A log cabin with red shutters and a small porch.

Search Vacation 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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Middlebury vacation 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)
"This is a great Property!"
United States
Patrick B.
The price is ￥17,831
￥41,523 total
includes taxes & fees
Sep 30 - Oct 1
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

2. Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit
2.0 star property
Middlebury
The price is ￥18,729
￥42,088 total
includes taxes & fees
Sep 28 - Sep 29
Amish Country Getaway Farm Views Fire Pit
A hot tub with a view of a grassy field and a cloudy sky.

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

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (103 reviews)
"This was a warm and cozy stay! "
United States
Tim B.
The price is ￥16,716
￥41,995 total
includes taxes & fees
Sep 30 - Oct 1
| Hot Tub | Amish Farm Country | Pergola | Deck |
A spacious living room with a high ceiling, exposed wooden beams, a brick wall, a staircase, and a large television.

4. 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 ￥20,955
￥48,751 total
includes taxes & fees
Oct 25 - Oct 26
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
A log cabin interior with a dining area, a living room with a sofa and armchair, a coffee bar, and a wooden staircase.

5. Hidden Log Cabin | Hot Tub | Ping Pong | Family |

Hidden Log Cabin | Hot Tub | Ping Pong | Family |
Goshen
10.0 out of 10, Exceptional, (16 reviews)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
The price is ￥27,118
￥55,683 total
includes taxes & fees
Sep 30 - Oct 1
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.

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

| Amish Country Getaway | Farm Views | Fire Pit |
Middlebury
10.0 out of 10, Exceptional, (3 reviews)
"Great location! Close to Shipshewana and shopping and restaurants. Extremely clean, roomy, and had everything you need for a great stay."
United States
Tamara B.
The price is ￥15,973
￥38,192 total
includes taxes & fees
Sep 28 - Sep 29
| Amish Country Getaway | Farm Views | Fire Pit |
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

7. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is ￥20,688
￥47,191 total
includes taxes & fees
Sep 30 - Oct 1
Farm Country Amish Country Newly Renovated
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

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is ￥83,588
￥116,416 total
includes taxes & fees
Oct 16 - Oct 17
Hidden Log Cabin Hot Tub Ping Pong Family
A two-story building with a wooden facade and a metal roof, featuring a porch with chairs and a small garden area.

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

Serene Sanctuary | Tiny Home #1 in Amish Country!
Shipshewana
10.0 out of 10, Exceptional, (6 reviews)
"Loved the tiny house "
United States
Karen M.
The price is ￥14,624
￥38,841 total
includes taxes & fees
Sep 27 - Sep 28
Serene Sanctuary | Tiny Home #1 in Amish Country!
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

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 ￥20,059
￥42,456 total
includes taxes & fees
Sep 28 - Sep 29
Lake Front Cottage Kayaks Game Table Fun
A house with a porch, a window with a flower box, and a chair outside.

11. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (324 reviews)
"Great property. Good location. Would stay again."
United States
BigJohnsCards24
The price is ￥22,791
￥33,126 total
includes taxes & fees
Oct 4 - Oct 5
Millie's Cottage
A two-story house with a front porch, a grill, and a door with a wreath.

12. Beautiful Private Setting !!!

Beautiful Private Setting !!!
Bristol
10.0 out of 10, Exceptional, (29 reviews)
"Great setting and well supplied. "
United States
Audrey H.
Beautiful Private Setting !!!
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

Superb 5-bedroom farmhouse in Goshen with WiFi, AC
Goshen
9.8 out of 10, Exceptional, (50 reviews)
"We had a great stay!!"
United States
Sally F.
The price is ￥39,409
￥47,926 total
includes taxes & fees
Sep 27 - Sep 28
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
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

The Gemini
Elkhart
9.2 out of 10, Wonderful, (15 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 ￥18,375
￥23,049 total
includes taxes & fees
Oct 6 - Oct 7
The Gemini
A modern building with a sloped roof, a wooden porch, and a small outdoor seating area.

15. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Hearthstone Hideaway #5 | Shewana Tiny Home Village
Shipshewana
9.6 out of 10, Exceptional, (7 reviews)
"We enjoyed staying at the tiny house. Was clean and quiet. Had about everything we needed for are two night stay. Will be back"
United States
Joe R.
The price is ￥14,669
￥33,482 total
includes taxes & fees
Sep 28 - Sep 29
Hearthstone Hideaway #5 | Shewana Tiny Home Village
A small, single-story house with a dark roof, a front porch with two chairs, and a pathway leading to the entrance.

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

Natural Nook | Tiny Home #2 in Amish Country!
Shipshewana
9.8 out of 10, Exceptional, (21 reviews)
"If you're looking for a peaceful, beautiful place, this tiny house is it! Tranquil and everything you need for a weekend getaway."
United States
Michelle H.
The price is ￥14,624
￥38,841 total
includes taxes & fees
Sep 27 - Sep 28
Natural Nook | Tiny Home #2 in Amish Country!
A small wooden cabin with a pitched roof, a front door, and two chairs outside.

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

Nature's Nest | Tiny Home #4 in Amish Country!
Shipshewana
10.0 out of 10, Exceptional, (14 reviews)
"Very clean, quiet and cosy. For being a tiny house we had anything we needed. Location is great.The bed and mattress were very comfortable"
United States
L D.
The price is ￥14,669
￥33,482 total
includes taxes & fees
Sep 28 - Sep 29
Nature's Nest | Tiny Home #4 in Amish Country!
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

Lake Front Cottage | Kayaks | Game Table Fun
Shipshewana
9.2 out of 10, Wonderful, (10 reviews)
"Lake Front Cottage was perfect for our weekend stay in LaGrange County. The host was responsive in communication and provided everything we needed for a pleasant stay."
United States
Andrea S.
The price is ￥18,388
￥37,605 total
includes taxes & fees
Sep 28 - Sep 29
Lake Front Cottage | Kayaks | Game Table Fun
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!

Live & Love Life on the Lake at Sunset Peak!
Howe
9.8 out of 10, Exceptional, (48 reviews)
"Lovely place to stay and so close to water. "
United States
Ron O.
The price is ￥22,860
￥50,022 total
includes taxes & fees
Sep 27 - Sep 28
Live & Love Life on the Lake at Sunset Peak!
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

Lake House Shallow Sandy Kayaks Family Fun
2.0 star property
Shipshewana
The price is ￥41,740
￥80,315 total
includes taxes & fees
Oct 1 - Oct 2
Lake House Shallow Sandy Kayaks Family Fun
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

The Garden Inn

The Garden Inn

8/10 Good
"My room was fine. This hotel is in a sad state of repair. The check-in procedure is via zoom type meeting which doesn't work well if you're hearing-impaired."
john 1-night trip
Posted 2 hours ago
The Garden Inn

Find out more about Middlebury

Middlebury Vacation Homes information

Number of reviews
710
Accommodation
245 Vacation Homes
Lowest Price
￥23,049
Highest Price
￥116,416