filters

Search results; Over 1,000 homes in Winchester

Photo 1 of 29
Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 shared bathrooms
3–8 Nov
,
4.85 out of 5 average rating, 168 reviews
Photo 1 of 13
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.84 out of 5 average rating, 61 reviews
Photo 1 of 29
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
17–22 Oct
4.9 out of 5 average rating, 10 reviews
Photo 1 of 29
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 10 reviews
Photo 1 of 29
Superhost
Flat in Marlboro, Vermont
Shakespeare's Cherry Tree Cottage
1 bedroom, 2 queen beds, 1 bathroom
18–23 Oct
New place to stay
Photo 1 of 25
Guest favourite
Home in Northfield
Cozy Home with Relaxing Views
3 bedrooms, 3 beds, 1.5 bathrooms
1–8 Oct
4.88 out of 5 average rating, 32 reviews
Photo 1 of 12
Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds, 1 bathroom
16–21 Dec
5.0 out of 5 average rating, 6 reviews
Photo 1 of 13
Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
21–26 Oct
4.95 out of 5 average rating, 196 reviews
Photo 1 of 29
Guest favourite
Place to stay in Winchendon
Enjoy your stay in an Antique Home in a Toy Museum
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.9 out of 5 average rating, 106 reviews
Photo 1 of 17
Guest favourite
Tiny home in Chesterfield
Cozy Cottage on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
Top guest favourite
Home in Brattleboro
Forest Green Retreat
2 bedrooms, 2 king beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 6 reviews
Photo 1 of 29
Guest favourite
Home in Dummerston
Woodsy Retreat Near Skiing, Private Pool in Summer
2 bedrooms, 4 beds, 1.5 bathrooms
18–23 Oct
4.9 out of 5 average rating, 49 reviews
Photo 1 of 29
Guest favourite
Flat in Vernon
Deck, Mountain Views: Colorful Retreat in Vernon!
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.86 out of 5 average rating, 35 reviews
Photo 1 of 29
Top guest favourite
Treehouse in Putney
Treehouse Haven in Putney-All Seasons
2 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 203 reviews
Photo 1 of 29
Top guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 15 reviews
Photo 1 of 29
Home in Charlemont
3 Bedroom 2 Bath Cottage on The Brook
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
New place to stay
Photo 1 of 27
Guest favourite
Guest house in Brattleboro
Casita by the Green: Quiet, Country, close to town
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 77 reviews
Photo 1 of 29
Top guest favourite
Guest suite in Jaffrey
Comfy Quarters Suite 1
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 380 reviews
Photo 1 of 29
Top guest favourite
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - first floor
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 77 reviews