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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
Farm Country|Amish Country|Newly Renovated|
Welcome to your home away from home!! This newly/fully renovated 2 bedroom / 2 bathroom ranch house in the heart of Amish country is ready for you to explore the abundant activities in northern Indiana. This is not only a wonderful house, but the location of this property next door to a real working farm is what makes it ideal for your country getaway, where the Amish buggies will pass leisurely by the house. You can enjoy a relaxing evening by the firepit in the backyard (firewood is provided), or you can travel about. You are less than 5 minutes away from the famous Das Dutchman Essenhaus restaurant; 10 minutes from world renowned Shipshewana where there are shops, restaurants, the well known Flea Market and Blue Gate Theatre; 15 minutes to the Bonneyville Mill Park where you can watch the old fashioned grinding and enjoy hiking and lovely 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.
$96 per night
SUPERHOST
Home in Middlebury
Game Room | Pool Table | Foosball|Family Focused|
Your home away from home! Whether you're with family or friends, our basement Game Room is the perfect place to let loose and get competitive! You'll find a high-quality pool table, foosball table, and carpet ball table, plus a high table for board games and card games! This newly renovated 3 bed/1 bath ranch house is ready for your group. We are in the heart of small-town America and ready for you to explore the abundant activities in northern Indiana. It is the perfect place for your stay.
$78 per night
SUPERHOST
Farm stay in Middlebury
Mini Farm in Amish Country near Pumpkinvine Trail
Come visit the The White Barn Inn! It is nestled in the heart of Amish Country where you can slow down and relax as you watch buggies pass by, see beautiful sunrises and sunsets and 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 available for rent. ***No pets allowed!
$139 per night
SUPERHOST

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 Essenhaus Inn & Conference Center
Essenhaus Inn & Conference Center6 locals recommend

Other great vacation rentals in Middlebury

Home in Middlebury
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
$100 per night
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Rental unit in Middlebury
⭐ Peaceful apt in the country-close to Shipshewana
$102 per night
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Loft in Shipshewana
Hidden Country Hide-A-Way
$68 per night
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Private room in Goshen
The Granary at the Ol' Barn
$45 per night
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Rental unit in Middlebury
RV's, Amish, and Notre Dame, Oh My!
$99 per night
SUPERHOST
Private room in Goshen
The Loft at the Ol' Barn
$47 per night
SUPERHOST
Cabin in Shipshewana
Log Cabin
$125 per night
SUPERHOST
Guest suite in Shipshewana
Picket Fence Farm Getaway Retreat Suite
$40 per night
SUPERHOST
Rental unit in Middlebury
The Farm Vista
$101 per night
SUPERHOST
Private room in Goshen
Charming Suite SR13
$50 per night
SUPERHOST
Rental unit in Middlebury
📍Cozy, peaceful 2nd level apt-close to Toll Rd 🌟
$89 per night
SUPERHOST
Guest suite in Shipshewana
Cozy Industrial Farmhouse Walkout Basement
$98 per night
SUPERHOST

Other types of stays on Airbnb

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  2. United States
  3. Indiana
  4. Elkhart County
  5. Middlebury