Middlebury Holiday Homes from Rp5.458.924: Search Top Rental Houses in Middlebury

A log cabin with red shutters and a small porch.

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Our top choices for Middlebury holiday homes

1. Amish Country Getaway Farm Views Fire Pit

Middlebury

2. Hidden Log Cabin Hot Tub Ping Pong Family

Middlebury

Rp6.410.083 total

includes taxes & fees

10 Sept - 11 Sept

3. Lake House Shallow Sandy Kayaks Family Fun

Shipshewana

Rp6.480.930 total

includes taxes & fees

25 Aug - 26 Aug

4. Secluded Shipshewana Log Cabin In the Woods

Shipshewana

Rp5.458.924 total

includes taxes & fees

20 Sept - 21 Sept

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Top Middlebury Hotel Reviews

Farmstead Inn & Conference Center

10/10 Excellent

"8/2026 Staff was friendly gave us all the information on Breakfast that was very good and the pool nice and large open till 11 the hot tub is not open yet the listing didn't say they had a hot tub they are building a New Pool and hot tub Room was very nice pricing was good for the area arrive early most things close by 4 in the area some things are open until 7 (Love this site)"