Photo by Ann Sair

Search Middlebury Cottage Rentals from CA $87

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Check prices for these dates

Next weekend
Feb 14 - Feb 16
In two weeks
Feb 21 - Feb 23
In one month
Mar 7 - Mar 9
In two months
Apr 4 - Apr 6

Browse Select Middlebury Cottages

Carefree Cottage on the Lake
Miscellaneous

Carefree Cottage on the Lake

10.0 out of 10, Exceptional, (181)
"Rented this lovely little lake house for my partner's birthday weekend!! It was beautiful and clean. Loved the spacious and well stocked kitchen, the couches are comfy, and the shower is divine!! "
Carefree Cottage on the Lake
Charming 3-bedroom cottage on fabulous Diamond Lake! Just remodeled! WiFi & AC
Living area

Charming 3-bedroom cottage on fabulous Diamond Lake! Just remodeled! WiFi & AC

2.0 star property
9.0 out of 10, Wonderful, (2)
"We had a wonderful weekend at Stacey’s home. The place was clean, spacious and well stocked with everything we needed to cook and grill. The lawn was great and right on a shallow sandy swim area. Beds were very comfortable. The hosts were very responsive answering all of our questions, and check in was very easy. Great spot overall on Diamond Lake! "
Charming 3-bedroom cottage on fabulous Diamond Lake! Just remodeled! WiFi & AC
Cozy little lake cottage on Buck Lake!
Fridge, microwave, oven, stovetop

Cozy little lake cottage on Buck Lake!

10.0 out of 10, Exceptional, (7)
"I Very much enjoyed my stay. I enjoyed hiking at the nearby park and going out on the lake on one of the kayaks. I spent most of my time on the porch enjoying the view and the peace. It was a perfect getaway."
The price is CA $291
CA $426 total
includes taxes & fees
Feb 4 - Feb 5
Cozy little lake cottage on Buck Lake!
Couples Hideaway, Private, Coziness, Country, Hygge.
Smart TV, DVD player, books, video library

Couples Hideaway, Private, Coziness, Country, Hygge.

10.0 out of 10, Exceptional, (50)
"We only stayed for one night, but it the bungalow was beautiful and very clean! We enjoyed the evening by the campfire!"
The price is CA $221
CA $361 total
includes taxes & fees
Feb 4 - Feb 5
Couples Hideaway, Private, Coziness, Country, Hygge.
Cheerful Cottage Nestled on Beautiful Witmer Lake
Property grounds

Cheerful Cottage Nestled on Beautiful Witmer Lake

9.8 out of 10, Exceptional, (17)
"The cottage was clean and nice. Easy access to parking, entry and good space for a small group to stay. The host was friendly and helpful. Easy to communicate and responsive. The additional pontoon rental availability was great! The lake was beautiful. It met our needs perfectly!"
Cheerful Cottage Nestled on Beautiful Witmer Lake
Winter Getaway I Lake Front I HOT TUB!
Fridge, microwave, oven, stovetop

Winter Getaway I Lake Front I HOT TUB!

10.0 out of 10, Exceptional, (5)
"This lake house is super clean, tastefully decorated and well appointed. The kitchen has everything you need to prepare and serve meals, and the cookware is quality. It’s the little things that make a big difference to us when we travel because it shows that the host cares about the guests. The fireplace is very cozy to sit and read or watch TV. The bed is comfortable and sleeps well. Of course the view of the lake is the highlight. We want to come back in summer so we can really enjoy the deck...
Winter Getaway I Lake Front I HOT TUB!
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, (19)
"Had a wonderful week at the lake! The house was very comfortable & clean! We enjoyed the lake and the boat. This was our second year staying here."
Very Clean Lakefront Home with Sandy Beach and Clear water.
Idyllic Lake Cottage on Papakeechie Lake
Exterior

Idyllic Lake Cottage on Papakeechie Lake

10.0 out of 10, Exceptional, (32)
"Just what we needed for a peaceful and relaxing long weekend. Can’t wait to come back!"
Idyllic Lake Cottage on Papakeechie Lake
Live & Love Life on the Lake at Sunset Cottage!
Beach

Live & Love Life on the Lake at Sunset Cottage!

9.6 out of 10, Exceptional, (37)
"We were only there during the night and gone before the sun came up but it was a nice place to stay and will try to book again when we come back "
The price is CA $131
CA $332 total
includes taxes & fees
Feb 4 - Feb 5
Live & Love Life on the Lake at Sunset Cottage!
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (6)
"The property was very clean. Cottage was in excellent shape. The property owner was VERY nice and quick on replying. It was out in the country but close to Middlebury and Shipshewana. Definitely will stay again when we come back up."
The price is CA $160
CA $202 total
includes taxes & fees
Feb 4 - Feb 5
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Be Our Guest-House on Lewis Lake
Miscellaneous

Be Our Guest-House on Lewis Lake

10.0 out of 10, Exceptional, (41)
"My daughter and I needed some quiett time and thoroughly enjoyed our stay. It was nice to cook out each night, spend some time on the lake and had coffee and fires down by the lake. The home was just perfect for two people. "
Be Our Guest-House on Lewis Lake
Waterfront Syracuse Home w/ Patio & Fire Pit!
Outdoor dining

Waterfront Syracuse Home w/ Patio & Fire Pit!

10.0 out of 10, Exceptional, (17)
"Great job of space utilization! Kitchen cabinets well organized… easy to access utensils. Everything looked brand new…. Were we the first guests?!? Enjoyed the stay immensely. 🤔Pillows were way too hard!! Sorry. Jay"
Waterfront Syracuse Home w/ Patio & Fire Pit!
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, (18)
"We loved the place the only negative is there was no blinds or curtains in the living room"
beautiful cottage by the lake. Relax and enjoy your stay.
Charming Lakefront Cottage
Property grounds

Charming Lakefront Cottage

10.0 out of 10, Exceptional, (9)
"The cottage was perfect for our family. Clean, cozy and the views of the sunset are incredible! Would highly recommend, we will be back! "
Charming Lakefront Cottage
Rome City Waterfront Oasis w/ Beach & Dock!
Interior

Rome City Waterfront Oasis w/ Beach & Dock!

9.6 out of 10, Exceptional, (21)
"Was a nice place to stay. Would like to go back some time when its a little warmer."
Rome City Waterfront Oasis w/ Beach & Dock!
Cozy Amish Country Cabin on Shipshewana Lake!
Exterior

Cozy Amish Country Cabin on Shipshewana Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
Cozy Amish Country Cabin on Shipshewana Lake!
The Wellington Cottage
Family Cottage, 3 Bedrooms, Non Smoking, Lake View | Lake view

The Wellington Cottage

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is CA $87
CA $155 total
includes taxes & fees
Feb 16 - Feb 17
The Wellington Cottage
Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!
Terrace/patio

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

10.0 out of 10, Exceptional, (2)
"Cute house to stay for our family’s annual fall trip to Michigan. Loved the location, the house was clean and the owners provided most of our essentials, also nicely decorated. Loved the covered porch for reading while My husband and the girls went kayaking. Corey Orchard is a must. Hot tub was a wonderful place to unwind from the day! "
Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!
River Retreat W/ HOT TUB/ Game room
Fridge, microwave, oven, stovetop

River Retreat W/ HOT TUB/ Game room

10.0 out of 10, Exceptional, (26)
"Nice place on the river. Comfortable and spacious. A few bad things, a few feet off a main road and vehicle noise. A salvage yard literally across the street, no screens on the windows so cant open due to bugs."
River Retreat W/ HOT TUB/ Game room
Lake Wawasee Pet-Friendly Cottage with Pontoon, Firepit, 3 decks, large lot
Outdoor dining

Lake Wawasee Pet-Friendly Cottage with Pontoon, Firepit, 3 decks, large lot

9.6 out of 10, Exceptional, (24)
"We really enjoyed this property and our stay. Easy access to lake and sandbar. The property is so well provisioned, it made the stay even better than we expected! Would totally stay again!"
Lake Wawasee Pet-Friendly Cottage with Pontoon, Firepit, 3 decks, large lot
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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Other property types in Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (6)
"The property was very clean. Cottage was in excellent shape. The property owner was VERY nice and quick on replying. It was out in the country but close to Middlebury and Shipshewana. Definitely will stay again when we come back up."
The price is CA $160
CA $202 total
includes taxes & fees
Feb 4 - Feb 5
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
Outdoor dining

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

10.0 out of 10, Exceptional, (9)
"Cabin on Stone Lake had a spectacular view. Was clean and stocked with everything needed for a comfortable stay. We had tickets for NOTRE DAME football. This cabin was only 30 min away, an easy drive. Hope to return in the summer to enjoy the lake."
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Smart TV, books

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

10.0 out of 10, Exceptional, (14)
"Very convenient location, close to the toll road. Very clean house, beautiful country setting. We would recommend this to anyone."
The price is CA $182
CA $453 total
includes taxes & fees
Feb 9 - Feb 10
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
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.

Frequently asked questions

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What is there to do in Middlebury near my cottage?
The perfect travel accessory is a well-thought-out travel plan. Deutsch Kase Haus is an excellent place to start your adventures in Middlebury.