Holiday rentals in Middlebury

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Top-rated holiday rentals in Middlebury

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

Guest favourite

Guest suite in Shipshewana

4.98 out of 5 average rating, 100 reviews

Cozy Industrial Farmhouse Walkout Basement

A newly renovated basement guest suite in the heart of Amish Country. Enjoy playing pool and a 60"TV during your stay. 1 mile from town and 34 miles from Notre Dame stadium. Enjoy a morning walk around the block and campfire in the evening. Playset and in-ground trampoline. Private entrance. One queen bed with futon and/or air mattress. Living room with smart TV, WiFi, cozy elec. fireplace, AC, elec. heat. Kitchenette with fridge, microwave, coffee maker /griddle /toaster oven. (No kitchen sink)

30 Oct – 6 Nov

£108 per night
Guest favourite

Flat in Goshen

4.96 out of 5 average rating, 728 reviews

Half-Moon Cottage

Enjoy privacy in this beautifully handcrafted cottage with arched ceilings. The cottage is 2 miles from downtown Goshen - a vibrant small town with restaurants and shops. It's 1 mile from Goshen College, 45 minutes from Notre Dame and 25 minutes from the Amish town of Shipshewana. The cottage is beside a fruit, nut and berry orchard and gardens. It's adjacent to a city bike trail that links to the Pumpkinvine nature/bike trail. It's close to a train crossing (with whistle) and a busy street.

29 Dec – 5 Jan

£74 per night
Guest favourite

Home in Shipshewana

4.94 out of 5 average rating, 377 reviews

Davis Street in Shipshewana

Davis Street in Shipshewana, located in the heart of Shipshewana Indiana's Amish country. Very close to the Auction & Flea Market, and within walking distance to local theatre, shops and restaurants. We offer cozy and friendly accommodations for the perfect country getaway. A perfect place to relax and enjoy partaking of the local small town pleasures. Access to the Pumpkinvine Nature Hiking/Biking trail is just 1 mile. And just 40 miles from Notre Dame/South Bend. (for the Irish football fans)

16–23 Sept

£102 per night

Popular amenities for Middlebury holiday rentals

Stay near Middlebury's top sights

Das Dutchman Essenhaus43 locals recommend
Rulli's Italian Rest Inc3 locals recommend
Essenhaus Inn & Conference Center6 locals recommend
41 Degrees North Restaurant and Bar10 locals recommend
Harding's Friendly Market5 locals recommend
Krider "World’s Fair" Garden11 locals recommend

Other great holiday rentals in Middlebury

Guest favourite

Home in Middlebury

4.9 out of 5 average rating, 119 reviews

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

23–30 Aug

£279 per night
Guest favourite

Home in Shipshewana

4.96 out of 5 average rating, 253 reviews

The Oasis in Shipshewana

17–24 Sept

£147 per night
Guest favourite

Flat in Shipshewana

4.82 out of 5 average rating, 319 reviews

Basement Apartment *conveniently near Shipshewana*

8–15 Jul

£60 per night
Guest favourite

Guest suite in Goshen

4.97 out of 5 average rating, 261 reviews

Lofty Spaces, entire upper level, 5 mi from town

28 Dec – 4 Jan

£53 per night
Guest favourite

Flat in Cassopolis

4.99 out of 5 average rating, 309 reviews

The Hideaway on Mitchellii Lane

8–15 Sept

£70 per night
Superhost

Home in Goshen

4.87 out of 5 average rating, 113 reviews

Secluded, Sunny 2 bedroom Retreat in the Woods

14–21 Aug

£133 per night
Guest favourite

Guest suite in Sturgis

4.97 out of 5 average rating, 188 reviews

"Hawthorne Place - beautiful inside and out"

7–14 Apr

£61 per night
Guest favourite

Flat in Shipshewana

5.0 out of 5 average rating, 257 reviews

Hidden Creek

26 Oct – 2 Nov

£157 per night
Guest favourite

Flat in Elkhart

4.97 out of 5 average rating, 408 reviews

Whispering Pines

6–13 Oct

£83 per night
Superhost

Flat in Middlebury

4.92 out of 5 average rating, 48 reviews

Berry's Nest with Hot Tub

30 Jul – 6 Aug

£114 per night
Guest favourite

Farm stay in Middlebury

5.0 out of 5 average rating, 54 reviews

Farm Stay in Amish Country - 2 Bedroom 1 Bath

3–10 Sept

£148 per night
Guest favourite

Loft in Shipshewana

4.98 out of 5 average rating, 96 reviews

Hidden Country Hide-A-Way

4–11 Feb

£84 per night

Quick stats about holiday rentals in Middlebury

Total rentals

10 properties

Popular amenities

Lake access, Gym and BBQ grill

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

760 reviews

Nightly prices starting at

£32 before taxes and fees

Destinations to explore

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