Middlebury Holiday Homes from ฿8,115: 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

A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

1. Amish Country Getaway Farm Views Fire Pit

Middlebury

฿8,910 total

includes taxes & fees

5 Oct - 6 Oct

A kitchen with a double sink, light-colored cabinets, and a refrigerator.

2. Farm Country Amish Country Newly Renovated

Middlebury

฿9,694 total

includes taxes & fees

6 Oct - 7 Oct

A log cabin interior with a dining area, a living room, a staircase, and a coffee bar.

3. Hidden Log Cabin Hot Tub Ping Pong Family

Middlebury

฿21,997 total

includes taxes & fees

16 Oct - 17 Oct

A cozy seating area with wicker chairs and a teal rug, a 'Welcome to our Lake House' sign, and nautical decorations.

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

฿8,115 total

includes taxes & fees

5 Oct - 6 Oct

A spacious living room with a wooden dining table, chairs, a television, and a large window with curtains.

5. Lake House Shallow Sandy Kayaks Family Fun

Shipshewana

฿13,204 total

includes taxes & fees

6 Oct - 7 Oct

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Top Middlebury Hotel Reviews

Blue Gate Garden Inn

10/10 Excellent

"Great staff! I only stayed at the hotel for a few hours because something came up and I had to check out unfortunately. Staff was super friendly and I was really disappointed I mussed the breakfast"