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Search results; Over 1,000 homes in Woodbury

Top guest favourite
Home in Woodbury
Your Perfectly Wonderful Woodbury Sanctuary!
4 bedrooms, 4 beds, 2.5 private bathrooms
19–24 Oct
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4.99 out of 5 average rating, 147 reviews
Top guest favourite
Guest suite in Woodbury
NewEngland Apart/Woodbury Bike trail&Peaceful!
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
4.98 out of 5 average rating, 43 reviews
Home in Woodbury
Nature & Luxury @Lavender Lake Est (Kosher option)
6 bedrooms, 11 beds, 5.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 24 reviews
Home in Woodbury
Family-Friendly Woodbury Home with Yard + Deck!
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Nov
4.9 out of 5 average rating, 78 reviews
Guest favourite
Holiday home in Woodbury
UNIQUE and GORGEOUS historic loft style rental
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.87 out of 5 average rating, 63 reviews
Top guest favourite
Farm stay in Woodbury
Historic Country Getaway with Field & Garden Views
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 43 reviews
Superhost
Home in Woodbury
Renovated Connecticut Country House sleeps 14!
4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
4.91 out of 5 average rating, 58 reviews
Top guest favourite
Cottage in Woodbury
The serenity farm cottage
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.89 out of 5 average rating, 27 reviews
Guest favourite
Home in Woodbury
Ferris House: Private 19th Century Home
3 bedrooms, 4 beds, 1.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 107 reviews
Guest favourite
Cabin in Woodbury
Cozy Cabin By The Brook One
1 bedroom, 1 double bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cabin in Woodbury
The Cozy Cabin By The Brook
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 13 reviews
Home in Woodbury
2 homes in one (in-law design) w/salt water pool
3 bedrooms, 4 beds, 3.5 bathrooms
27 Jul – 1 Aug
4.69 out of 5 average rating, 42 reviews
Guest favourite
Villa in Woodbury
Luxurious Litchfield County Summer Estate
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Watertown
Historic Litchfield County Home
5 bedrooms, 6 beds, 3.5 bathrooms
7–12 Sept
4.88 out of 5 average rating, 33 reviews
Superhost
Home in Southbury
Cozy Nature Retreat at Chateau Madeux
3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Sept
4.88 out of 5 average rating, 68 reviews
Top guest favourite
Flat in Southbury
Cozy Apartment Centrally Located in Southbury
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 111 reviews
Guest favourite
Cabin in Bethlehem
Swim, fish, kayak & RELAX!
3 bedrooms, 5 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 48 reviews
Top guest favourite
Barn in Roxbury
Luxury Rural Barn
1 bedroom, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 110 reviews
Guest favourite
Flat in Watertown
Steele Brook Manor
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 55 reviews