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Search results; Over 1,000 homes in Middlebury

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Top 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, 170 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
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, 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
1–6 Oct
4.98 out of 5 average rating, 42 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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Guest favourite
Room in Middlebury
Cunningham Towers
2 beds, 1 bathroom
1–6 Oct
4.84 out of 5 average rating, 43 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
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Featured hotel
Hotel in Southbury
Heritage Hotel Golf & Conference Center, Double r.
1 bedroom, 2 double beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 3 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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Guest suite in Middlebury
Country Retreat Near Lake Quassapaug
1 bedroom, 3 beds, 1 bathroom
1–8 Oct
4.9 out of 5 average rating, 49 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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Guest suite in Southbury
Watch Hill Hideaway - Unit B
2 bedrooms, 3 beds, 1 bathroom
2–7 Oct
4.74 out of 5 average rating, 66 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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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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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, 115 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 suite in Southbury
Charming Historic Tavern Suite
1 bedroom, 1 queen bed, 2 bathrooms
3–8 Oct
4.89 out of 5 average rating, 57 reviews
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Guest favourite
Cabin in Woodbury
Cozy Cabin By The Brook One
1 bedroom, 1 double bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 7 reviews
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Superhost
Guest suite in Waterbury
Private cozy getaway
1 bedroom, 3 beds, 1 bathroom
25–30 Oct
4.88 out of 5 average rating, 177 reviews