A log cabin with red shutters and a small porch.

Holiday Homes in Middlebury

  • 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Middlebury
10.0 out of 10, Exceptional, (77 reviews)
"Great location"
United States
Tracy C.
The price is NZ$636
includes taxes & fees
1 Nov - 2 Nov
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
A hot tub with a view of a grassy field and a cloudy sky.

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

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (104 reviews)
"This was a warm and cozy stay! "
United States
Tim B.
| Hot Tub | Amish Farm Country | Pergola | Deck |
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 |

| Amish Country Getaway | Farm Views | Fire Pit |
Middlebury
10.0 out of 10, Exceptional, (6 reviews)
"Great little farmhouse for the family."
United States
Arlen K.
| Amish Country Getaway | Farm Views | Fire Pit |
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

4. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is NZ$516
includes taxes & fees
27 Oct - 28 Oct
Farm Country Amish Country Newly Renovated
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

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Middlebury
10.0 out of 10, Exceptional, (34 reviews)
"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."
United States
Dianna D.
The price is NZ$597
includes taxes & fees
26 Oct - 27 Oct
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
A log cabin interior with a dining area, a living room, a staircase, and a coffee bar.

6. Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
Hidden Log Cabin Hot Tub Ping Pong Family
A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

7. Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit
2.0 star property
Middlebury
Amish Country Getaway Farm Views Fire Pit
A small, single-story house with a dark roof, a front porch with two chairs, and a pathway leading to the entrance.

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

Natural Nook | Tiny Home #2 in Amish Country!
Shipshewana
9.8 out of 10, Exceptional, (22 reviews)
"It was quite and peaceful… beautiful setting… loved the tiny house"
United States
Carla
The price is NZ$422
includes taxes & fees
22 Oct - 23 Oct
Natural Nook | Tiny Home #2 in Amish Country!
A house with a porch, a window with a flower box, and a chair outside.

9. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (332 reviews)
"Great place to stay"
United States
Joshua H.
The price is NZ$344
includes taxes & fees
3 Nov - 4 Nov
Millie's Cottage
A lakeside seating area with Adirondack chairs and a canoe, surrounded by a grassy area and a large tree.

10. Lake House | Shallow Sandy | Kayaks | Family Fun

Lake House | Shallow Sandy | Kayaks | Family Fun
Middlebury
9.8 out of 10, Exceptional, (14 reviews)
"Great house for a friends getaway. The house is fully equipped to enjoy meals, relax and enjoy the lake. Loved the coffee set up and small extras for guest to enjoy."
United States
Angela D.
Lake House | Shallow Sandy | Kayaks | Family Fun
A cozy seating area with wicker chairs and a teal rug, a 'Welcome to our Lake House' sign, and nautical decorations.

11. Lake Front Cottage Kayaks Game Table Fun

Lake Front Cottage Kayaks Game Table Fun
2.0 star property
Shipshewana
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Ron
Lake Front Cottage Kayaks Game Table Fun
A covered porch with two chairs and a table, a brick wall, and string lights.

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

Superb 5-bedroom farmhouse in Goshen with WiFi, AC
Goshen
9.8 out of 10, Exceptional, (54 reviews)
"We had a great stay!!"
United States
Sally F.
The price is NZ$682
includes taxes & fees
31 Oct - 1 Nov
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
A kitchenette with a coffee maker, a mug, a bowl, and a shelf with coffee containers.

13. Songbird Haven, 3 min from town, Pumpkinvine, MEC,concerts. 3 bedroom, 2 bath.

Songbird Haven, 3 min from town, Pumpkinvine, MEC,concerts. 3 bedroom, 2 bath.
Shipshewana
9.6 out of 10, Exceptional, (47 reviews)
"I would highly recommend this place to anyone, we will book it for our next trip back to Shipshewana. It is a very quiet location, the beds are super comfy and there is plenty of space."
Canada
Maria
Songbird Haven, 3 min from town, Pumpkinvine, MEC,concerts. 3 bedroom, 2 bath.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a wooden dining table with bar stools.

14. Kayaks | Relax by River | 10 Min to Shipshewana |

Kayaks | Relax by River | 10 Min to Shipshewana |
Howe
10.0 out of 10, Exceptional, (31 reviews)
"We had a great stay. It was really clean and comfortable, and I loved being able to kayak. It was a perfect place for a relaxing few days."
United States
Christine C.
The price is NZ$406
includes taxes & fees
26 Oct - 27 Oct
Kayaks | Relax by River | 10 Min to Shipshewana |
Exterior

15. Hilltop Family Retreat

Hilltop Family Retreat
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Well maintained and had everything you could need!"
United States
Rosie B.
The price is NZ$1,163
includes taxes & fees
2 Nov - 3 Nov
Hilltop Family Retreat
A modern building with a sloped roof, a wooden porch, and a small outdoor seating area.

16. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Hearthstone Hideaway #5 | Shewana Tiny Home Village
Shipshewana
9.6 out of 10, Exceptional, (10 reviews)
"I cannot even explain how clean the property was. The place we stayed was amazingly clean and any problems we had all we had to do was reach out with the host and they got back to us within 15 to 20 minutes. This was one of the most amazing stays I’ve been at thank you for an amazing getaway."
United States
Wendy
Hearthstone Hideaway #5 | Shewana Tiny Home Village
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.

17. The Gemini

The Gemini
Elkhart
9.2 out of 10, Wonderful, (16 reviews)
"Very clean, had everything we needed and the host was great to communicate with. One of the best places we have ever stayed."
United States
Kelly C.
The price is NZ$257
includes taxes & fees
31 Oct - 1 Nov
The Gemini
A two-story building with a wooden facade and a metal roof, featuring a porch with chairs and a small garden area.

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

Serene Sanctuary | Tiny Home #1 in Amish Country!
Shipshewana
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful time!"
United States
Julie G.
Serene Sanctuary | Tiny Home #1 in Amish Country!
A long table with candles and greenery, set against a wooden backdrop with vertical strings of lights.

19. Rock Run Creek House

Rock Run Creek House
Goshen
9.6 out of 10, Exceptional, (5 reviews)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
The price is NZ$1,163
includes taxes & fees
2 Nov - 3 Nov
Rock Run Creek House
A modern kitchen with a marble countertop, a built-in oven, and a ceiling fan.

20. Whispering Cottage #3 | Shewana Tiny Home Village

Whispering Cottage #3 | Shewana Tiny Home Village
Shipshewana
9.4 out of 10, Exceptional, (13 reviews)
"Very awesome place. A bit overpriced but still a good deal and experience."
United States
Edward D.
Whispering Cottage #3 | Shewana Tiny Home Village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlebury Hotel Reviews

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

10/10 Excellent
"Just stayed the night, but everything was clean and made you feel welcome"
Jerry 1-night trip
Posted 5 hours ago
Essenhaus Inn & Conference Center

Find out more about Middlebury

Middlebury Holiday Homes information

Number of reviews
751
Accommodation
241 Holiday Homes
Lowest Price
NZ$257
Highest Price
NZ$1,163