Photo by Ann Sair

Search Middlebury Cottage Rentals from CA $156

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Middlebury Cottages

Our top choices for Middlebury cottages

Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan
Outdoor dining

Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan

2.0 star property
10.0 out of 10, Exceptional, (6)
Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan
beautiful cottage by the lake. Relax and enjoy your stay.
Fridge, microwave, oven, stovetop

beautiful cottage by the lake. Relax and enjoy your stay.

9.8 out of 10, Exceptional, (22)
"Very nice, wish there was bars or restaurants on the lake"
beautiful cottage by the lake. Relax and enjoy your stay.
Quaint cozy cottage nestled on the quiet shores of Pigeon Lake in Howe
Interior

Quaint cozy cottage nestled on the quiet shores of Pigeon Lake in Howe

2.0 star property
10.0 out of 10, Exceptional, (22)
"Everything was in excellent condition. Very clean. The hostess was very nice and thought of everything. The cottage was very cozy. Perfect weekend stay!!"
Quaint cozy cottage nestled on the quiet shores of Pigeon Lake in Howe
Live & Love Life on the Lake at Sunset Cottage!
Outdoor dining

Live & Love Life on the Lake at Sunset Cottage!

9.6 out of 10, Exceptional, (50)
"Very relaxing, nice property. "
The price is CA $153
CA $354 total
includes taxes & fees
Aug 26 - Aug 27
Live & Love Life on the Lake at Sunset Cottage!
Cozy Cottage on St Joseph River in Bristol.
Exterior

Cozy Cottage on St Joseph River in Bristol.

10.0 out of 10, Exceptional, (9)
"Very comfortable and convenient place. I would stay there again!"
Cozy Cottage on St Joseph River in Bristol.
Carefree Lakefront Cottage/ 11 mins to skiing
Terrace/patio

Carefree Lakefront Cottage/ 11 mins to skiing

10.0 out of 10, Exceptional, (201)
"Hopefully we'll be able to make it back when it's warmer beautiful "
Carefree Lakefront Cottage/ 11 mins to skiing
Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet
Exterior detail

Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet

10.0 out of 10, Exceptional, (60)
"Very nice, and very clean, we enjoyed our stay "
The price is CA $199
CA $329 total
includes taxes & fees
Aug 26 - Aug 27
Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet
Cheerful Cottage Nestled on Beautiful Witmer Lake
Property grounds

Cheerful Cottage Nestled on Beautiful Witmer Lake

9.8 out of 10, Exceptional, (22)
"Very clean and comfortable. House was very well equipped with everything we needed. "
Cheerful Cottage Nestled on Beautiful Witmer Lake
Beautiful Cottage With Water Access and Kayaks!
Fridge, microwave, oven, stovetop

Beautiful Cottage With Water Access and Kayaks!

10.0 out of 10, Exceptional, (12)
"We had a great stay for a girls’ weekend on Klinger Lake. The house and outdoor deck was perfect for our needs."
Beautiful Cottage With Water Access and Kayaks!
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Microwave, oven, stovetop

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

The price is CA $254
CA $456 total
includes taxes & fees
Aug 24 - Aug 25
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi
Interior

Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi

10.0 out of 10, Exceptional, (5)
"Place is beautiful "
Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Property grounds

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

2.0 star property
10.0 out of 10, Exceptional, (24)
"Would definitely come back!"
The price is CA $159
CA $199 total
includes taxes & fees
Sep 4 - Sep 5
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Diamond Lake Island Cabin
Dining

Diamond Lake Island Cabin

9.0 out of 10, Wonderful, (37)
"Absolutely perfect weekend getaway! "
Diamond Lake Island Cabin
Cozy little lake cottage on Buck Lake!
Fridge, microwave, oven, stovetop

Cozy little lake cottage on Buck Lake!

10.0 out of 10, Exceptional, (11)
"Our stay was great! The house was very clean and had everything we needed. The location was nice and quiet, perfect for a relaxing vacation. "
The price is CA $248
CA $374 total
includes taxes & fees
Aug 21 - Aug 22
Cozy little lake cottage on Buck Lake!
Charming 4-bedroom cottage on fabulous Diamond Lake! Just remodeled! WiFi & AC
Living area

Charming 4-bedroom cottage on fabulous Diamond Lake! Just remodeled! WiFi & AC

2.0 star property
9.0 out of 10, Wonderful, (4)
"Great summer cottage! We were in the area for a wedding on the lake and it was the perfect set up. Agree with other guests to bring water shoes. The lake is amazing but does have a rocky bottom near the shoreline. House had plenty of room for our party of 7. Nice pier and we were able to rent a pontoon boat and tie off. Thanks again :)"
Charming 4-bedroom cottage on fabulous Diamond Lake! Just remodeled! WiFi & AC
Very Clean Lakefront Home with Sandy Beach and Clear water.
Interior

Very Clean Lakefront Home with Sandy Beach and Clear water.

9.4 out of 10, Exceptional, (21)
"We had a great stay! Weather was perfect, house clean & beach sandy."
Very Clean Lakefront Home with Sandy Beach and Clear water.
Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!
Terrace/patio

Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!

9.4 out of 10, Exceptional, (6)
"We left early"
Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!
Cozy Haven of Rest Home w/ Amish Country Views!
House (2 Bedrooms) | Interior

Cozy Haven of Rest Home w/ Amish Country Views!

2.0 star property
10.0 out of 10, Exceptional, (1)
"It was the most peaceful place I have ever stayed. Loved it Very clean."
Cozy Haven of Rest Home w/ Amish Country Views!
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
Terrace/patio

Lakefront Michigan Cottage - Deck, Grill & Kayaks!

9.8 out of 10, Exceptional, (8)
"We very much enjoyed our stay in your home. We had everything we needed and more. It was very clean. The beds were fantastic as were the pillows. Great quality linens. I appreciate that and a good night sleep. The home was beautiful and decorated nicely. It was wonderful having coffee in the morning with the lake right outside our window. Thank you so much for making our trip to see the Christmas lights in Shipshewana that much more memorable "
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
House (3 Bedrooms) | Interior

Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres

2.0 star property
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlebury Hotel Reviews

Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

10/10 Excellent
"Nice hotel, clean, very nice rooms"
CHRISTINE 1-night trip
Posted 13 hours ago
Farmstead Inn & Conference Center