A log cabin with red shutters and a small porch.

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middlebury cottages

A single-story house with a garage, a dirt driveway, and a grassy hill in the background.

1. Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury
10.0 out of 10, Exceptional, (70 reviews)
"Excellent place to stay, planning on staying again when we come to visit family. "
United States
Cara B.
The price is ￥24,399
￥29,475 total
includes taxes & fees
Oct 1 - Oct 2
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
A waterfront view with an American flag, a boat, and a sunset.

2. The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (9 reviews)
"Easy 10/10 recommendation Perfect place for peace"
United States
Bonala
The price is ￥18,275
￥21,922 total
includes taxes & fees
Oct 11 - Oct 12
The Wellington Cottage
A two-story house with a balcony, surrounded by a well-maintained lawn and trees.

3. Arrowhead Riverfront! Beautiful, Peaceful, Private

Arrowhead Riverfront! Beautiful, Peaceful, Private
Bristol
10.0 out of 10, Exceptional, (3 reviews)
"This was a lovely location, quiet and relaxing, for a visit with our family from Elkhart. It has plenty of room, a well-stocked kitchen, and was very clean. It’s close to a grocery store and several small towns that we like to visit."
United States
Dawn W.
The price is ￥36,692
￥75,978 total
includes taxes & fees
Oct 4 - Oct 5
Arrowhead Riverfront! Beautiful, Peaceful, Private
A covered patio with a table, chairs, a grill, and a view of a lake at sunset.

4. Live & Love Life on the Lake at Sunset Cottage!

Live & Love Life on the Lake at Sunset Cottage!
Howe
9.6 out of 10, Exceptional, (76 reviews)
"Nice for a short visit."
United States
Bob W.
The price is ￥17,709
￥40,097 total
includes taxes & fees
Oct 5 - Oct 6
Live & Love Life on the Lake at Sunset Cottage!
A two-story house with a deck, large windows, and a white exterior.

5. Lakefront Michigan Cottage - Deck, Grill & Kayaks!

Lakefront Michigan Cottage - Deck, Grill & Kayaks!
Sturgis
9.6 out of 10, Exceptional, (17 reviews)
"Perfect place, nicely furnished!"
United States
Michelle n.
The price is ￥24,241
￥73,649 total
includes taxes & fees
Sep 30 - Oct 1
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
A covered outdoor area with a green artificial turf floor, white railing, and a glass door leading to an interior space.

6. Cozy little lake cottage on Buck Lake!

Cozy little lake cottage on Buck Lake!
Vandalia
9.8 out of 10, Exceptional, (27 reviews)
"Charming cabin, quiet lake when we were there."
United States
Rebecca K.
The price is ￥26,067
￥38,660 total
includes taxes & fees
Oct 6 - Oct 7
Cozy little lake cottage on Buck Lake!
A two-story house with a deck, large windows, and a white exterior.

7. Lakefront Michigan Cottage - Deck, Grill & Kayaks!

Lakefront Michigan Cottage - Deck, Grill & Kayaks!
3.0 star property
Sturgis
The price is ￥31,299
￥73,966 total
includes taxes & fees
Sep 30 - Oct 1
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
A rustic cabin with a wooden staircase, surrounded by lush greenery and flowering bushes.

8. Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife

Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife
Vandalia
10.0 out of 10, Exceptional, (89 reviews)
"Such a great stay! We very much enjoyed the cabin and recommend for a relaxing, peaceful trip."
United States
Natalie C.
The price is ￥24,913
￥38,990 total
includes taxes & fees
Oct 7 - Oct 8
Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife
A black single-story house with a red roof, a covered patio, and a small garden area.

9. Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
Syracuse
9.6 out of 10, Exceptional, (17 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is ￥28,963
￥51,832 total
includes taxes & fees
Sep 30 - Oct 1
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
A wooden deck with outdoor furniture, a railing, and a view of trees and a building.

10. Cassopolis Cabin, Little Fish Lake On-site!

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
The price is ￥29,883
￥41,874 total
includes taxes & fees
Oct 4 - Oct 5
Cassopolis Cabin, Little Fish Lake On-site!
A wooden deck with outdoor furniture, a railing, and a view of trees and a building.

11. Pet-friendly Cassoplis Cabin, Close to Parks!

Pet-friendly Cassoplis Cabin, Close to Parks!
3.0 star property
Cassopolis
The price is ￥29,883
￥44,933 total
includes taxes & fees
Oct 12 - Oct 13
Pet-friendly Cassoplis Cabin, Close to Parks!
A wooden deck with outdoor furniture, a railing, and a view of trees and a cloudy sky.

12. Cozy Cassopolis Cabin, Near Parks & Golfing!

Cozy Cassopolis Cabin, Near Parks & Golfing!
3.0 star property
Cassopolis
The price is ￥29,883
￥44,933 total
includes taxes & fees
Oct 12 - Oct 13
Cozy Cassopolis Cabin, Near Parks & Golfing!
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

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

10/10 Excellent
"Everything was great."
Barbara 1-night trip
Posted 1 hour ago
Essenhaus Inn & Conference Center

Find out more about Middlebury

Middlebury Cottages information

Number of reviews
308
Accommodation
109 Cottages
Lowest Price
￥21,922
Highest Price
￥75,978

Frequently asked questions

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What is there to do in Middlebury near my cottage?
If you're eager to make the most of your time in Middlebury, make tracks to Deutsch Kase Haus. It's a favorite with locals and tourists alike.