3/5 - Okay
Verified traveler
The roads are too straight and flat
Visit Middlebury
Hampton Inn & Suites Middlebury
105 Crystal Heights Blvd Middlebury IN
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $120 total per night from Jan 4 to Jan 5
$120 total
Jan 4 - Jan 5, 2026
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! (1,006 reviews)
Clean room it cold when we arrived on a winter day. Musty smell initially but better as room warmed up. Large room accommodated daughter in wheelchair perfectly.
Reviewed on Nov 28, 2025
Essenhaus Inn & Conference Center
240 Hwy 20 Middlebury IN
$109 nightly
The price is $122 total per night from Dec 7 to Dec 8
$122 total
Dec 7 - Dec 8
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! (1,000 reviews)
Great staff Great room Clean pool/spa Great food Great service
Reviewed on Dec 2, 2025
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury IN
$135 nightly
The price is $144 total per night from Dec 14 to Dec 15
$144 total
Dec 14 - Dec 15
Total with taxes and 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! (41 reviews)
Upon arrival the host checked in with us to verify ID and see if there was anything we needed. Rental was as described, and met our needs during our trip.
Reviewed on Nov 23, 2025
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
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! (41 reviews)
Upon arrival the host checked in with us to verify ID and see if there was anything we needed. Rental was as described, and met our needs during our trip.
Reviewed on Nov 23, 2025
The Wellington Cottage
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
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
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
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.
Deutsch Kase Haus
Enjoy an outing to Deutsch Kase Haus during your stay in Middlebury. While in this relaxing area, find time to visit its shops.
Meadow Valley Golf Club
Enjoy a round of golf in Middlebury at Meadow Valley Golf Club. While in this family-friendly area, you can enjoy the restaurants.
Corson Riverwoods County Park
After visiting Corson Riverwoods County Park, make a plan to see the other sights and activities in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Middlebury Community Historical
You can spend an afternoon studying the exhibits at Middlebury Community Historical in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
East Park
After visiting East Park, make a plan to see the other sights and activities in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Reviews of Middlebury
4.5
Top Destination
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.
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