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Search results; Over 1,000 homes in Dudley

Superhost
Cottage in Dudley
Cozy, 3BR lake-side retreat and outdoor oasis
3 bedrooms, 3 beds, 2 private bathrooms
3–10 Oct
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4.85 out of 5 average rating, 54 reviews
Superhost
Guest suite in Charlton
Baker Pond Hideaway
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
4.85 out of 5 average rating, 441 reviews
Guest favourite
Home in Webster
Point Pleasant - Mumford Cove
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.9 out of 5 average rating, 48 reviews
Superhost
Home in Webster
Family-Friendly 3-BR Cozy Webster Home w/Balcony
3 bedrooms, 6 beds, 1 bathroom
5–10 Sept
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Home in Webster
The Big Lake Life
3 bedrooms, 11 beds, 3 bathrooms
19–25 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Woodstock
The Lakehouse Haven – Sunset views & Relaxation
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Flat in Dudley
웃❤️유 PRIVATE STUDIO - SAFE GORGEOUS HIDEOUT
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.82 out of 5 average rating, 572 reviews
Guest favourite
Flat in Dudley
Cozy Family Apartment
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.85 out of 5 average rating, 59 reviews
Guest favourite
Guest house in Thompson
Cute Connecticut Cottage
4 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Webster
Webster MA on the Lake 1 Bedroom.
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 56 reviews
Guest favourite
Home in Webster
Family-friendly 5-BR Cozy Webster Home w/ Balcony
5 bedrooms, 8 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Woodstock
Cedar Ridge: House
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 277 reviews
Guest favourite
Cottage in Webster
The Heron Cottage on Webster Lake!
2 bedrooms, 4 beds, 1 bathroom
8–14 Sept
4.93 out of 5 average rating, 27 reviews
Guest favourite
Home in Thompson
Dock & Sunset Views! Waterfront Thompson Getaway
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Webster
Webster Lake - One Home / Two Apartments
4 bedrooms, 6 beds, 3 bathrooms
5–10 Sept
4.93 out of 5 average rating, 40 reviews
Guest favourite
Home in Webster
Fully Renovated Waterfront Lake House w/ Docks
3 bedrooms, 5 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Woodstock
Secluded 2 Acre Lake Front Home!
4 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.85 out of 5 average rating, 139 reviews
Guest favourite
Treehouse in Thompson
The Tree House at Underhill Hollow
2 bedrooms, 2 beds, 1.5 bathrooms
26 Sept – 1 Oct
4.96 out of 5 average rating, 449 reviews
Top guest favourite
Home in Brimfield
Cozy Log Cabin | Lake Access, Kayaks & Brook
3 bedrooms, 4 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 16 reviews