Middlebury Holiday Homes from £113: Search Holiday Homes in Middlebury

A log cabin with red shutters and a small porch.

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Our top choices for Middlebury holiday homes

A hot tub on a wooden deck with a chair and a blanket.

1. HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Middlebury

Patrick B.

includes taxes & fees

30 Sept - 1 Oct

A hot tub with a view of a grassy field and a cloudy sky.

2. | Hot Tub | Amish Farm Country | Pergola | Deck |

Middlebury

Tim B.

includes taxes & fees

30 Sept - 1 Oct

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

includes taxes & fees

28 Sept - 29 Sept

A house with a white picket fence, a front porch with two rocking chairs, and a brick pathway leading to the door.

4. Charming 3-bedroom house located on Main Street in Downtown Middlebury

Middlebury

Mary W.

A spacious living room with a high ceiling, exposed wooden beams, a brick wall, a staircase, and a large television.

5. The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Middlebury

Dianna D.

includes taxes & fees

25 Oct - 26 Oct

6. | Amish Country Getaway | Farm Views | Fire Pit |

Middlebury

Tamara B.

includes taxes & fees

28 Sept - 29 Sept

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

7. Farm Country Amish Country Newly Renovated

Middlebury

includes taxes & fees

30 Sept - 1 Oct

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

8. Hidden Log Cabin Hot Tub Ping Pong Family

Middlebury

includes taxes & fees

30 Sept - 1 Oct

A small, single-story house with a dark roof, a front porch with two chairs, and a pathway leading to the entrance.

9. Natural Nook | Tiny Home #2 in Amish Country!

Shipshewana

Jeremiah C.

includes taxes & fees

28 Sept - 29 Sept

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

10. 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

includes taxes & fees

28 Sept - 29 Sept

A house with a porch, a window with a flower box, and a chair outside.

11. Millie's Cottage

Shipshewana

BigJohnsCards24

includes taxes & fees

30 Sept - 1 Oct

A two-story house with a front porch, a grill, and a door with a wreath.

12. Beautiful Private Setting !!!

Bristol

Audrey H.

A covered porch with two chairs and a table, a brick wall, and string lights.

13. Superb 5-bedroom farmhouse in Goshen with WiFi, AC

Goshen

Sally F.

includes taxes & fees

29 Sept - 30 Sept

A cozy living room with a sectional sofa, a coffee table, and a floor lamp. There are large windows with curtains, a decorative wall piece, and a view of the outdoors.

14. The Gemini

Elkhart

Kelly C.

includes taxes & fees

4 Oct - 5 Oct

A modern building with a sloped roof, a wooden porch, and a small outdoor seating area.

15. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Shipshewana

Joe R.

includes taxes & fees

28 Sept - 29 Sept

A two-story building with a wooden facade and a metal roof, featuring a porch with chairs and a small garden area.

16. Serene Sanctuary | Tiny Home #1 in Amish Country!

Shipshewana

Karen M.

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with a marble countertop, a built-in oven, and a ceiling fan.

17. Whispering Cottage #3 | Shewana Tiny Home Village

Shipshewana

"The Whispering Cottage exceeded our expectations. It was clean and just the right amount of space for a weekend getaway. The cottage was clean and nicely decorated. The kitchen was fully stocked with dishes, pans, utensils and appliances. Located close to downtown Shipshewana but in a serene, quiet area with sheep, horses and goats right out our back door. Landon was very responsive to questions. Highly recommend and we will definitely stay again."

Jeff D.

includes taxes & fees

28 Sept - 29 Sept

A cozy room with wicker chairs, a rocking chair, a teal rug, and a sign reading "Welcome to our Lake House."

18. Lake Front Cottage | Kayaks | Game Table Fun

Shipshewana

Andrea S.

includes taxes & fees

28 Sept - 29 Sept

A view from a balcony overlooking a frozen lake with bare trees and a clear sky.

19. Live & Love Life on the Lake at Sunset Peak!

Howe

Ron O.

includes taxes & fees

29 Sept - 30 Sept

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

20. Lake House Shallow Sandy Kayaks Family Fun

Shipshewana

includes taxes & fees

1 Oct - 2 Oct

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Top Middlebury Hotel Reviews

Super 8 by Wyndham Shipshewana

8/10 Good

"It’s good breakfast and clean"

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

10/10 Excellent

"Mike and Amy are very good hosts. Their place is very comfortable and the setting in the country is picturesque. They have the most comfortable lazy boy type chairs we have every run across. We would only mention the check-in process. The keypad lock on the door only works at 4:00PM or later. If you get there a little ahead of time you have to wait. Otherwise, we would highly recommend it."

Find out more about Middlebury

Middlebury Holiday Homes information

Number of reviews	714
Accommodation	242 Holiday Homes
Lowest Price	£113
Highest Price	£365

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlebury holiday homes

1. HOT TUB | Beautiful Backyard Oasis|Newly Renovated

2. | Hot Tub | Amish Farm Country | Pergola | Deck |

3. Amish Country Getaway Farm Views Fire Pit

4. Charming 3-bedroom house located on Main Street in Downtown Middlebury

5. The Back Porch Haven Stay in Amish Country yet close to Notre Dame

6. | Amish Country Getaway | Farm Views | Fire Pit |

7. Farm Country Amish Country Newly Renovated

8. Hidden Log Cabin Hot Tub Ping Pong Family

9. Natural Nook | Tiny Home #2 in Amish Country!

10. Lake Front Cottage Kayaks Game Table Fun

11. Millie's Cottage

12. Beautiful Private Setting !!!

13. Superb 5-bedroom farmhouse in Goshen with WiFi, AC

14. The Gemini

15. Hearthstone Hideaway #5 | Shewana Tiny Home Village

16. Serene Sanctuary | Tiny Home #1 in Amish Country!

17. Whispering Cottage #3 | Shewana Tiny Home Village

18. Lake Front Cottage | Kayaks | Game Table Fun

19. Live & Love Life on the Lake at Sunset Peak!

20. Lake House Shallow Sandy Kayaks Family Fun

Find holiday rentals that suit your style

Top Middlebury Hotel Reviews

Super 8 by Wyndham Shipshewana

Travelodge by Wyndham Elkhart

Der Ruhe Blatz Motel

Hampton Inn & Suites Middlebury

La Quinta Inn & Suites by Wyndham Elkhart

Blue Gate Garden Inn

The Garden Inn

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Sleep Inn Elkhart North

Find out more about Middlebury

Middlebury Holiday Homes information

Explore a world of travel with Expedia