A log cabin with red shutters and a small porch.

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Our top choices for Middlebury cottages

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 AU$171
includes taxes & fees
28 Nov - 29 Nov
The Wellington Cottage

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 AU$287
includes taxes & fees
15 Nov - 16 Nov
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

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 AU$659
includes taxes & fees
16 Nov - 17 Nov
Arrowhead Riverfront! Beautiful, Peaceful, Private

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 AU$350
includes taxes & fees
11 Nov - 12 Nov
Live & Love Life on the Lake at Sunset Cottage!

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, (92 reviews)
"Perfect stay!"
United States
Bill R.
The price is AU$323
includes taxes & fees
8 Dec - 9 Dec
Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife

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

Pet-friendly Cassoplis Cabin, Close to Parks!
3.0 star property
Cassopolis
The price is AU$413
includes taxes & fees
17 Nov - 18 Nov
Pet-friendly Cassoplis Cabin, Close to Parks!

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 AU$352
includes taxes & fees
15 Nov - 16 Nov
Cozy little lake cottage on Buck Lake!

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, (20 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is AU$472
includes taxes & fees
11 Nov - 12 Nov
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

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 AU$797
includes taxes & fees
23 Nov - 24 Nov
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

10. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
3.0 star property
Syracuse
The price is AU$687
includes taxes & fees
11 Nov - 12 Nov
Waterfront Family Gem w/ Private Dock in Syracuse

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

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
The price is AU$385
includes taxes & fees
17 Nov - 18 Nov
Cassopolis Cabin, Little Fish Lake On-site!

12. Cozy Cassopolis Cabin, Near Parks & Golfing!

Cozy Cassopolis Cabin, Near Parks & Golfing!
3.0 star property
Cassopolis
The price is AU$413
includes taxes & fees
17 Nov - 18 Nov
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

Find out more about Middlebury

Middlebury Cottages information

Number of reviews
239
Accommodation
108 Cottages
Lowest Price
AU$171
Highest Price
AU$797

Frequently asked questions

What is there to do in Middlebury near my cottage?
If you want to fill up your itinerary in Middlebury, make tracks to Wine Cellar Supply Winery. It's a hit among visitors and locals alike.