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Search results; Over 1,000 homes in Dudley

Superhost
Flat in Dudley
웃❤️유 PRIVATE STUDIO - SAFE GORGEOUS HIDEOUT
1 bedroom, 2 beds, 1 private bathroom
13–18 Sept
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4.82 out of 5 average rating, 573 reviews
Superhost
Cottage in Dudley
Cozy, 3BR lake-side retreat and outdoor oasis
3 bedrooms, 3 beds, 2 bathrooms
3–10 Oct
4.85 out of 5 average rating, 54 reviews
Guest favourite
Guest suite in Charlton
Baker Pond Hideaway
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
4.85 out of 5 average rating, 442 reviews
Guest favourite
Flat in Dudley
Cozy Family Apartment
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.85 out of 5 average rating, 61 reviews
Guest favourite
Home in Webster
Point Pleasant - Mumford Cove
4 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.9 out of 5 average rating, 48 reviews
Top guest favourite
Farm stay in Sutton
Stevenson Farm / Way Back Home
6 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 53 reviews
Guest favourite
Home in Woodstock
Cedar Ridge: House
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.92 out of 5 average rating, 278 reviews
Top guest favourite
Home in Woodstock
The Lakehouse Haven – Sunset views & Relaxation
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 16 reviews
Top 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, 9 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
Superhost
Home in Webster
Family-Friendly 3-BR Cozy Webster Home w/Balcony
3 bedrooms, 6 beds, 1 bathroom
10–15 Sept
4.86 out of 5 average rating, 7 reviews
Guest favourite
Home in Southbridge
Charming Cape--Kid & Dog Friendly 🐾
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
4.93 out of 5 average rating, 429 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
Guest favourite
Home in Webster
Family-friendly 5-BR Cozy Webster Home w/ Balcony
5 bedrooms, 8 beds, 1 bathroom
31 Dec – 5 Jan
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Webster
Webster Lake - One Home / Two Apartments
4 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
4.93 out of 5 average rating, 40 reviews
Home in Thompson
Direct Lakefront Retreat | Indian Ranch | Casinos
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
Top guest favourite
Guest suite in Thompson
Trees, pond, and wildlife in its entire splendor
3 bedrooms, 5 beds, 2 bathrooms
22–27 Sept
4.96 out of 5 average rating, 81 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, 57 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