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Vacation rentals in Middlebury

Vacation rentals in Middlebury

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middlebury

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Furnished farmhouse 2nd floor private apartment
    Entire flat · 4 guests · 2 beds · 1 bathroom
    Furnished farmhouse 2nd floor private apartment

    We have a lovely old farmhouse with a separate apt. upstairs. Private entrance. Furnished. The grounds are lovely with almost 2 acres of land. We're located on a quiet dead end street on the Waterbury / Naugatuck line. We offer off street parking. There are 2 bedrooms with plenty of closet space and a full bathroom with tub and shower. The living room is spacious with a couch and chairs and TV. There's also a private deck off of the living room. Our apt. is also listed on Furnished Finders.

    What guests are saying:

    “I can't say enough about Kim and her place! Not only is her property absolutely stunning, but she is an excellent host and amazing person. My wife fell in love with the farmhouse feel. Everything was sparkling clean and the kitchen was well stocked with everything we needed, including dishes, condiments, spices, and fresh eggs. When I told Kim my wife was allergic to pet dander she offered to vacuum and shampoo the entire unit before we arrived! We were in town to complete an infant adoption and Kim worked with us every step of the way. She was flexible, attentive, responsive, and went out of her way to make sure we had everything we needed. We HIGHLY recommend this Airbnb!!!”

  • Almosta Vineyard Farm Getaway
    SUPERHOSTFarm stay · 7 guests · 5 beds · 1 bathroom
    Almosta Vineyard Farm Getaway

    Bright rustic farmhouse with beautiful field views! Truly a one of a kind location; short walk to Quassy amusement park, short two mile drive to the center of Woodbury; which offers many great restaurants, stores, and access to the CT antique trail, walking access to the Middlebury greenway, centrally located near various hiking locations, and local to numerous wineries and breweries. Quick access to 84 and Route 8. Includes two private ponds ready to be fished and a brand new barn!

    What guests are saying:

    “Very nice, well kept, super clean, and cozy. The location is perfect and the grounds are beautiful. Can't beat the adorable neighbors (goats, pigs, and chickens). We had a great stay with comfortable beds and plenty of space. Would definitely stay here again.”

  • Lakeside Private Guest Suite
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bathroom
    Lakeside Private Guest Suite

    Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful!

    What guests are saying:

    “Jennifer and her family are incredible. She was very accommodating and very quick to respond with any questions. She was flexible with check-in and check-out time, which was extremely helpful. The place is the same as pictures and the scenery getting there was very tranquil. The place was very clean and had all of the necessities for a nights stay. Would definitely recommend!”

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Middlebury holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Holiday rentals under £118

The average cost for a stay in Middlebury is £148/night.

Furnished farmhouse 2nd floor private apartment
Entire flat
Furnished farmhouse 2nd floor private apartment
Price:£40 / night
Private Studio Apartment
Entire flat
Private Studio Apartment
Price:£23 / night
Almosta Vineyard Farm Getaway
SUPERHOSTFarm stay
Almosta Vineyard Farm Getaway
Price:£103 / night
COOL PLACE
Private room
COOL PLACE
Price:£26 / night
2br in Alladins spot
Entire flat
2br in Alladins spot
Price:£33 / night
Dale's Place
Private room
Dale's Place
Price:£34 / night
Beautiful large house w\pool for longer term stays
Private room
Beautiful large house w\pool for longer term stays
Price:£33 / night
Spacious room in renovated home in Prospect
SUPERHOSTPrivate room
Spacious room in renovated home in Prospect
Price:£28 / night
Downtown Student Single
Private room
Downtown Student Single
Price:£23 / night
Convenient business rental New Haven/Yale/Shelton
Private room
Convenient business rental New Haven/Yale/Shelton
Price:£31 / night
Spacious 2 bedroom apartment
Entire flat
Spacious 2 bedroom apartment
Price:£37 / night
Ma Petite Maison
Private room
Ma Petite Maison
Price:£40 / night
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