A log cabin with red shutters and a small porch.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Middlebury cottages

Exterior

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, (68 reviews)
"Excellent place to stay, planning on staying again when we come to visit family. "
United States
Cara B.
$175 nightly
The price is $187
Sep 6 - Sep 7
Total with taxes and fees
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Terrace/patio

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
$174 nightly
The price is $200
Sep 10 - Sep 11
Total with taxes and fees
The Wellington Cottage
Outdoor dining

3. 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, (74 reviews)
"Nice for a short visit."
United States
Bob W.
$238 nightly
The price is $274
Sep 7 - Sep 8
Total with taxes and fees
Live & Love Life on the Lake at Sunset Cottage!
Exterior

4. 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.
$521 nightly
The price is $558
Sep 7 - Sep 8
Total with taxes and fees
Arrowhead Riverfront! Beautiful, Peaceful, Private
Outdoor dining

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

Lakefront Michigan Cottage - Deck, Grill & Kayaks!
Sturgis
9.4 out of 10, Exceptional, (16 reviews)
"Perfect place, nicely furnished!"
United States
Michelle n.
$450 nightly
The price is $474
Sep 30 - Oct 1
Total with taxes and fees
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
Property grounds

6. Cozy little lake cottage on Buck Lake!

Cozy little lake cottage on Buck Lake!
Vandalia
9.8 out of 10, Exceptional, (25 reviews)
"Charming cabin, quiet lake when we were there."
United States
Rebecca K.
$271 nightly
The price is $271
Sep 7 - Sep 8
Total with taxes and fees
Cozy little lake cottage on Buck Lake!
Exterior

7. 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, (87 reviews)
"Such a great stay! We very much enjoyed the cabin and recommend for a relaxing, peaceful trip."
United States
Natalie C.
$246 nightly
The price is $256
Sep 29 - Sep 30
Total with taxes and fees
Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife
Cottage (4 Bedrooms) | Interior

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

Lakefront Michigan Cottage - Deck, Grill & Kayaks!
3.0 star property
Sturgis
$444 nightly
The price is $470
Sep 30 - Oct 1
Total with taxes and fees
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
Exterior

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.
$308 nightly
The price is $345
Sep 6 - Sep 7
Total with taxes and fees
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
Property grounds

10. Diamond Lake Island Cabin

Diamond Lake Island Cabin
Cassopolis
9.0 out of 10, Wonderful, (49 reviews)
"House and property had everything we needed for a perfect weekend on the water. Would def stay again. "
United States
Nick P.
$396 nightly
The price is $396
Sep 7 - Sep 8
Total with taxes and fees
Diamond Lake Island Cabin
Outdoor dining

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

Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
North Webster
$602 nightly
The price is $675
Oct 1 - Oct 2
Total with taxes and fees
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
House (2 Bedrooms) | Interior

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

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
$251 nightly
The price is $266
Sep 9 - Sep 10
Total with taxes and fees
Cassopolis Cabin, Little Fish Lake On-site!
House (2 Bedrooms) | Interior

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

Pet-friendly Cassoplis Cabin, Close to Parks!
3.0 star property
Cassopolis
$270 nightly
The price is $286
Sep 9 - Sep 10
Total with taxes and fees
Pet-friendly Cassoplis Cabin, Close to Parks!
House (2 Bedrooms) | Interior

14. Cozy Cassopolis Cabin, Near Parks & Golfing!

Cozy Cassopolis Cabin, Near Parks & Golfing!
3.0 star property
Cassopolis
$270 nightly
The price is $286
Sep 9 - Sep 10
Total with taxes and fees
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

Van Buren Hotel

Van Buren Hotel

10/10 Excellent
"Great room. Clean. Friendly staff. Relaxing"
Jacqueline 1-night trip
Posted less than an hour ago
Van Buren Hotel

Find out more about Middlebury

Middlebury Cottages information

Number of reviews
299
Accommodation
108 Cottages
Lowest Price
$187
Highest Price
$675

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