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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
6–11 Sept
,
4.94 out of 5 average rating, 166 reviews
Top guest favourite
Home in Middlebury
New England Charm!
1 bedroom, 1 bed, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 20 reviews
Superhost
Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
23–28 Aug
4.83 out of 5 average rating, 41 reviews
Top guest favourite
Home in Waterbury
Beautiful bunker hill home with Gym and yard!
2 bedrooms, 2 beds, 1 bathroom
24–29 Aug
4.9 out of 5 average rating, 10 reviews
Superhost
Home in Waterbury
Ideal for sightseeing or long stays.
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.82 out of 5 average rating, 11 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, 43 reviews
Top guest favourite
Cabin in Woodbury
The Cozy Cabin By The Brook
3 bedrooms, 3 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Watertown
Steele Brook Manor
2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
4.94 out of 5 average rating, 53 reviews
Guest favourite
Barn in Roxbury
Classic Red Barn with game room and gym
2 bedrooms, 4 beds, 1.5 bathrooms
31 Aug – 5 Sept
4.93 out of 5 average rating, 60 reviews
Guest favourite
Home in Bethlehem
Nature’s Nest: Cozy Woodland Escape for Friends
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Aug
4.95 out of 5 average rating, 22 reviews
Guest favourite
Holiday home in Woodbury
UNIQUE and GORGEOUS historic loft style rental
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
4.87 out of 5 average rating, 63 reviews
Guest favourite
Home in Waterbury
Come and enjoy the BURY's of CT!
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 105 reviews
Guest favourite
Guest suite in Waterbury
Waterbury Cozy, Private In-Law Suite
1 bedroom, 1 queen bed, 1 bathroom
21–26 Aug
4.86 out of 5 average rating, 258 reviews
Guest favourite
Home in Bethlehem
Quiet Lake Retreat | Fenced Yard | Beach Access
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Oct
4.89 out of 5 average rating, 46 reviews
Top guest favourite
Guest house in Newtown
Guest Suite at Wisteria Gardens
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 182 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, 41 reviews
Home in Woodbury
Family-Friendly Woodbury Home with Yard + Deck!
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Nov
4.9 out of 5 average rating, 77 reviews
Top guest favourite
Flat in Southbury
Cozy Apartment Centrally Located in Southbury
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 107 reviews
Hotel room in Southbury
Wyndham Southbury | King | Near I-84
1 bedroom, 1 king bed, 1 bathroom
20–25 Aug
5.0 out of 5 average rating, 3 reviews