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Search results; Over 1,000 homes in Middlebury

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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
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Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
1–6 Sept
4.83 out of 5 average rating, 41 reviews
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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
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Guest favourite
Home in Watertown
Historic Litchfield County Home
5 bedrooms, 6 beds, 3.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 33 reviews
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Guest favourite
Home in Woodbury
Ferris House: Private 19th Century Home
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Sept
4.94 out of 5 average rating, 107 reviews
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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
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Superhost
Home in Southbury
Cozy Nature Retreat at Chateau Madeux
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 67 reviews
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Home in Woodbury
Nature & Luxury @Lavender Lake Est (Kosher option)
6 bedrooms, 11 beds, 5.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 24 reviews
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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
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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
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Top guest favourite
Guest suite in Watertown
Private King suite w/ separate entry-Walk to Taft!
1 bedroom, 2 beds, 1 bathroom
3–8 Sept
4.98 out of 5 average rating, 102 reviews
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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, 13 reviews
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Hotel room in Southbury
Wyndham Southbury | 2 Queen | On-Site Bar
1 bedroom, 2 queen beds, 1 bathroom
1–6 Sept
New place to stay
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Top guest favourite
Room in Naugatuck
Cozy semi-basement studio (independent access)
1 bed, 1 bathroom
28 Sept – 3 Oct
4.95 out of 5 average rating, 74 reviews
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Guest favourite
Guest house in Watertown
Private studio guesthouse
1 queen bed, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 122 reviews
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Guest favourite
Home in Waterbury
Ideal for sightseeing or long stays.
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.83 out of 5 average rating, 12 reviews
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Guest suite in Southbury
Watch Hill Hideaway - Unit B
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.74 out of 5 average rating, 65 reviews
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Top guest favourite
Flat in Southbury
Cozy Apartment Centrally Located in Southbury
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 109 reviews
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Guest favourite
Flat in Southbury
Southbury Charming Studio on Beautiful Grounds
2 beds, 1 bathroom
21–26 Sept
4.91 out of 5 average rating, 11 reviews