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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
30 Sept – 5 Oct
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5.0 out of 5 average rating, 20 reviews
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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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Home in Waterbury
Beautiful bunker hill home with Gym and yard!
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
4.9 out of 5 average rating, 10 reviews
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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, 166 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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Flat in Watertown
Steele Brook Manor
2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
4.94 out of 5 average rating, 54 reviews
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Home in Middlebury
Lake Quassapaug Homestead
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
4.75 out of 5 average rating, 8 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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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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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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Flat in Waterbury
Home away from home
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 111 reviews
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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
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Home in Watertown
Cozy Cottage
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.77 out of 5 average rating, 90 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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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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Top guest favourite
Home in Wolcott
Peaceful 2BR Retreat Near Bristol & Waterbury
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Sept
4.96 out of 5 average rating, 26 reviews
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Top guest favourite
Cottage in Woodbury
The serenity farm cottage
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.89 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Woodbury
Your Perfectly Wonderful Woodbury Sanctuary!
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Jan
4.99 out of 5 average rating, 147 reviews
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Home in Oxford
Lakefront Summer Oasis - kayak, fish and get cozy!
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 78 reviews