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Search results; 422 homes in Middlebury

Top guest favourite
Cabin in Middlebury
Cabin off 39 - Peaceful, private one bedroom cabin
1 bedroom, 1 bed, 1 private bathroom
7–12 Nov
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4.99 out of 5 average rating, 451 reviews
Top guest favourite
Home in Middlebury
Joy House on Main Luxe - Downtown Middlebury
4 bedrooms, 5 beds
12–17 Oct
4.98 out of 5 average rating, 97 reviews
Guest favourite
Home in Middlebury
Cozy 3 bedroom home in Middlebury
3 bedrooms, 3 beds
21–26 Sept
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Middlebury
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
3 bedrooms, 3 beds
21–26 Sept
4.92 out of 5 average rating, 239 reviews
Top guest favourite
Guest suite in Middlebury
Mullet's Speed Shop
1 bedroom, 2 beds
13–18 Sept
5.0 out of 5 average rating, 173 reviews
Guest favourite
Home in Middlebury
Mayberry on 8 In Amish Country Sleeps 12+
4 bedrooms, 6 beds
13–18 Sept
4.9 out of 5 average rating, 282 reviews
Top guest favourite
Cottage in Middlebury
Stone Lake Cottage Middlebury IN Boat Fish getaway
3 bedrooms, 5 beds
13–18 Sept
4.83 out of 5 average rating, 339 reviews
Guest favourite
Home in Middlebury
| Amish Country Getaway | Farm Views | Fire Pit |
3 bedrooms, 5 beds
19–24 Sept
4.94 out of 5 average rating, 35 reviews
Guest favourite
Home in Middlebury
Middlebury Getaway with In Ground Pool/Hot Tub
5 bedrooms, 2 bunk beds
3–8 Oct
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Middlebury
The Cozy Cottage on Main Street
3 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Middlebury
The Red Thread Retreat
2 bedrooms, 5 beds
25–30 Sept
4.97 out of 5 average rating, 63 reviews
Superhost
Home in Middlebury
8,400 Sq Ft Estate | Pool | Theater | Sleeps 23
6 bedrooms, 13 beds
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Middlebury
Berry's Nest
2 bedrooms, 5 beds
20–25 Sept
4.78 out of 5 average rating, 119 reviews
Top guest favourite
Tiny home in Middlebury
Modern Amish Country Tiny Home w/ Outdoor Shower
1 bedroom, 1 queen bed
28 Sept – 3 Oct
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Home in Middlebury
Farm stay in Amish Country - 4 Bedroom 2 Bath
4 bedrooms, 4 beds
15–20 Oct
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Home in Middlebury
Peaceful Amish Country Home | Family-Friendly
3 bedrooms, 4 beds
19–24 Sept
4.99 out of 5 average rating, 102 reviews
Guest favourite
Room in Middlebury
Ridge Run Inn - Room 3
2 beds
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Cabin in Bristol
Cozy Cabin in the Fruit Hills
3 bedrooms, 4 beds
11–16 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Middlebury
Rustic Roots | Middlebury Log Cabin | Shipshewana
3 bedrooms, 8 beds
20–25 Sept
4.96 out of 5 average rating, 74 reviews