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, 167 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 13
Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.95 out of 5 average rating, 196 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 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 6
Rooms in Northfield
Deerfield King Suite at Centennial House B&B
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
New place to stay
Photo 1 of 29
Guest favourite
Cottage in Chesterfield
Modern Luxury on the Lake
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 6 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 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 6
Room in Northfield
Sturbridge Queen Room at Centennial House B&B
1 queen bed, 1 bathroom
25–30 Oct
New place to stay
Photo 1 of 6
Guest favourite
Room in Chesterfield
Waterfront Paradise - 1.3 mile to Brattleboro
2 beds, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 69 reviews
Photo 1 of 28
Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds, 4 bathrooms
12–17 Oct
New place to stay
Photo 1 of 29
Top 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 14
Guest favourite
Cottage in Chesterfield
Tiny Cottage on Spofford Lake
1 bedroom, 1 queen bed, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 11 reviews
Photo 1 of 16
Top guest favourite
Place to stay in Chesterfield
The Ultimate Romantic Getaway
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 67 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, 105 reviews
Photo 1 of 29
Top guest favourite
Guest suite in Jaffrey
Comfy Quarters Suite 1
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 380 reviews