A log cabin with red shutters and a small porch.

Middlebury Vacation Rentals

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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 CA $159
CA $367 total
includes taxes & fees
Sep 30 - Oct 1
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, (103 reviews)
"This was a warm and cozy stay! "
United States
Tim B.
The price is CA $147
CA $369 total
includes taxes & fees
Sep 30 - Oct 1
| 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
2.0 star property
Middlebury
The price is CA $167
CA $375 total
includes taxes & fees
Sep 28 - Sep 29
Amish Country Getaway Farm Views Fire Pit
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

Charming 3-bedroom house located on Main Street in Downtown Middlebury
Middlebury
9.6 out of 10, Exceptional, (26 reviews)
"Nice clean conveniently located to visit all the area has to offer."
United States
Mary W.
Charming 3-bedroom house located on Main Street in Downtown Middlebury
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 CA $187
CA $462 total
includes taxes & fees
Oct 25 - Oct 26
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
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 CA $142
CA $343 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 CA $173
CA $408 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 CA $268
CA $528 total
includes taxes & fees
Sep 30 - Oct 1
Hidden Log Cabin Hot Tub Ping Pong Family
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!

Natural Nook | Tiny Home #2 in Amish Country!
Shipshewana
9.8 out of 10, Exceptional, (21 reviews)
"Everything was very clean and ready for our stay. We had a great time."
United States
Jeremiah C.
The price is CA $131
CA $345 total
includes taxes & fees
Sep 28 - Sep 29
Natural Nook | Tiny Home #2 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 CA $171
CA $370 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 CA $204
CA $293 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $352
CA $431 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $164
CA $206 total
includes taxes & fees
Oct 2 - Oct 3
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 CA $131
CA $300 total
includes taxes & fees
Sep 28 - Sep 29
Hearthstone Hideaway #5 | Shewana Tiny Home Village
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!

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 CA $137
CA $355 total
includes taxes & fees
Oct 4 - Oct 5
Serene Sanctuary | Tiny Home #1 in Amish Country!
A modern kitchen with a marble countertop, a built-in oven, and a ceiling fan.

17. Whispering Cottage #3 | Shewana Tiny Home Village

Whispering Cottage #3 | Shewana Tiny Home Village
Shipshewana
8.8 out of 10, Excellent, (8 reviews)
"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."
United States
Jeff D.
The price is CA $131
CA $300 total
includes taxes & fees
Sep 28 - Sep 29
Whispering Cottage #3 | Shewana Tiny Home Village
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 CA $157
CA $332 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, (49 reviews)
"Lovely place to stay and so close to water. "
United States
Ron O.
The price is CA $197
CA $464 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $336
CA $674 total
includes taxes & fees
Oct 14 - Oct 15
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.
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Top Middlebury Hotel Reviews

Super 8 by Wyndham Shipshewana

Super 8 by Wyndham Shipshewana

8/10 Good
"It’s good breakfast and clean"
Marvin 1-night trip
Posted 7 hours ago
Super 8 by Wyndham Shipshewana

Find out more about Middlebury

Middlebury Vacation Homes information

Number of reviews
714
Accommodation
245 Vacation Homes
Lowest Price
CA $206
Highest Price
CA $674

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