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Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

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

⭐ Private, spacious apartment in the country
Entire apartment · 4 guests · 2 beds · 1 bath

⭐ Private, spacious apartment in the countryNestled in the quiet countryside between Middlebury and Shipshewana, our spacious, private apartment is the perfect place to call “home” for your next getaway to Amish country. This newly painted and furnished apartment is ideal for you to relax and recharge during your stay. We offer a fully furnished kitchen, including a sink, refrigerator, stove/oven and microwave. Whether you plan to stay in and cook, order in or eat out you will love the options this space offers.

Circle J Bed & Breakfast
SUPERHOST
Tiny house · 4 guests · 2 beds · 1 bath

Circle J Bed & BreakfastWe are located on Circle J Horse Farm, a beautiful country cabin with rustic decor, quite and cozy with all the amenities of home. For a romantic couples retreat or a family vacation.

Charming and Cozy
SUPERHOST
Entire apartment · 3 guests · 2 beds · 1 bath

Charming and CozyQuaint, charming and comfy studio apartment within a Victorian home located in the historical section of town. Separate/private entrance with stairs going to the 2nd floor. Walking distance to downtown area for shopping, restaurants, local coffee house and local brewery. Only 30 miles from Notre Dame!

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Middlebury vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Middlebury

SUPERHOST
  1. Entire cottage
  2. Howe
Peaceful Lakefront 1960 Cottage in Amish Area
  1. Tiny house
  2. Shipshewana
Tiny House on the river
SUPERHOST
  1. Entire guest suite
  2. Goshen
Lower Level Guest Suite w/ Kitchenette
SUPERHOST
  1. Entire apartment
  2. Elkhart
Whispering Pines
SUPERHOST
  1. Entire house
  2. Shipshewana
Davis Street in Shipshewana
SUPERHOST
  1. Private room
  2. Goshen
The Granary at the Ol' Barn
  1. Entire house
  2. Middlebury
Spruce House - cozy, spacious and charming home.
SUPERHOST
  1. Entire cottage
  2. Topeka
Honeyville Cottage
SUPERHOST
  1. Entire house
  2. Goshen
The Villa Goshen (Exclusive Use/All Guest Spaces)
SUPERHOST
  1. Entire place
  2. Shipshewana
Backyard Getaway
SUPERHOST
  1. Entire apartment
  2. Middlebury
The Farm Vista
SUPERHOST
  1. Entire apartment
  2. Osceola
Silk On the Bend

Nearby destinations