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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
,
4.94 out of 5 average rating, 164 reviews
Superhost
Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
9–14 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
5–10 Aug
4.88 out of 5 average rating, 8 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
Top guest favourite
Guest suite in Woodbury
NewEngland Apart/Woodbury Bike trail&Peaceful!
1 bedroom, 1 bed, 1 bathroom
23–28 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, 103 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, 51 reviews
Home in Middlebury
Lake Quassapaug Homestead
2 bedrooms, 2 beds, 1 bathroom
6–11 Aug
4.75 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
15–20 Sept
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Woodbury
Ferris House: Private 19th Century Home
3 bedrooms, 4 beds, 1.5 bathrooms
6–11 Aug
4.94 out of 5 average rating, 107 reviews
Hotel room in Southbury
Wyndham Southbury | King | Near I-84
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 3 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
Home in Cheshire
The Ideal Connecticut Getaway.
4 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest house in Southbury
The Nest. Large studio in the Woods.
1 bedroom, 1 queen bed, 1 bathroom
6–11 Aug
4.94 out of 5 average rating, 93 reviews
Home in Watertown
Historic Litchfield County Home
5 bedrooms, 6 beds, 3.5 bathrooms
17–22 Aug
4.88 out of 5 average rating, 32 reviews
Guest favourite
Home in Bethlehem
The Parish house
3 bedrooms, 3 beds, 1 bathroom
5–10 Aug
5.0 out of 5 average rating, 6 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
Top guest favourite
Guest house in Newtown
Guest Suite at Wisteria Gardens
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.99 out of 5 average rating, 175 reviews