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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
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
Guest favourite
Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
8–13 Sept
4.83 out of 5 average rating, 42 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 Watertown
Historic Litchfield County Home
5 bedrooms, 6 beds, 3.5 bathrooms
7–12 Sept
4.88 out of 5 average rating, 33 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
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
Featured hotel
Room in Southbury
Double room
2 double beds, 1 bathroom
5–10 Sept
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, 105 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
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
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
Superhost
Flat in Waterbury
Cozy 1b/1b beautiful views Hopeville Wtby 2nd Flr
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 49 reviews
Guest favourite
Guest house in Watertown
Private studio guesthouse
1 queen bed, 1 bathroom
12–17 Sept
4.93 out of 5 average rating, 123 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
Guest favourite
Flat in Waterbury
Home away from home
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 111 reviews
Guest favourite
Flat in Southbury
Southbury Charming Studio on Beautiful Grounds
2 beds, 1 bathroom
21–26 Sept
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Home in Waterbury
entire home, pet friendly
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 141 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