We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Middlebury Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $436 Average
    $0$1,000+
    Suitability
    More filters
    All 15 Rentals in Middlebury
    Sort by:
    Default
    Don't let other travellers get your favourite Middlebury area holiday rental. You're so close to securing your perfect getaway. Book today.
    The following rentals are within 25 kilometres of Middlebury.
    New Milford
    4 Reviews
    4 Bedrooms, Sleeps 8Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Hamden
    1 Bedroom, Sleeps 2Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Hamden
    1 Bedroom, Sleeps 3Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Woodbury
    3 Reviews
    4 Bedrooms, Sleeps 8Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 22 June 2015
    We came to Woodbury to meet as a family & acknowledge the passing of our father in the town we all grew up in. Douglas was extremely helpful and encouraging in our arranging for...
    Excellent of 5 bubbles
    Reviewed 13 June 2015
    This property is conveniently located near I84 and the restaurants/shops of Woodbury and Southbury, Conn. It is a beautiful house with a fully equipped kitchen, washer/dryer...
    See all reviews
    About this property
    This four bedroom antique, photograph, and sculpture filled, light-splashed two story home on Connecticut's Antique Trail has spacious indoor and outdoor lounging areas in a beautiful acre private garden setting three minutes from Woodbury's historic town center. Even better its only one minute...
    View all property information
    Location Information
    Woodbury, Connecticut 06798
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Southbury
    1 Review
    2 Bedrooms, Sleeps 6Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Secure Parking
    • Mountain Views
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 8 January 2015
    My husband and I, and our doggies, enjoyed the Coach House so much. We became friends with the owner who was very accomodating. He even loaned us his ornaments, so we could...
    See all reviews
    About this property
    Charming, recently renovated, two-story, 1,200 square-foot coach house built in 1795 and set in a tranquil 3-acres of lawns, gardens, orchards and forest at the heart of the historic Village of South Britain founded in 1715 by settlers from the south of England, This vacation home an hour and a...
    View all property information
    Location Information
    Southbury, Connecticut 06488
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Bethlehem
    5 Bedrooms, Sleeps 16Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Grill
    • Terrace
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Judd Farm House is situated on 33 acres, the house is in farm country. It is surrounded by rolling hills of Litchfield. There are country roads for walking and biking with very little traffic. It is a perfect retreat for a group there are generous size bedrooms tastlefully decorated. There is a...
    View all property information
    Location Information
    Bethlehem, Connecticut 06795
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
    Make Enquiry
    Bethlehem
    6 Bedrooms, Sleeps 12Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All...
    View all property information
    Location Information
    Bethlehem, Connecticut 06751
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    New Milford
    5 Bedrooms, Sleeps 10Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Garden
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1840 completely renovated country house with lots of room, convenience and quietness. 4,000 sq. ft. furnished with many antiques. A most unique country kitchen, formal dining room, eat-in kitchen, library, living room, den, five bedrooms (some have "Sleep Number" mattresses), and 5 and a half...
    View all property information
    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    Bethlehem
    5 Bedrooms, Sleeps 10Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All...
    View all property information
    Location Information
    Bethlehem, Connecticut 06751
    Private Room - 5 Bedrooms, Sleeps 10
    Make Enquiry
    Newtown
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Housekeeping Included
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A historic and charming three bedroom, two bath saltbox farmhouse on the grounds of the beautiful and private McLaughlin Vineyards. The house is conveniently located in Northern Fairfield County, about four miles from I-84 and only 90 minutes from mid-town Manhattan. With a large expansive front...
    View all property information
    Location Information
    Newtown, Connecticut 06482
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Morris
    3 Bedrooms, Sleeps 11Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront house with private sandy beach located on the West shoreline of Bantam Lake. Contemporarty A frame style house with 3 bedrooms - 2.5 baths and cozy loft area. All amenities.
    View all property information
    Location Information
    Morris, Connecticut 06763
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 11
    Make Enquiry
    Southbury
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is in a historic village with 22 others clustered around the Congregational Church across the street from the house. Built in 1795 it has four large corner rooms on both floors On the first floor there's a central entry hall, with dining and library to either side, straight ahead are...
    View all property information
    Location Information
    Southbury, Connecticut 06488
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Seymour
    1 Bedroom, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Magnificent, fully furnished 1st floor apartment of our 2 story home in one of the best areas of Seymour, CT. Our apartment is for non- smokers only. Very clean and calm. The apartment features a spacious living room with a 2 comfortable futon and one couch, a separate bedroom with queen size bed,...
    View all property information
    Location Information
    Seymour, Connecticut 06483
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    Make Enquiry
    Washington
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Street is a mint condition 4 bedroom home with a heated pool, wonderful flat private quiet yard with a swing set far back from the street. The home is in Washington, the most desirable historic rural town in Litchfield County with wonderful restaurants, land preserves, private schools,...
    View all property information
    Location Information
    Washington, Connecticut 06793
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Roxbury
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best way to experience Roxbury Connecticut... A completely Private Apartment in Modern contemporary home located on Route 67 in Roxbury Connecticut. 2 Bedrooms, Full Kitchen, Full Bathroom, Living Room, Oversized Deck, Outdoor Grill, and 3+ Acres of Land with Outdoor Seating. Close to...
    View all property information
    Location Information
    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property
    Owner log in