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Search results; Over 1,000 homes in Middlebury

Top guest favorite
Home in Middlebury
Remodeled open-concept home near downtown
3 bedrooms, 5 beds, 2.5 private baths
Aug 15 – 20
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4.97 out of 5 average rating, 124 reviews
Top guest favorite
Cottage in Middlebury
Walk to Main Street with private parking
4.92 out of 5 average rating, 156 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 27 – Oct 2
Top guest favorite
Apartment in Middlebury
Mountain views from skylights, near trails
4.93 out of 5 average rating, 76 reviews, 1 bedroom, 1 bed, 1 bath
Aug 23 – 28
Top guest favorite
Room in Middlebury
Victorian suite near Middlebury College
4.91 out of 5 average rating, 422 reviews, 1 king bed, 1 bath
Aug 16 – 21
Guest favorite
Apartment in Middlebury
New England home with a fire pit
4.97 out of 5 average rating, 146 reviews, 3 bedrooms, 4 beds, 2 baths
Oct 4 – 9
Top guest favorite
Home in Middlebury
Quiet bungalow 1 mile from Middlebury College
5.0 out of 5 average rating, 18 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 13 – 18
Top guest favorite
Home in Middlebury
Renovated with a fire ring and grill
4.98 out of 5 average rating, 211 reviews, 2 bedrooms, 5 beds, 1.5 baths
Aug 16 – 21
Top guest favorite
Guesthouse in Middlebury
1800s brick farmhouse in a tranquil valley
4.88 out of 5 average rating, 160 reviews, 4 bedrooms, 6 beds, 1.5 baths
Aug 14 – 19
Top guest favorite
Guest suite in Weybridge
Riverfront fire pit near Middlebury College
4.98 out of 5 average rating, 486 reviews, 1 bedroom, 1 bed, 1 bath
Oct 18 – 23
Top guest favorite
Apartment in New Haven
Mountain views from a 25-acre property
4.98 out of 5 average rating, 245 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 15 – 20
Top guest favorite
Home in Middlebury
At the foot of the Green Mountains
4.99 out of 5 average rating, 524 reviews, 1 bedroom, 1 bed, 1 bath
Oct 18 – 23
Top guest favorite
Home in Middlebury
Walk to downtown and Middlebury College
4.91 out of 5 average rating, 102 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
Guest favorite
Home in Middlebury
Fireplace, fire pit, and walkable downtown
4.96 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 13 – 18
Top guest favorite
Apartment in Middlebury
High ceilings, skylights, and mountain views
4.99 out of 5 average rating, 186 reviews, 1 bedroom, 2 beds, 1 bath
Oct 19 – 24
Home in Middlebury
New England chalet next to Middlebury College
4 bedrooms, 4 beds, 2 baths
Aug 16 – 21
Top guest favorite
Home in Middlebury
3-story log home near Middlebury College
4.94 out of 5 average rating, 80 reviews, 4 bedrooms, 6 beds, 2 baths
Aug 31 – Sep 5
Guest favorite
Home in Middlebury
Central Middlebury home with EV charger
4.88 out of 5 average rating, 17 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 15 – 20
Top guest favorite
Home in Middlebury
Renovated with a fireplace, near Waybury Inn
5.0 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 18 – 23
Top guest favorite
Apartment in Middlebury
Waterfall views from a historic 1700s building
4.95 out of 5 average rating, 82 reviews, 1 bedroom, 1 bed, 1 bath
Dec 17 – 22