filters

Search results; Over 1,000 homes in Winchester

Guest favourite
Cabin in Winchester
Lakeside rustic seasonal cottage
2 bedrooms, 3 beds, 1 private bathroom
13–18 Sept
,
4.83 out of 5 average rating, 36 reviews
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 9 reviews
Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 bathrooms
30 Oct – 4 Nov
4.85 out of 5 average rating, 165 reviews
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.83 out of 5 average rating, 60 reviews
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Rooms in Hinsdale
Country Retreat
2 bedrooms, 3 queen beds, 1 bathroom
4–9 Jun
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Cabin in Guilford
Cozy Loft Cabin in Vermont with Sauna
3 bedrooms, 7 beds, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Brattleboro
Bright, spacious country home
4 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.91 out of 5 average rating, 65 reviews
Home in Athol
The Rafors Lake House
4 bedrooms, 7 queen beds, 3.5 bathrooms
2–7 Sept
New place to stay
Top guest favourite
Cottage in Brattleboro
Forest Street Retreat Attached Guest House
2 bedrooms, 2 queen beds, 1 bathroom
29 Oct – 3 Nov
4.99 out of 5 average rating, 146 reviews
Guest favourite
Home in Marlborough
4 BR Monadnock View Luxury Chalet
4 bedrooms, 5 beds, 5.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Northfield
Cozy Home with Relaxing Views
3 bedrooms, 3 beds, 1.5 bathrooms
15–22 Sept
4.88 out of 5 average rating, 32 reviews
Campsite in Winchester
Escape to our serene RV pad in Winchester, NH
1 bedroom, 1 bed, 1 bathroom
2–7 Sept
Top guest favourite
Flat in Brattleboro
Charming 2BR Vermont Home • Porch • Full Kitchen
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.93 out of 5 average rating, 88 reviews
Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
2–7 Sept
4.98 out of 5 average rating, 46 reviews
Guest favourite
Flat in Greenfield
Treetop Haven
2 bedrooms, 3 beds, 1 bathroom
28 Oct – 2 Nov
4.91 out of 5 average rating, 45 reviews
Top guest favourite
Home in Keene
The Brick House on Washington Street
3 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.93 out of 5 average rating, 249 reviews
Guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 12 reviews