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Search results; Over 1,000 homes in Middlebury

Top guest favourite
Home in Middlebury
New England Charm!
1 bedroom, 1 bed, 1 private bathroom
15–20 Sept
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5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Waterbury
Come and enjoy the BURY's of CT!
2 bedrooms, 4 beds, 1 bathroom
16–21 Oct
4.95 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Middlebury
Cozy Apartment with Water View of Brook
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 168 reviews
Top guest favourite
Home in Woodbury
Your Perfectly Wonderful Woodbury Sanctuary!
4 bedrooms, 4 beds, 2.5 bathrooms
19–24 Oct
4.99 out of 5 average rating, 147 reviews
Guest favourite
Flat in Middlebury
Cozy One Bedroom Apartment in Middlebury, CT
1 bedroom, 2 queen beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 41 reviews
Guest favourite
Home in Waterbury
Beautiful bunker hill home with Gym and yard!
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.82 out of 5 average rating, 11 reviews
Home in Middlebury
Lake Quassapaug Homestead
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.75 out of 5 average rating, 8 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
Guest favourite
Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
9–14 Sept
4.83 out of 5 average rating, 42 reviews
Guest favourite
Home in Bethlehem
The Parish house
3 bedrooms, 3 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Woodbury
Ferris House: Private 19th Century Home
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.94 out of 5 average rating, 107 reviews
Featured hotel
Room in Southbury
Double room
2 double beds, 1 bathroom
6–11 Sept
Top guest favourite
Home in Waterbury
Amazing views of the Brass City
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Oct
4.96 out of 5 average rating, 160 reviews
Guest favourite
Home in Waterbury
Ideal for sightseeing or long stays.
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.85 out of 5 average rating, 13 reviews
Home in Watertown
Cozy Cottage
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.77 out of 5 average rating, 90 reviews
Guest favourite
Home in Watertown
Historic Litchfield County Home
5 bedrooms, 6 beds, 3.5 bathrooms
8–13 Sept
4.88 out of 5 average rating, 33 reviews
Top guest favourite
Home in Wolcott
Peaceful 2BR Retreat Near Bristol & Waterbury
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Cheshire
The Ideal Connecticut Getaway.
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Flat in Waterbury
Comfortable 2BR Home in Waterbury, CT
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.8 out of 5 average rating, 5 reviews