Middlebury, IN

Travel Guide

A log cabin with red shutters and a small porch.
A horse-drawn carriage with a covered wagon, parked on a dirt path with grass and trees in the background.
A black carriage with two horses tied to it, parked on a street.
A row of empty boats docked by a calm river, surrounded by trees with autumn foliage.
A Dutch County building with a covered walkway and red wagon wheels.
Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

3.5 out of 5
240 Hwy 20 Middlebury IN
$119 nightly
The price is $133 total per night from Aug 9 to Aug 10
$133 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Middlebury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.6/10 Exceptional! (1,015 reviews)
"Great property. quick access to pumpkin trail. Great breakfast. Beds good be alittle softer"

Reviewed on Aug 8, 2026

Essenhaus Inn & Conference Center
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
$106 nightly
The price is $119 total per night from Sep 3 to Sep 4
$119 total
Sep 3 - Sep 4
Total with taxes and fees
Stay at this hotel in Middlebury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Hampton Inn & Suites Middlebury
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Middlebury IN
$176 nightly
The price is $188 total per night from Aug 9 to Aug 10
$188 total
Aug 9 - Aug 10
Total with taxes and fees
Stay at this cottage in Middlebury. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions East Lake and Hunter Lake are located ...
10/10 Exceptional! (64 reviews)
"Very clean throughout house. It was great to see the horses in the fenced in area behind house."

Reviewed on Aug 5, 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 602 properties in Middlebury
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Middlebury IN
Stay at this cottage in Middlebury. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions East Lake and Hunter Lake are located ...
10/10 Exceptional! (64 reviews)
"Very clean throughout house. It was great to see the horses in the fenced in area behind house."

Reviewed on Aug 5, 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Middlebury IN
Stay at this vacation home in Middlebury. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Brokesha Lake and Stone Lake are ...
9.6/10 Exceptional! (29 reviews)
"Great lake home to stay at for our mother/daughter weekend. It's very close to both Shipshewana and Middlebury."

Reviewed on Jul 23, 2026

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Middlebury IN
Stay at this vacation home in Middlebury. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Memorial Park and East Park are located ...
10/10 Exceptional! (73 reviews)
"Great place to stay."

Reviewed on Aug 4, 2026

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
See all properties in Middlebury
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Middlebury attractions

Stone Lake

Commune with nature and explore the great outdoors at Stone Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
See properties

Cities near Middlebury

An aerial view of a town with a prominent clock tower, a central green space, and a main street lined with trees and parked cars.

Goshen

An industrial area with large warehouses, a parking lot, and a road with vehicles.

Shipshewana

A windmill, a red barn, and snow-covered trees.

Bristol

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