organic flower farm
1 queen bed
Apr 21 – 26
4.99 out of 5 average rating, 82 reviews
Guest favorite
Tiny home in Orange
The Writer's Retreat: A Sweetwater Stay
1 queen bed
Apr 28 – May 3
4.92 out of 5 average rating, 310 reviews
Guest favorite
Barn in Marlboro
The Studio With a View. Bring your dog, too!
2 beds
Apr 23 – 28
4.95 out of 5 average rating, 263 reviews
Guest favorite
Farm stay in Brattleboro
Modern Vermont Farm Stay
2 single beds
May 2 – 7
4.93 out of 5 average rating, 70 reviews
Guest favorite
Barn in Brattleboro
Sunny barn apartment 4 minute walk from downtown
1 king bed
Apr 28 – May 3
4.92 out of 5 average rating, 49 reviews
Superhost
Tiny home in Brattleboro
“Sugar Maple” Rustic Cabin Getaway with Fireplace
2 beds
May 2 – 7
4.86 out of 5 average rating, 164 reviews
Guest favorite
Farm stay in Stoddard
Upton Farm and Forest
May 1 – 6
5.0 out of 5 average rating, 77 reviews
Guest favorite
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - first floor
2 beds
Apr 22 – 27
4.96 out of 5 average rating, 48 reviews
Guest favorite
Tiny home in Putney
Honeycrisp Cottage - A Tiny Timber Frame
2 beds
Apr 30 – May 5
4.95 out of 5 average rating, 669 reviews
Guest favorite
Farm stay in West Brattleboro
Lilac Ridge Farm House
4 beds
May 2 – 7
4.93 out of 5 average rating, 122 reviews
Guest favorite
Tiny home in Brattleboro
Brattleboro Tiny House
2 queen beds
Apr 25 – 30
4.89 out of 5 average rating, 9 reviews
Guest favorite
Tiny home in Jamaica
Apple Blossom Cottage: A Tiny House
2 beds
Apr 21 – 26
4.94 out of 5 average rating, 1139 reviews
Superhost
Yurt in Putney
~Luxury Blue Haven Yurt~
Apr 21 – 26
New place to stay