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.

Guest favorite

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)

Dec 13 – 20

R2,192 ZAR per night
Guest favorite

Apartment 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.

Nov 4 – 11

R1,567 ZAR per night
Guest favorite

Cabin in Shipshewana

4.97 out of 5 average rating, 315 reviews

Log Cabin

Are you looking for a quiet, relaxing and peaceful place to stay? Look no further, this little cabin is all that and more! These pictures do not do the cabin justice, we have heard this from so many guests that have stayed at our cabin! You will not be disappointed with your stay at our cabin. The kitchen is equipped with a stove, microwave, refrigerator and dishwasher. A front and back porch with beautiful views to drink a cup of coffee, read a book or relax! We hope you will come stay soon!

Sep 16 – 23

R2,448 ZAR per night

Popular amenities for Middlebury vacation 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 vacation rentals in Middlebury

Guest favorite

Home in Shipshewana

4.96 out of 5 average rating, 253 reviews

The Oasis in Shipshewana

Sep 14 – 21

R2,909 ZAR per night
Guest favorite

Home in Middlebury

4.9 out of 5 average rating, 119 reviews

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

Oct 28 – Nov 4

R4,948 ZAR per night
Guest favorite

Guest suite in Goshen

4.97 out of 5 average rating, 261 reviews

Lofty Spaces, entire upper level, 5 mi from town

Dec 15 – 22

R1,131 ZAR per night
Guest favorite

Apartment in Shipshewana

4.82 out of 5 average rating, 319 reviews

Basement Apartment *conveniently near Shipshewana*

Sep 7 – 14

R1,180 ZAR per night
Superhost

Home in Goshen

4.87 out of 5 average rating, 113 reviews

Secluded, Sunny 2 bedroom Retreat in the Woods

Aug 26 – Sep 2

R2,793 ZAR per night
Guest favorite

Apartment in Cassopolis

4.99 out of 5 average rating, 309 reviews

The Hideaway on Mitchellii Lane

Jul 10 – 17

R1,694 ZAR per night
Guest favorite

Guest suite in Sturgis

4.97 out of 5 average rating, 188 reviews

"Hawthorne Place - beautiful inside and out"

Apr 12 – 19

R1,329 ZAR per night
Guest favorite

Apartment in Shipshewana

5.0 out of 5 average rating, 257 reviews

Hidden Creek

Oct 14 – 21

R3,350 ZAR per night
Guest favorite

Apartment in Elkhart

4.97 out of 5 average rating, 408 reviews

Whispering Pines

Nov 8 – 15

R1,774 ZAR per night
Superhost

Apartment in Middlebury

4.92 out of 5 average rating, 48 reviews

Berry's Nest with Hot Tub

Oct 18 – 25

R2,270 ZAR per night
Guest favorite

Farm stay in Middlebury

5.0 out of 5 average rating, 54 reviews

Farm Stay in Amish Country - 2 Bedroom 1 Bath

Sep 10 – 17

R3,087 ZAR per night
Guest favorite

Loft in Shipshewana

4.98 out of 5 average rating, 93 reviews

Hidden Country Hide-A-Way

Feb 10 – 17

R1,680 ZAR per night

Quick stats about vacation 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

R757 ZAR before taxes and fees

Destinations to explore

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