Middlebury, IN Vacation Homes from ₩417,122

A log cabin with red shutters and a small porch.

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Our top choices for Middlebury vacation homes

1. Farm Country Amish Country Newly Renovated

Middlebury

₩417,122 total

includes taxes & fees

Sep 14 - Sep 15

2. Hidden Log Cabin Hot Tub Ping Pong Family

Middlebury

₩453,970 total

includes taxes & fees

Sep 16 - Sep 17

3. Lake House Shallow Sandy Kayaks Family Fun

Shipshewana

₩478,845 total

includes taxes & fees

Sep 13 - Sep 14

4. Lake Front Cottage Kayaks Game Table Fun

Shipshewana

"Loved the cottage! Everything was as stated in the property description and the cottage is decorated very nicely and very clean. Unfortunately, there was severe weather and we had to delay our trip a day. When I asked if we'd be able to get a refund for one day, I got no response from the property manager. However, we accidentally took a book from the cottage and when we texted Todd, he responded immediately and was very helpful in how to return the book. The weather did not cooperate for...

Ron

₩450,163 total

includes taxes & fees

Sep 14 - Sep 15

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Top Middlebury Hotel Reviews

Essenhaus Inn & Conference Center

10/10 Excellent

"Place was very clean. Large property to enjoy and building was far enough away from the main highway that road noise was not an issue. Rooms were much larger than normal hotel rooms. Comfortable bed. The heating and A/C worked better than any other place I have stayed in. Breakfast was decent with coffee and hot chocolate available all day. Nice place to stay!"