Photo by Ann Sair

Search Cottages in Middlebury

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 85 Cottages in Middlebury with updated reviews, rates, and availability.

Carefree Cottage on the Lake
10.0 out of 10, Exceptional, (175)
"We loved our stay at the lake house. The house is cozy, comfortable & clean & the location is so peaceful & beautiful. We have family in the area & we will definitely be back to this awesome place!"
Carefree Cottage on the Lake
Live & Love Life on the Lake!
9.6 out of 10, Exceptional, (36)
"Nice location"
The price is AED 360
AED 868 total
includes taxes & fees
21 Nov - 22 Nov
Live & Love Life on the Lake!
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 AED 404
AED 511 total
includes taxes & fees
21 Nov - 22 Nov
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Relax by the lake- enjoy wine country and ski slopes
9.0 out of 10, Wonderful, (9)
"This Host! When my head was spinning from the tragic loss of my Father—she was direct and kind! Completely understanding of the needs of our family! This Is a beautiful property; fully stocked well taken care of and very clean! I can’t thank you enough, France, for making our stay as low stress possible! 💯% recommend checking this place out💕"
The price is AED 1,462
AED 3,015 total
includes taxes & fees
20 Nov - 21 Nov
Relax by the lake- enjoy wine country and ski slopes
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
Amazing Family Getaway on All Sport Pleasant Lake -Short drive from Chi GR & DET
10.0 out of 10, Exceptional, (13)
"Our house was damaged in the May 7 Portage, MI tornado so after outside repairs were completed, we moved out for 2 weeks while they completed inside repairs. While the tornado was a tragic experience for us, to be able to spend time at this location, on the lake (the sunrise is breathtaking), with family and friends was a blessing in disguise. We also had unseasonably warm September weather the entire time so we enjoyed the lake, the paddleboat, kayaks and the boat! Working with the insurance...
Amazing Family Getaway on All Sport Pleasant Lake -Short drive from Chi GR & DET
The Hilltop Hideaway lakeside Cottage- HOT TUB
10.0 out of 10, Exceptional, (4)
"We had a great stay over Labor Day weekend and it was exactly what I was hoping for - a calm weekend away to spend with our family. The house was so cute, clean, and had everything we could have asked for. There were so many little details provided by the hosts that made us feel so comfortable. The lake was gorgeous and so peaceful. I am quite sad our trip is over! "
The Hilltop Hideaway lakeside Cottage- HOT TUB
Beautiful Cottage With Water Access and Kayaks!
10.0 out of 10, Exceptional, (10)
"Great home on the water!"
Beautiful Cottage With Water Access and Kayaks!
Howe Retreat w/ Fire Pit + Private Boat Dock!
3.0 star property
10.0 out of 10, Exceptional, (1)
"This location is great for people looking for quiet and enjoy peace! The house has lots of space and has all the amenities required. My only down side if the WiFi, as I had to work the entire week, the connection dropped almost every day, but who rents this house for working the entire week???"
Howe Retreat w/ Fire Pit + Private Boat Dock!
Quaint cozy cottage nestled on the quiet shores of Pigeon Lake in Howe
2.0 star property
10.0 out of 10, Exceptional, (5)
"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
Rome City Waterfront Oasis w/ Beach & Dock!
9.6 out of 10, Exceptional, (21)
"Lovely cottage with a beautiful view and access to the lake. Very clean property and Angie was very accommodating and communicated well. The place was nicely stocked and even had some nice touches for our toddler. "
Rome City Waterfront Oasis w/ Beach & Dock!
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
Couples Hideaway, Private, Coziness, Country, Hygge.
10.0 out of 10, Exceptional, (49)
"Clean, comfortable, quiet and cozy setting in the woods."
The price is AED 459
AED 795 total
includes taxes & fees
24 Nov - 25 Nov
Couples Hideaway, Private, Coziness, Country, Hygge.
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.
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
Charming Lake Cottage! Close to Shipshewana, Clean Lake, Boat Rentals
9.6 out of 10, Exceptional, (38)
"My wife & I thoroughly enjoyed our 27th anniversary weekend simply relaxing and enjoying the lake view. Our kids visited & an evening stroll around the lake on the pontoon. Awesome place to disconnect & relax!! us for an evening cookout on the deck and the "
Charming Lake Cottage! Close to Shipshewana, Clean Lake, Boat Rentals
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!
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
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 AED 735
AED 1,087 total
includes taxes & fees
20 Nov - 21 Nov
Cozy little lake cottage on Buck Lake!
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
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.
Don't see what you're looking for?
See all available properties in Middlebury
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middlebury

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 AED 441
AED 1,167 total
includes taxes & fees
2 Dec - 3 Dec
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (45)
"The house was beautiful! Very comfortable and welcoming. Will definitely stay here again if in the area!"
The price is AED 545
AED 1,000 total
includes taxes & fees
22 Nov - 23 Nov
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (8)
"So many stairs. Haha, it was good though. Kayaks and paddle boat were fun exercise as well. Relaxing on the top deck with the amazing view was exactly what I needed. "
Amazing view of Stone Lake from top deck. Thirty five miles from 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

Why book your cottage in Middlebury with Expedia?
Booking a cottage in Middlebury is as simple as deciding on your travel dates and choosing your ideal place for a vacation in nature. From ritzy retreats to low-cost stays and cottages that offer perks like a hot tub, Expedia has something for all tastes and styles. As for unbeatable deals? We’ve got you covered!
How can I find cheap cottages in Middlebury?
With Expedia’s useful filter tool, comparing cheap cottages in Middlebury is easy. To view accommodations that’ll make your wallet smile, refine your search by amenities, star rating and budget.