A log cabin with red shutters and a small porch.

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Check prices for these dates

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

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, (75 reviews)
"Excellent place to stay, planning on staying again when we come to visit family. "
United States
Cara B.
The price is €157
includes taxes & fees
22 Oct - 23 Oct
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, (11 reviews)
"Enjoyed our 2- night stay here."
United States
Phil
The price is €106
includes taxes & fees
1 Nov - 2 Nov
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, (7 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 €465
includes taxes & fees
26 Oct - 27 Oct
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, (78 reviews)
"Close commute to Shipshewana, beautiful water view,"
United States
Debra
The price is €240
includes taxes & fees
26 Oct - 27 Oct
Live & Love Life on the Lake at Sunset Cottage!
A rustic cabin with a wooden staircase, surrounded by lush greenery and flowering bushes.

5. 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, (90 reviews)
"Perfect stay!"
United States
Bill R.
The price is €242
includes taxes & fees
26 Oct - 27 Oct
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.

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

Pet-friendly Cassoplis Cabin, Close to Parks!
3.0 star property
Cassopolis
The price is €254
includes taxes & fees
28 Oct - 29 Oct
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.

7. 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 €223
includes taxes & fees
27 Oct - 28 Oct
Cozy little lake cottage on Buck Lake!
A black single-story house with a red roof, a covered patio, and a small garden area.

8. 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, (19 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is €313
includes taxes & fees
22 Oct - 23 Oct
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.

9. 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 €513
includes taxes & fees
17 Nov - 18 Nov
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
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 €237
includes taxes & fees
28 Oct - 29 Oct
Cassopolis Cabin, Little Fish Lake On-site!
A wooden deck with outdoor furniture, a railing, and a view of trees and a cloudy sky.

11. Cozy Cassopolis Cabin, Near Parks & Golfing!

Cozy Cassopolis Cabin, Near Parks & Golfing!
3.0 star property
Cassopolis
The price is €255
includes taxes & fees
28 Oct - 29 Oct
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

Blue Gate Garden Inn

Blue Gate Garden Inn

8/10 Good
"We love staying at the Bluegate. The hotel is great and the breakfast is especially good. The room we stayed in did have a water spot on the ceiling and the mattress needed to be replaced. Otherwise, a great place to stay!"
Mark 1-night trip
Posted less than an hour ago
Blue Gate Garden Inn

Find out more about Middlebury

Middlebury Cottages information

Number of reviews
308
Accommodation
107 Cottages
Lowest Price
€106
Highest Price
€513

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 favourite with locals and tourists alike.