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Search results; Over 1,000 homes in Middlebury

Top guest favourite
Flat in Middlebury
Cozy Apartment with Water View of Brook
1 bedroom, 1 bed, 1 private bathroom
14–19 Aug
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4.94 out of 5 average rating, 164 reviews
Superhost
Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
4–9 Aug
4.82 out of 5 average rating, 39 reviews
Top guest favourite
Home in Middlebury
New England Charm!
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Waterbury
Beautiful bunker hill home with Gym and yard!
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Middlebury
Cozy One Bedroom Apartment in Middlebury, CT
1 bedroom, 2 queen beds, 1 bathroom
3–8 Aug
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Waterbury
Come and enjoy the BURY's of CT!
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 105 reviews
Guest favourite
Flat in Watertown
Steele Brook Manor
2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
4.94 out of 5 average rating, 50 reviews
Guest favourite
Home in Woodbury
Ferris House: Private 19th Century Home
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
4.94 out of 5 average rating, 107 reviews
Top guest favourite
Guest suite in Woodbury
NewEngland Apart/Woodbury Bike trail&Peaceful!
1 bedroom, 1 bed, 1 bathroom
25–30 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Southbury
Cozy Apartment Centrally Located in Southbury
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 102 reviews
Home in Woodbury
Family-Friendly Woodbury Home with Yard + Deck!
3 bedrooms, 4 beds, 1.5 bathrooms
18–23 Aug
4.9 out of 5 average rating, 77 reviews
Guest favourite
Home in Bethlehem
Nature’s Nest: Cozy Woodland Escape for Friends
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Home in Waterbury
Amazing views of the Brass City
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.96 out of 5 average rating, 158 reviews
Top guest favourite
Guest suite in Watertown
Lrg Studio Apartment - walk to Taft
1 queen bed, 1 bathroom
11–16 Aug
4.91 out of 5 average rating, 234 reviews
Guest favourite
Holiday home in Woodbury
UNIQUE and GORGEOUS historic loft style rental
1 bedroom, 1 bed, 1 bathroom
8–13 Aug
4.87 out of 5 average rating, 62 reviews
Superhost
Guest suite in Waterbury
Private cozy getaway
1 bedroom, 3 beds, 1 bathroom
13–18 Aug
4.87 out of 5 average rating, 169 reviews
Superhost
Flat in Watertown
Taft School Watertown/Oakville
2 bedrooms, 1 single bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 26 reviews
Guest favourite
Flat in Waterbury
Private 1 bedroom apartment in central Connecticut
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 293 reviews
Home in Watertown
Historic Litchfield County Home
5 bedrooms, 6 beds, 3.5 bathrooms
25–30 Aug
4.88 out of 5 average rating, 32 reviews