A log cabin with red shutters and a small porch.

Holiday Homes in Middlebury

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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, (73 reviews)
"This is a great Property!"
United States
Patrick B.
The price is AU$386
includes taxes & fees
13 Sept - 14 Sept
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 AU$387
includes taxes & fees
14 Sept - 15 Sept
| Hot Tub | Amish Farm Country | Pergola | Deck |
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

3. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is AU$423
includes taxes & fees
14 Sept - 15 Sept
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.

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, (32 reviews)
"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."
United States
Dianna D.
The price is AU$441
includes taxes & fees
13 Sept - 14 Sept
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.

5. Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is AU$469
includes taxes & fees
16 Sept - 17 Sept
Hidden Log Cabin Hot Tub Ping Pong Family
A lakeside seating area with Adirondack chairs and a canoe, surrounded by a grassy area and a large tree.

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

Lake House | Shallow Sandy | Kayaks | Family Fun
Middlebury
9.8 out of 10, Exceptional, (10 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 AU$435
includes taxes & fees
13 Sept - 14 Sept
Lake House | Shallow Sandy | Kayaks | Family Fun
A two-story building with a wooden facade and a metal roof, featuring a porch with chairs and a small garden area.

7. 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 AU$348
includes taxes & fees
14 Sept - 15 Sept
Serene Sanctuary | Tiny Home #1 in Amish Country!
A house with a porch, a window with a flower box, and a chair outside.

8. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (319 reviews)
"Great property. Good location. Would stay again."
United States
BigJohnsCards24
The price is AU$295
includes taxes & fees
17 Sept - 18 Sept
Millie's Cottage
A spacious living room with a wooden dining table, chairs, a television, and a large window with curtains.

9. Lake House Shallow Sandy Kayaks Family Fun

Lake House Shallow Sandy Kayaks Family Fun
2.0 star property
Shipshewana
The price is AU$495
includes taxes & fees
13 Sept - 14 Sept
Lake House Shallow Sandy Kayaks Family Fun
A two-story house with a front porch, a grill, and a door with a wreath.

10. Beautiful Private Setting !!!

Beautiful Private Setting !!!
Bristol
10.0 out of 10, Exceptional, (29 reviews)
"Great setting and well supplied. "
United States
Audrey H.
The price is AU$566
includes taxes & fees
26 Sept - 27 Sept
Beautiful Private Setting !!!
A kitchen with a coffee maker, a coffee mug rack, and a view of a lake through a window.

11. Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax

Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
Shipshewana
Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
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.

12. 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 AU$206
includes taxes & fees
13 Sept - 14 Sept
The Gemini
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, (49 reviews)
"We had a great stay!!"
United States
Sally F.
The price is AU$424
includes taxes & fees
15 Sept - 16 Sept
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
A spacious loft with a stone fireplace, large windows, and a cozy seating area.

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

Riverhaven! Glamorous A-Frame on St Joe River!
Bristol
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful place to stay! The home was very clean and the location was perfect!"
United States
Emmajo R.
The price is AU$938
includes taxes & fees
15 Sept - 16 Sept
Riverhaven! Glamorous A-Frame on St Joe River!
A porch with a sign reading "EMMAS PLACE" and an American flag.

15. Emma's Place

Emma's Place
LaGrange
9.8 out of 10, Exceptional, (74 reviews)
"Inside very clean. Nice neighborhood. Would stay again"
United States
Kenny M.
The price is AU$481
includes taxes & fees
14 Sept - 15 Sept
Emma's Place
A view from a balcony overlooking a frozen lake with bare trees and a clear sky.

16. 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, (47 reviews)
"Lovely place to stay and so close to water. "
United States
Ron O.
The price is AU$487
includes taxes & fees
14 Sept - 15 Sept
Live & Love Life on the Lake at Sunset Peak!

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 AU$940
includes taxes & fees
14 Sept - 15 Sept
Hilltop Family Retreat
A cozy living room with a sofa, two rocking chairs, a coffee table, and a ceiling fan. A sliding glass door leads to a balcony.

18. Peaceful riverfront home, 3 bedroom, sleeps 6, in Elkhart.

Peaceful riverfront home, 3 bedroom, sleeps 6, in Elkhart.
Elkhart
The price is AU$683
includes taxes & fees
13 Sept - 14 Sept
Peaceful riverfront home, 3 bedroom, sleeps 6, in Elkhart.
A cozy seating area with wicker chairs and a teal rug, a 'Welcome to our Lake House' sign, and nautical decorations.

19. 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 AU$471
includes taxes & fees
14 Sept - 15 Sept
Lake Front Cottage Kayaks Game Table Fun
A wooden deck with a view of a lake, a covered seating area, and a building with a window.

20. 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
7.0 out of 10, Good, (2 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 AU$746
includes taxes & fees
14 Sept - 15 Sept
Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa
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

Blue Gate Garden Inn

Blue Gate Garden Inn

8/10 Good
"Internet wasn't the best and the tv signal went out a couple times. We weren't there for that so the overall experience was good."
Kenneth 2-night trip
Posted 4 hours ago
Blue Gate Garden Inn

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