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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
17–22 Aug
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4.94 out of 5 average rating, 164 reviews
Top guest favourite
Home in Middlebury
New England Charm!
1 bedroom, 1 bed
23–28 Aug
5.0 out of 5 average rating, 20 reviews
Superhost
Room in Middlebury
Cunningham Towers
2 beds
9–14 Aug
4.82 out of 5 average rating, 39 reviews
Guest favourite
Home in Waterbury
Beautiful bunker hill home with Gym and yard!
2 bedrooms, 2 beds
6–11 Aug
4.88 out of 5 average rating, 8 reviews
Guest favourite
Holiday home in Woodbury
UNIQUE and GORGEOUS historic loft style rental
1 bedroom, 1 bed
8–13 Aug
4.87 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Southbury
Cozy Apartment Centrally Located in Southbury
1 bedroom, 2 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 103 reviews
Top guest favourite
Guest suite in Woodbury
NewEngland Apart/Woodbury Bike trail&Peaceful!
1 bedroom, 1 bed
23–28 Aug
4.98 out of 5 average rating, 41 reviews
Guest favourite
Flat in Watertown
Steele Brook Manor
2 bedrooms, 3 beds
17–22 Aug
4.94 out of 5 average rating, 51 reviews
Home in Middlebury
Lake Quassapaug Homestead
2 bedrooms, 2 beds
7–12 Aug
4.75 out of 5 average rating, 8 reviews
Guest favourite
Home in Woodbury
Ferris House: Private 19th Century Home
3 bedrooms, 4 beds
7–12 Aug
4.94 out of 5 average rating, 107 reviews
Guest favourite
Home in Bethlehem
The Parish house
3 bedrooms, 3 beds
6–11 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Middlebury
Cozy One Bedroom Apartment in Middlebury, CT
1 bedroom, 2 queen beds
15–20 Sept
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Barn in Roxbury
Fully Renovated Rural Barn
1 bedroom, 2 beds
23–28 Aug
5.0 out of 5 average rating, 106 reviews
Top guest favourite
Guest house in Newtown
Guest Suite at Wisteria Gardens
1 bedroom, 1 queen bed
22–27 Aug
4.99 out of 5 average rating, 175 reviews
Superhost
Flat in Waterbury
Home away from home
2 bedrooms, 2 queen beds
13–18 Aug
4.92 out of 5 average rating, 107 reviews
Hotel room in Southbury
Wyndham Southbury | King | Near I-84
1 bedroom, 1 king bed
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Southbury
The Cottage at Cedar Spring Farm
1 bedroom, 1 queen bed
16–21 Aug
4.98 out of 5 average rating, 170 reviews
Guest favourite
Home in Waterbury
Come and enjoy the BURY's of CT!
2 bedrooms, 4 beds
20–25 Sept
4.95 out of 5 average rating, 105 reviews
Top guest favourite
Guest house in Southbury
The Perch in the Purchase
1 bedroom, 2 beds
20–25 Sept
5.0 out of 5 average rating, 71 reviews