A log cabin with red shutters and a small porch.

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Middlebury cottages

A wooden deck with a view of a calm lake, a dock, and a boat.

1. The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (13 reviews)
"Enjoyed our 2- night stay here."
United States
Phil
The price is ￥14,452
￥17,538 total
includes taxes & fees
Nov 16 - Nov 17
The Wellington Cottage
A single-story house with a garage, a dirt driveway, and a grassy hill in the background.

2. 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, (77 reviews)
"This host was very easy to communicate with and allowed us an early check in. Great accommodations…we’d go back for sure!"
United States
Dorothy P.
The price is ￥27,151
￥31,615 total
includes taxes & fees
Nov 15 - Nov 16
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
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, (9 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 ￥29,754
￥66,527 total
includes taxes & fees
Nov 17 - Nov 18
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, (82 reviews)
"Close commute to Shipshewana, beautiful water view,"
United States
Debra
The price is ￥16,530
￥37,744 total
includes taxes & fees
Nov 15 - Nov 16
Live & Love Life on the Lake at Sunset Cottage!
A wooden deck with a hot tub, surrounded by a metal railing, overlooking a lake with trees and a cloudy sky.

5. River Retreat W/ HOT TUB/ Game room

River Retreat W/ HOT TUB/ Game room
Bristol
10.0 out of 10, Exceptional, (34 reviews)
"Fantastic property right on the St. Joseph river. Awesome kayaking."
United States
zach d.
The price is ￥87,940
￥137,209 total
includes taxes & fees
Nov 21 - Nov 22
River Retreat W/ HOT TUB/ Game room
A rustic cabin with a wooden staircase, surrounded by lush greenery and flowering bushes.

6. 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, (93 reviews)
"Perfect stay!"
United States
Bill R.
The price is ￥19,676
￥32,835 total
includes taxes & fees
Nov 17 - Nov 18
Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife
A wooden deck with outdoor furniture, a railing, and a view of trees and a building.

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

Pet-friendly Cassoplis Cabin, Close to Parks!
3.0 star property
Cassopolis
The price is ￥30,345
￥45,628 total
includes taxes & fees
Nov 17 - Nov 18
Pet-friendly Cassoplis Cabin, Close to Parks!
A covered outdoor area with a green artificial turf floor, white railing, and a glass door leading to an interior space.

8. Cozy little lake cottage on Buck Lake!

Cozy little lake cottage on Buck Lake!
Vandalia
9.8 out of 10, Exceptional, (28 reviews)
"Charming cabin, quiet lake when we were there."
United States
Rebecca K.
The price is ￥23,717
￥36,813 total
includes taxes & fees
Nov 16 - Nov 17
Cozy little lake cottage on Buck Lake!
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
9.4 out of 10, Exceptional, (20 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is ￥29,387
￥53,305 total
includes taxes & fees
Nov 15 - Nov 16
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
A covered patio with wicker furniture, a glass table, and hanging plants.

10. Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
North Webster
The price is ￥33,101
￥92,941 total
includes taxes & fees
Nov 23 - Nov 24
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
A wooden deck with a table and chairs, surrounded by a wooden railing, overlooking a grassy area with trees.

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

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
The price is ￥30,345
￥42,521 total
includes taxes & fees
Nov 17 - Nov 18
Cassopolis Cabin, Little Fish Lake On-site!
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 ￥30,345
￥45,628 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Cassopolis Cabin, Near Parks & Golfing!
A two-story house with a covered porch, a front door, and a small front yard with shrubs.

13. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
3.0 star property
Syracuse
The price is ￥28,748
￥75,961 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront Family Gem w/ Private Dock in Syracuse
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

Van Buren Hotel

Van Buren Hotel

8/10 Good
"The hotel was nice. Breakfast was good. Plenty of variety. The beds were clean. The room was clean, but the mattresses themselves were very, very lumpy and uncomfortable. I’m still having back pain from sleeping on the lumpy bed."
Lorrey 1-night trip
Posted less than an hour ago
Van Buren Hotel

Find out more about Middlebury

Middlebury Cottages information

Number of reviews
274
Accommodation
107 Cottages
Lowest Price
￥17,538
Highest Price
￥137,209

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