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 Jul 19 to Jul 20
$133 total
Jul 19 - Jul 20
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! (1,020 reviews)
"Very"

Reviewed on Jul 14, 2026

Essenhaus Inn & Conference Center
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
$136 nightly
The price is $152 total per night from Aug 2 to Aug 3
$152 total
Aug 2 - Aug 3
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 ...
8.2/10 Very Good! (1,008 reviews)
"Standard hotel located outside of Middlebury with decent sized rooms. Staff was professional but not overly friendly; rooms and common area were tidy but not spotless. For a quick overnight stay, it was fine."

Reviewed on Jul 7, 2026

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 Jul 19 to Jul 20
$188 total
Jul 19 - Jul 20
Total with taxes and fees
Stay at this cottage in Middlebury. Enjoy free WiFi, a garden, and patios. Popular attractions Shipshewana Flea Market and East Lake are located nearby.
10/10 Exceptional! (58 reviews)
"Exceptionally clean and very easy check in/out process."

Reviewed on Jul 2, 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 591 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 patios. Popular attractions Shipshewana Flea Market and East Lake are located nearby.
10/10 Exceptional! (58 reviews)
"Exceptionally clean and very easy check in/out process."

Reviewed on Jul 2, 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
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! (70 reviews)
"This was one of the best properties we have ever stayed at; the pictures don't do justice to the size of a couple of the rooms (bigger than expected, especially with main bathroom) and just loved everything about our stay. Fridge was spotless upon arrival and kitchen had everything we needed; cleaning ..."

Reviewed on Jun 29, 2026

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
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! (28 reviews)
"Perfect location to enjoy Stone Lake. Be prepared for lots of steps but this is not unusual for this side of the lake. Any senior that has knee problems beware. It has a spiral staircase which is dangerous for seniors and young children. The bedrooms are in the basement but do not have an accessible ..."

Reviewed on Jul 6, 2026

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