A log cabin with red shutters and a small porch.

Middlebury Vacation Rentals

Check prices for these dates

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

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)
"Great location"
United States
Tracy C.
The price is CA $195
CA $388 total
includes taxes & fees
Nov 1 - Nov 2
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 $365 total
includes taxes & fees
Oct 20 - Oct 21
| 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.
The price is CA $142
CA $343 total
includes taxes & fees
Oct 20 - Oct 21
| 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 CA $170
CA $385 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $193
CA $479 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is CA $330
CA $556 total
includes taxes & fees
Oct 28 - Oct 29
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
The price is CA $164
CA $362 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $131
CA $347 total
includes taxes & fees
Oct 22 - Oct 23
Natural Nook | Tiny Home #2 in Amish Country!
A lakeside seating area with Adirondack chairs and a canoe, surrounded by a grassy area and a large tree.

9. 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.
The price is CA $154
CA $426 total
includes taxes & fees
Oct 25 - Oct 26
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.

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 $200
CA $376 total
includes taxes & fees
Oct 21 - Oct 22
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, (331 reviews)
"Great place to stay"
United States
Joshua H.
The price is CA $191
CA $280 total
includes taxes & fees
Nov 1 - Nov 2
Millie's Cottage
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 CA $352
CA $561 total
includes taxes & fees
Oct 25 - Oct 26
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
A modern building with a sloped roof, a wooden porch, and a small outdoor seating area.

13. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Hearthstone Hideaway #5 | Shewana Tiny Home Village
Shipshewana
9.6 out of 10, Exceptional, (9 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
Oct 20 - Oct 21
Hearthstone Hideaway #5 | Shewana Tiny Home Village
A kitchenette with a coffee maker, a mug, a bowl, and a shelf with coffee containers.

14. 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
The price is CA $332
CA $623 total
includes taxes & fees
Oct 20 - Oct 21
Songbird Haven, 3 min from town, Pumpkinvine, MEC,concerts. 3 bedroom, 2 bath.
A two-story building with a wooden facade and a metal roof, featuring a porch with chairs and a small garden area.

15. 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 CA $131
CA $349 total
includes taxes & fees
Oct 29 - Oct 30
Serene Sanctuary | Tiny Home #1 in Amish Country!
A modern kitchen with white cabinets, a stainless steel refrigerator, and a wooden dining table with bar stools.

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

Kayaks | Relax by River | 10 Min to Shipshewana |
Howe
10.0 out of 10, Exceptional, (30 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 CA $142
CA $303 total
includes taxes & fees
Oct 20 - Oct 21
Kayaks | Relax by River | 10 Min to Shipshewana |
Exterior

17. 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 CA $650
CA $958 total
includes taxes & fees
Oct 20 - Oct 21
Hilltop Family Retreat
A modern kitchen with a marble countertop, a built-in oven, and a ceiling fan.

18. Whispering Cottage #3 | Shewana Tiny Home Village

Whispering Cottage #3 | Shewana Tiny Home Village
Shipshewana
9.2 out of 10, Wonderful, (12 reviews)
"Very awesome place. A bit overpriced but still a good deal and experience."
United States
Edward D.
The price is CA $131
CA $300 total
includes taxes & fees
Oct 20 - Oct 21
Whispering Cottage #3 | Shewana Tiny Home Village
The bedroom has a queen sized bed, electric fireplace, and TV for cozy, restful evenings

19. 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)
"This place was amazing! The animals in the back were a bonus. The only thing we could think to make it better was a full length mirror. Would recommend to all our family and friends to stay here!"
United States
Cindy T.
The price is CA $131
CA $347 total
includes taxes & fees
Oct 20 - Oct 21
Simple Serenity Loft | Tiny Home #6 in Amish Country!
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 $165
CA $463 total
includes taxes & fees
Oct 25 - Oct 26
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

Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

10/10 Excellent
"We enjoyed our stay very much. The room was very clean and the beds were comfortable."
Deborah 1-night trip
Posted 2 hours ago
Farmstead Inn & Conference Center

Find out more about Middlebury

Middlebury Vacation Homes information

Number of reviews
754
Accommodation
241 Vacation Homes
Lowest Price
CA $280
Highest Price
CA $958

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