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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
Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
20–25 Sept
4.83 out of 5 average rating, 42 reviews
Featured hotel
Room in Southbury
Double room
2 double beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 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
Top guest favourite
Flat in Middlebury
Cozy Apartment with Water View of Brook
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 169 reviews
Guest favourite
Home in Watertown
Historic Litchfield County Home
5 bedrooms, 6 beds, 3.5 bathrooms
22–27 Sept
4.88 out of 5 average rating, 33 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
Guest favourite
Home in Woodbury
Ferris House: Private 19th Century Home
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 107 reviews
Top guest favourite
Cabin in Woodbury
The Cozy Cabin By The Brook
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Waterbury
Ideal for sightseeing or long stays.
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 14 reviews
Superhost
Home in Southbury
Cozy Nature Retreat at Chateau Madeux
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Sept
4.88 out of 5 average rating, 68 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
Home in Woodbury
Nature & Luxury @Lavender Lake Est (Kosher option)
6 bedrooms, 11 beds, 5.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Southbury
Cozy Connecticut getaway!
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 37 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
Home in Woodbury
Family-Friendly Woodbury Home with Yard + Deck!
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Nov
4.9 out of 5 average rating, 78 reviews
Guest favourite
Home in Bethlehem
Nature’s Nest: Cozy Woodland Escape for Friends
3 bedrooms, 3 beds, 2.5 bathrooms
14–19 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Flat in Waterbury
KG Comfortable living.
2 bedrooms, 2 beds, 1 bathroom
12–17 Oct
4.86 out of 5 average rating, 79 reviews
Guest favourite
Guest house in Watertown
Private studio guesthouse
1 queen bed, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 123 reviews