Middlebury Private Holiday Homes

A log cabin with red shutters and a small porch.

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Our top choices for Middlebury holiday homes

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

1. Farm Country Amish Country Newly Renovated

Middlebury

RM1,178 total

includes taxes & fees

6 Oct - 7 Oct

A modern bathroom with a granite sink, a mirror, a towel rack, and a basket of towels.

2. Amish Country Getaway Farm Views Fire Pit

Middlebury

RM1,083 total

includes taxes & fees

12 Oct - 13 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

RM2,159 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

RM990 total

includes taxes & fees

12 Oct - 13 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

RM1,527 total

includes taxes & fees

6 Oct - 7 Oct

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Top Middlebury Hotel Reviews

Farmstead Inn & Conference Center

8/10 Good

"Clean room. Friendly, helpful staff. Breakfast was good. Room was standard."

Best Western Plus Howe Inn

10/10 Excellent

"Dawn was delightful at check-in. She pointed out filtered water /ice station, which was handy. We got to enjoy the pool area and had it all to ourselves. The room was spacious, and I really love the way hotels are doing soaps and lotions in bottles on the wall. The breakfast was great - check out the latte machine and waffle makers towards the back. A perfect systems. A great place to break up a long trip through Ohio and Indiana."

Super 8 by Wyndham Shipshewana

8/10 Good

"It is a no-frills hotel, but the room was clean and the bed was comfortable. It was also within walking distance to the performing arts center so that we could walk to and from the concert that we were in town for. I have a dairy allergy so breakfast was really not available for me other than a basic bagel. Although it is not necessarily walking distance to downtown, it is very convenient to drive to and from."

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