Middlebury, IN

Travel Guide

Photo by Ann Sair
Photo by Jw
Photo by Patrick Laughlin 
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
The price is ¥17,393 per night from Dec 1 to Dec 2
¥17,393
¥19,480 total
Dec 1 - Dec 2
includes taxes & 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! (1,001 reviews)
Great experience

Reviewed on Nov 16, 2025

Hampton Inn & Suites Middlebury
Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

3.5 out of 5
240 Hwy 20 Middlebury IN
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! (1,006 reviews)
Rooms were great. Staff wonderful and Inn very lovely.

Reviewed on Nov 13, 2025

Essenhaus Inn & Conference Center
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

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

2 out of 5
Middlebury IN
The price is ¥17,987 per night from Nov 30 to Dec 1
¥17,987
¥22,593 total
Nov 30 - Dec 1
includes taxes & fees
Stay at this cottage in Middlebury. Enjoy free WiFi, a garden, and patios. Popular attractions East Lake and Hunter Lake are located nearby.
9.8/10 Exceptional! (40 reviews)
Very nice and clean space. It's in a very quiet area but only a few minutes off the interstate and not hard to find.

Reviewed on Oct 28, 2025

Charming 2-bedroom cottage with WiFi, AC in peaceful 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

2 out of 5
Middlebury IN
Stay at this cottage in Middlebury. Enjoy free WiFi, a garden, and patios. Popular attractions East Lake and Hunter Lake are located nearby.
9.8/10 Exceptional! (40 reviews)
Very nice and clean space. It's in a very quiet area but only a few minutes off the interstate and not hard to find.

Reviewed on Oct 28, 2025

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! (62 reviews)
The host was very welcoming and made sure everything was to our satisfaction. The house was clean and nice and in a quiet neighborhood. We had a very enjoyable stay.

Reviewed on Nov 1, 2025

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
The Wellington Cottage

The Wellington Cottage

3 out of 5
7420 N 1160 W Middlebury IN
Book a stay at this family-friendly cottage in Middlebury. Enjoy free WiFi, free parking, and a 24-hour business center. Popular attractions Stone Lake and Brokesha ...
10/10 Exceptional! (5 reviews)
The cottage is adorable and well stocked for travelers!! I wish I could have stayed and enjoyed the beautiful fall lake views! The area and surrounding houses are well kept and seem quite safe! Easy access and convenient parking. I regret forgetting to read the previous ones or leave a note with ...

Reviewed on Nov 6, 2025

The Wellington Cottage
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.

Popular places to visit

Reviews of Middlebury

4.5
Top Destination
5 - Excellent
43
5 - Excellent 59%
4 - Good
22
4 - Good 30%
3 - Okay
8
3 - Okay 11%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

3/5 - Okay

Verified traveler

The roads are too straight and flat

5/5 - Excellent

Verified traveler

Friendly people. If we'd have had time, we'd have gone to Rise N Roll, an Amish bakery right along US 20, east of Middlebury several miles.

5/5 - Excellent

Verified traveler

Middlebury is a quaint small town with interesting shops that I would love to go back to.

5/5 - Excellent

Verified traveler

Been here before. Little, quiet and out of the way.

4/5 - Good

Verified traveler

The bakery near the Essenhaus Inn & Conference Center has the best baked goods, and the restaurant near the Center serves delicious food.

4/5 - Good

Verified traveler

We would highly recommend seeing a play while there. The actors are mostly all local and do a great job.

Cities near Middlebury