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Search results; Over 1,000 homes in Middlebury

Photo 1 of 29
Top guest favourite
Home in Middlebury
Walk Everywhere and Enjoy a Historic Vermont Home
4 bedrooms, 4 beds, 1.5 private bathrooms
21–26 Sept
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4.96 out of 5 average rating, 110 reviews
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Top guest favourite
Cottage in Middlebury
The Cottage Apartment in downtown Middlebury.
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.92 out of 5 average rating, 165 reviews
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Top guest favourite
Home in Middlebury
In the heart of Middlebury, a modern farmhouse
3 bedrooms, 3 queen beds, 1.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 175 reviews
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Top guest favourite
Flat in Middlebury
Chipman Hill Apartment.
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 81 reviews
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Guest favourite
Home in Middlebury
Midd Manor
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Middlebury
Weybridge Cottage |Steps from Middlebury College
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 18 reviews
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Home in Middlebury
Walkable Middlebury family home
5 bedrooms, 7 beds, 3 bathrooms
22–27 Nov
5.0 out of 5 average rating, 3 reviews
Photo 1 of 28
Top guest favourite
Home in Middlebury
Downtown Middlebury River House
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 39 reviews
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Top guest favourite
Room in Middlebury
Crow's Nest
1 queen bed, 1 bathroom
16–21 Nov
4.94 out of 5 average rating, 230 reviews
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Guest favourite
Home in Middlebury
Tiny Sparrow House, Luxury & Charm in Middlebury
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Flat in Middlebury
Cozy Apartment • Minutes to Middlebury
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.84 out of 5 average rating, 218 reviews
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Top guest favourite
Home in Middlebury
The Middlebury Cottage
2 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.92 out of 5 average rating, 115 reviews
Photo 1 of 13
Guest favourite
Guest suite in Middlebury
Cozy, quiet 1-bedroom apartment with fabulous view
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
4.95 out of 5 average rating, 43 reviews
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Top guest favourite
Flat in Middlebury
Bluebird Studio- Light filled and airy
1 bedroom, 2 queen beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 188 reviews
Photo 1 of 29
Top guest favourite
Home in Cornwall
Custom Home, minutes from Middlebury
3 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 121 reviews
Photo 1 of 29
Top guest favourite
Home in Middlebury
Upscale 4BR Cottage | Walk Downtown | Hot Tub
4 bedrooms, 5 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 49 reviews
Photo 1 of 29
Top guest favourite
Home in Middlebury
Quiet East Middlebury House
2 bedrooms, 2 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 55 reviews
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Guest favourite
Guest house in Middlebury
Historic Farmhouse in Middlebury
4 bedrooms, 6 beds, 1.5 bathrooms
25–30 Sept
4.87 out of 5 average rating, 162 reviews
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Guest favourite
Flat in Middlebury
Spacious Home • Near Downtown Middlebury.
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 149 reviews