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Middlebury vacation rentals

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Top-rated vacation rentals in Middlebury

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Home in Middlebury
HOT TUB|BeauitifulBackyardOasis|NewlyRenovated|
HOT TUB!! There's a brand new hot tub on this property that is ready for unlimited fun!! This newly/fully renovated 3 bedroom / 2 bathroom ranch house in the heart of Amish country is ready for you to explore the abundant activities in northern Indiana. It is the perfect place for your stay in Middlebury and Shipshewana no matter what the purpose of travel is! It's in a very quiet neighborhood and close to everything in town. Enjoy the backyard oasis for a nice relaxing time: hot tub, seating, fire pit (firewood provided), and backyard games. Or if you want to get out and explore, it's less than 5 minutes away from the famous Das Dutchman Essenhaus restaurant; 15 minutes from world-renowned Shipshewana where there are shops, restaurants, the well known Flea Market, and Blue Gate Theatre; 10 minutes to the Bonneyville Mill Park where you can watch the old fashioned grinding and enjoy hiking and lover scenery. The Pumpkinvine Trails is only about 1 mile away where you can take a relaxing walk/bike ride through the countryside. Nappanee has additional Amish culture with shopping, theatre, and dining. All this and more as you relax and enjoy this wonderful area full of culture and hospitality. In this updated property, we aim to make your stay a relaxing one, whether for vacation, business, travel, or a sporting event.
$124 per night
Farm stay in Middlebury
Mini Farm in Amish Country near Pumpkinvine Trail
Come visit the heart of Amish country and experience peaceful quiet country living. The guesthouse gives you views of beautiful sunrises and amazing sunsets. You can watch our animals grazing and playing in the field. Our animals will more than likely meet you at the fence hoping for a treat (available upon request). We are located 1/4 mile from one of the Pumpkinvine Nature Trail entry points. We have a variety of bikes from kids to adult available for rent. ***No pets allowed!
$122 per night
Rental unit in Middlebury
Berry's Nest with Hot Tub
Kick back and relax in this calm, stylish space located downtown in the historical Middlebury Indiana. You can stay in and soak in the hot tub or visit the local shops nearby like Joyfully Said Home and the Mustard Seed Marketplace, and grab a slice of pizza or a scoop of ice cream at Danny's Diner. Conveniently located only 10 minutes from down town Shipshewana and the flea market!
$152 per night

Stay near Middlebury's top sights

Photo of Das Dutchman Essenhaus
Das Dutchman Essenhaus43 locals recommend
Photo of Rulli's Italian Rest Inc
Rulli's Italian Rest Inc3 locals recommend
Photo of 41 Degrees North Restaurant and Bar
41 Degrees North Restaurant and Bar10 locals recommend
Photo of Harding's Friendly Market
Harding's Friendly Market5 locals recommend
Photo of Krider "World’s Fair" Garden
Krider "World’s Fair" Garden11 locals recommend
Photo of West on Warren Gallery + Grill
West on Warren Gallery + Grill10 locals recommend

Other great vacation rentals in Middlebury

Rental unit in Middlebury
RV's, Amish, and Notre Dame, Oh My!
$99 per night
Private room in Goshen
The Granary at the Ol' Barn
$44 per night
Home in Middlebury
FarmCountry|Amish Country|NewlyRenovated|
$89 per night
Rental unit in Middlebury
⭐ Peaceful apt in the country-close to Shipshewana
$90 per night
Cabin in Shipshewana
Log Cabin
$111 per night
Private room in Shipshewana
Picket Fence Farm Getaway Retreat Suite
$41 per night
Home in Middlebury
Serenity Farmhouse in Indiana Amish Country
$149 per night
Rental unit in Goshen
Wildwood at the Ol' Barn
$90 per night
Loft in Shipshewana
Hidden Country Hide-A-Way
$61 per night
Home in Middlebury
Spruce House - cozy, spacious and charming home.
$156 per night
Rental unit in Goshen
Half-Moon Cottage
$75 per night
Rental unit in Goshen
Charming and Cozy
$50 per night
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