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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 84 Cottages in Middlebury with updated reviews, rates, and availability.

Carefree Cottage on the Lake
Property grounds

Carefree Cottage on the Lake

10.0 out of 10, Exceptional, (178)
"Absolutely beautiful!!!! Can't wait to go back,"
Carefree Cottage on the Lake
Live & Love Life on the Lake!
Beach

Live & Love Life on the Lake!

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 AED 367
AED 876 total
includes taxes & fees
1 Jan - 2 January 2025
Live & Love Life on the Lake!
Relax on Klinger Lake in Summer or come to ski in Winter
Terrace/patio

Relax on Klinger Lake in Summer or come to ski in Winter

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 2,986 total
includes taxes & fees
6 Jan - 7 January 2025
Relax on Klinger Lake in Summer or come to ski in Winter
Cheerful Cottage Nestled on Beautiful Witmer Lake
Private kitchen

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
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
Sturgis Vacation Rental | 4BR | 1.5BA | 1,761 Sq Ft | Stairs Required for Access

Lakefront Michigan Cottage - Deck, Grill & Kayaks!

9.6 out of 10, Exceptional, (4)
"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!
Very Clean Lakefront Home with Sandy Beach and Clear water.
Long Lake

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.
Pleasant Lake Inlet Cottage Winter Retreat w/ Dome
Outdoor dining

Pleasant Lake Inlet Cottage Winter Retreat w/ Dome

10.0 out of 10, Exceptional, (14)
"We enjoyed a lovely Thanksgiving Weekend in this cozy cottage on Pleasant Lake. We enjoyed holiday movies and card games by the fire. The swans on the lake provide lots of birdwatching opportunities. The kitchen is well equipped and large enough to spend a happy afternoon creating a holiday feast. Thank you so much to Mike and Colleen for accommodating us!"
Pleasant Lake Inlet Cottage Winter Retreat w/ Dome
The Hilltop Hideaway lakeside Cottage- HOT TUB
The view

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
Rome City Waterfront Oasis w/ Beach & Dock!
Rome City Vacation Rental | 1BR | 1BA | 1 Step Required for Access | 842 Sq Ft

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!
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
Couples Hideaway, Private, Coziness, Country, Hygge.
King size bed, plenty of blankets and pillows

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 463
AED 806 total
includes taxes & fees
8 Jan - 9 January 2025
Couples Hideaway, Private, Coziness, Country, Hygge.
beautiful cottage by the lake. Relax and enjoy your stay.
Exterior

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
Terrace/patio

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
Property grounds

Charming Lake Cottage! Close to Shipshewana, Clean Lake, Boat Rentals

9.6 out of 10, Exceptional, (39)
"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!
Syracuse Vacation Rental | 2BR | 1BA | 672 Sq Ft | Step-Free Access

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!
River Retreat W/ HOT TUB/ Game room
Stunning views from the hot tub!

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
Charming Lakefront Cottage
Exterior

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!
Bedroom - king bed

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 507
AED 823 total
includes taxes & fees
7 Jan - 8 January 2025
Cozy little lake cottage on Buck Lake!
Lake Wawasee Pet-Friendly Cottage with Pontoon, Firepit, 3 decks, large lot
Lake Cottage

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
Unique Lakeside Retreat with Pedal Boat for a Relaxed, Pet-Friendly Getaway!
Living area

Unique Lakeside Retreat with Pedal Boat for a Relaxed, Pet-Friendly Getaway!

9.8 out of 10, Exceptional, (13)
"My wife was wanting to visit Shipshewana, so I did a search on VRBO and found this cabin. It is only a few minutes from Shipshewana, and like the listing says, it is right on the North Twin Lake. There are quite a few other houses/cabins around, but it was very quiet while we were there. I'm guessing that it is because it was off season. Did some peddling around the lake on the boat that was provided, but most of our time was just relaxing either inside the cabin or on the back deck. It don't...
Unique Lakeside Retreat with Pedal Boat for a Relaxed, Pet-Friendly Getaway!
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
Sign in
Sign up, it's free

Other property types in Middlebury

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

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
Terrace/patio

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 459
AED 1,132 total
includes taxes & fees
6 Jan - 7 January 2025
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Welcome to your Home Away From Home! Beautiful backyard and hot tub! Can't you see yourself relaxing the evening away?

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (47)
"This is a great place to stay! We loved the communication and willingness to work to make our stay the best it could be. The care and planning it takes to make this experience great show how much this property owner cares. "
The price is AED 807
AED 1,284 total
includes taxes & fees
18 Jan - 19 January 2025
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
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.