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Search results; 605 homes in Middlebury

Top guest favourite
Cottage in Middlebury
Stone Lake Cottage Middlebury IN Boat Fish getaway
3 bedrooms, 5 beds, 4 private bathrooms
8–13 Oct
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4.83 out of 5 average rating, 332 reviews
Top guest favourite
Home in Middlebury
Joy House on Main Luxe - Downtown Middlebury
4.98 out of 5 average rating, 85 reviews, 4 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
Guest favourite
Home in Middlebury
Cozy 3 bedroom home in Middlebury
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 1 bathroom
1–6 Jul
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Home in Middlebury
| Amish Country Getaway | Farm Views | Fire Pit |
5.0 out of 5 average rating, 27 reviews, 3 bedrooms, 5 beds, 1 bathroom
4–9 Jul
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Cabin in Middlebury
Ridge Run Inn - Full Cabin
5.0 out of 5 average rating, 39 reviews, 4 bedrooms, 8 beds, 4.5 bathrooms
15–20 Aug
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Cabin in Middlebury
Cabin off 39 - Peaceful, private one bedroom cabin
4.99 out of 5 average rating, 433 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Sept
Guest favourite
Home in Middlebury
Mayberry on 8 In Amish Country Sleeps 12+
4.9 out of 5 average rating, 271 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Middlebury
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
4.93 out of 5 average rating, 227 reviews, 3 bedrooms, 3 beds, 2 bathrooms
28 Jul – 2 Aug
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Home in Middlebury
Farm stay in Amish Country - 4 Bedroom 2 Bath
5.0 out of 5 average rating, 94 reviews, 4 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
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Guest suite in Middlebury
Mullet's Speed Shop
5.0 out of 5 average rating, 145 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Home in Middlebury
The Red Thread Retreat
4.96 out of 5 average rating, 55 reviews, 2 bedrooms, 5 beds, 2 bathrooms
5–10 Aug
Top guest favourite
Home in Middlebury
The Cozy Cottage on Main Street
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 6 beds, 2 bathrooms
6–11 Jul
Guest favourite
Home in Shipshewana
Little Red Hen *NEW* in 2024
4.88 out of 5 average rating, 81 reviews, 3 bedrooms, 5 beds, 1 bathroom
3–8 Jul
Top guest favourite
Home in Shipshewana
Newly Renovated Home-Comfort in Quiet Shipshewana
5.0 out of 5 average rating, 84 reviews, 2 bedrooms, 4 beds, 1 bathroom
26–31 Jul
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Home in Shipshewana
The Frey House
4.96 out of 5 average rating, 113 reviews, 5 bedrooms, 7 beds, 3 bathrooms
29 Aug – 3 Sept
Top guest favourite
Camper van/Motorhome in Middlebury
1-bedroom RV, in a quiet spot for couples getaway
4.96 out of 5 average rating, 143 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Jul
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Guest suite in Shipshewana
Picket Fence Farm Private Guest Retreat Suite
4.97 out of 5 average rating, 602 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Cabin in Middlebury
Rustic Roots Cabin| 3bd/3ba Cozy/Shipshewana/ND
4.95 out of 5 average rating, 63 reviews, 3 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
Guest favourite
Farm stay in Shipshewana
Family Farm Stay+Buggy & Pony Rides + Firepit
4.97 out of 5 average rating, 34 reviews, 1 bedroom, 2 beds, 1 bathroom
14–19 Jul