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Search results; Over 1,000 homes in Middlebury

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Guest favourite
Flat in Middlebury
Cozy Apartment with Water View of Brook
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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4.94 out of 5 average rating, 169 reviews
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Top guest favourite
Home in Middlebury
New England Charm!
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Flat in Middlebury
Cozy One Bedroom Apartment in Middlebury, CT
1 bedroom, 2 queen beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 42 reviews
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Guest favourite
Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
1–6 Oct
4.83 out of 5 average rating, 42 reviews
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Guest favourite
Home in Waterbury
Come and enjoy the BURY's of CT!
2 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 106 reviews
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Top guest favourite
Home in Woodbury
Your Perfectly Wonderful Woodbury Sanctuary!
4 bedrooms, 4 beds, 2.5 bathrooms
28 Oct – 2 Nov
4.99 out of 5 average rating, 147 reviews
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Home in Middlebury
Lake Quassapaug Homestead
2 bedrooms, 2 beds, 1 bathroom
19–24 Oct
4.78 out of 5 average rating, 9 reviews
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Superhost
Home in Waterbury
Beautiful bunker hill home with Gym and yard!
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.75 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Wolcott
Peaceful 2BR Retreat Near Bristol & Waterbury
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 26 reviews
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Superhost
Home in Southbury
Cozy Nature Retreat at Chateau Madeux
3 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
4.88 out of 5 average rating, 68 reviews
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Guest favourite
Home in Watertown
Historic Litchfield County Home
5 bedrooms, 6 beds, 3.5 bathrooms
1–6 Oct
4.88 out of 5 average rating, 33 reviews
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Home in Woodbury
2 homes in one (in-law design) w/salt water pool
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
4.7 out of 5 average rating, 43 reviews
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Guest favourite
Flat in Waterbury
Home away from home
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
4.92 out of 5 average rating, 112 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 Oct
4.94 out of 5 average rating, 107 reviews
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Guest favourite
Home in Bethlehem
The Parish house
3 bedrooms, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Watertown
Guest House on Country Estate
3 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
4.76 out of 5 average rating, 110 reviews
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Top guest favourite
Home in Waterbury
Amazing views of the Brass City
3 bedrooms, 3 beds, 1.5 bathrooms
11–16 Oct
4.96 out of 5 average rating, 162 reviews
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Guest favourite
Home in Watertown
Cozy Cottage
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.77 out of 5 average rating, 93 reviews
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Top guest favourite
Cottage in Woodbury
The serenity farm cottage
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 28 reviews