Photo by Ann Sair

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Our top choices for Middlebury vacation homes

1. | 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.
The price is ¥19,799
¥42,412 total
includes taxes & fees
Nov 23 - Nov 24
| Hot Tub | Amish Farm Country | Pergola | Deck |

2. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is ¥24,071
¥48,581 total
includes taxes & fees
Nov 23 - Nov 24
Farm Country Amish Country Newly Renovated

3. 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, (36 reviews)
"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."
United States
Dianna D.
The price is ¥24,602
¥54,176 total
includes taxes & fees
Nov 17 - Nov 18
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

4. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Hearthstone Hideaway #5 | Shewana Tiny Home Village
Shipshewana
9.6 out of 10, Exceptional, (13 reviews)
"Very nice stay! Our only negative was that there were more vehicles than parking spaces."
United States
Rita S.
The price is ¥16,621
¥34,447 total
includes taxes & fees
Nov 16 - Nov 17
Hearthstone Hideaway #5 | Shewana Tiny Home Village

5. 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
The price is ¥15,835
¥34,564 total
includes taxes & fees
Nov 24 - Nov 25
Lake Front Cottage Kayaks Game Table Fun

6. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (338 reviews)
"Great place to stay"
United States
Joshua H.
The price is ¥21,427
¥29,752 total
includes taxes & fees
Nov 16 - Nov 17
Millie's Cottage

7. 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, (56 reviews)
"We had a great stay!!"
United States
Sally F.
The price is ¥39,521
¥57,063 total
includes taxes & fees
Nov 16 - Nov 17
Superb 5-bedroom farmhouse in Goshen with WiFi, AC

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

Natural Nook | Tiny Home #2 in Amish Country!
Shipshewana
9.8 out of 10, Exceptional, (23 reviews)
"It was quite and peaceful… beautiful setting… loved the tiny house"
United States
Carla
The price is ¥16,621
¥39,375 total
includes taxes & fees
Nov 16 - Nov 17
Natural Nook | Tiny Home #2 in Amish Country!

9. Whispering Cottage #3 | Shewana Tiny Home Village

Whispering Cottage #3 | Shewana Tiny Home Village
Shipshewana
9.4 out of 10, Exceptional, (15 reviews)
"Beautiful and peaceful place."
United States
Jackie S.
The price is ¥16,621
¥34,447 total
includes taxes & fees
Nov 16 - Nov 17
Whispering Cottage #3 | Shewana Tiny Home Village

10. 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.
The price is ¥16,621
¥39,375 total
includes taxes & fees
Nov 18 - Nov 19
Serene Sanctuary | Tiny Home #1 in Amish Country!

11. Riverhaven! Glamorous A-Frame on St Joe River!

Riverhaven! Glamorous A-Frame on St Joe River!
Bristol
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful place to stay! The home was very clean and the location was perfect!"
United States
Emmajo R.
The price is ¥36,883
¥74,339 total
includes taxes & fees
Nov 16 - Nov 17
Riverhaven! Glamorous A-Frame on St Joe River!

12. Little Luxe Retreat #7 | Tiny Home + Fire Table

Little Luxe Retreat #7 | Tiny Home + Fire Table
Shipshewana
10.0 out of 10, Exceptional, (18 reviews)
"Very cozy and well kept up!"
United States
Randy R.
The price is ¥16,621
¥39,558 total
includes taxes & fees
Nov 24 - Nov 25
Little Luxe Retreat #7 | Tiny Home + Fire Table

13. The Gemini

The Gemini
Elkhart
9.4 out of 10, Exceptional, (18 reviews)
"Nice place"
United States
Karla
The price is ¥18,427
¥20,567 total
includes taxes & fees
Nov 17 - Nov 18
The Gemini

14. Simple Serenity Loft | Tiny Home #6 in Amish Country!

Simple Serenity Loft | Tiny Home #6 in Amish Country!
Shipshewana
9.6 out of 10, Exceptional, (10 reviews)
"The place was beautiful and very clean and close to town.It was very peaceful and quiet."
United States
audrey o.
The price is ¥16,621
¥39,375 total
includes taxes & fees
Nov 17 - Nov 18
Simple Serenity Loft | Tiny Home #6 in Amish Country!

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 ¥73,011
¥102,452 total
includes taxes & fees
Nov 17 - Nov 18
Hilltop Family Retreat

16. Nature's Nest | Tiny Home #4 in Amish Country!

Nature's Nest | Tiny Home #4 in Amish Country!
Shipshewana
9.8 out of 10, Exceptional, (15 reviews)
"Great place to stay"
United States
Bill L.
The price is ¥16,621
¥34,447 total
includes taxes & fees
Nov 17 - Nov 18
Nature's Nest | Tiny Home #4 in Amish Country!

17. Rock Run Creek House

Rock Run Creek House
Goshen
9.6 out of 10, Exceptional, (5 reviews)
"Close to Shipshe and a beautiful property"
United States
Holly A.
The price is ¥73,011
¥102,452 total
includes taxes & fees
Nov 17 - Nov 18
Rock Run Creek House

18. Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa

Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa
Elkhart
6.8 out of 10, (3 reviews)
"We came here with 8 people, four young kids, we had fun in the hot tub and the sleeping arraignments were great, beds were comfortable enough and the kids loved the swim spa, and the view is super cool, watching birds and wild life in the river. We would recommend this place even in the winter. "
United States
Cara H.
The price is ¥36,998
¥75,762 total
includes taxes & fees
Nov 16 - Nov 17
Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa

19. Klinger Lake Cove - Sleeps 16-24

Klinger Lake Cove - Sleeps 16-24
White Pigeon
10.0 out of 10, Exceptional, (6 reviews)
"It was a nice place. we wanted a weekend getaway with family and it was perfect."
United States
Haxhi
The price is ¥69,996
¥123,240 total
includes taxes & fees
Nov 18 - Nov 19
Klinger Lake Cove - Sleeps 16-24

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

Live & Love Life on the Lake at Sunset Peak!
Howe
9.8 out of 10, Exceptional, (51 reviews)
"Wonderful location! Great swimming, kayaks, view! Place was clean and perfect for our stay"
United States
Ellie B.
The price is ¥21,425
¥46,504 total
includes taxes & fees
Nov 16 - Nov 17
Live & Love Life on the Lake at Sunset Peak!
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.

Learn more about Middlebury

Amish heritage comes alive at the Das Dutchman Essenhaus, where you can savor homemade pies after shopping for handcrafted quilts. Rent bikes to explore the scenic Pumpkinvine Nature Trail, stopping at family-owned shops for authentic Amish cheese and freshly baked bread.

A Dutch County building with a covered walkway and red wagon wheels.
Photo by Ann Sair
Open Photo by Ann Sair