Middlebury Vacation Home Rentals from P18,228: Search Top Private Vacation Homes for Rent

A log cabin with red shutters and a small porch.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Middlebury vacation homes

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

1. Farm Country Amish Country Newly Renovated

Middlebury

P18,228 total

includes taxes & fees

Oct 27 - Oct 28

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

2. Hidden Log Cabin Hot Tub Ping Pong Family

Middlebury

P28,042 total

includes taxes & fees

Nov 23 - Nov 24

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

3. Amish Country Getaway Farm Views Fire Pit

Middlebury

P19,850 total

includes taxes & fees

Nov 10 - Nov 11

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

4. Lake House Shallow Sandy Kayaks Family Fun

Shipshewana

P21,736 total

includes taxes & fees

Oct 28 - Oct 29

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

5. 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...