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Holiday Homes in Middlebury

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    Don't let other travellers get your favourite Middlebury area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Middlebury
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    The following rentals are within 25 kilometres of Middlebury.
    Its the Perfect Weekend House just 80min from NYC!1 / 19
    (5)Excellent
    Woodbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Quiet Getaway in Historic Village1 / 27
    (1)Excellent
    Southbury
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    20'x40' inground private pool just for you&house with 4bedrooms1 / 36
    (4)Excellent
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Private 2 bedroom near Yale, downtown, great restaurants and parks1 / 9
    (1)Excellent
    Hamden
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2018
    Thank you to Geraldine for the opportunity to spend time in this good feeling, homey, rental space.We enjoyed the space, the gracious hospitality of our hosts, and the time they...
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    About this property
    Beautiful, clean, quiet, private 2 bedroom apartment on bus line. Minutes from Yale, downtown, parks, restaurants (best pizza in the world!!!) includes new stove, oven, large fridge. Plates, coffee machine, linens, tv, just bring fire stick or whatever you prefer to hook up to our free WiFi. No...
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    Location Information
    06514, Hamden, Connecticut
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southbury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    • Wi-Fi
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There are two ways of renting: THE HOUSE RENTAL which can be for short terms or up to six months. The house is the largest and most spacious of the homes remaining in the historic Village of South Britain. It was built in 1795 at the zenith of its industrial factories producing as much or more...
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    Location Information
    06488, Southbury, Connecticut
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Wits End Farm B&B1 / 14
    (1)Excellent
    Bethlehem
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Our family stayed at Wits End Farm B&B for a weekend in early June for our son's graduation from a local boarding school. We can't say enough about our time there. Our host...
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    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...
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    06751, Bethlehem, Connecticut
    Private Room - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Bethlehem
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    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...
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    06795, Bethlehem, Connecticut
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    Wits End Farm1 / 16
    (1)Excellent
    Bethlehem
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Our family stayed at Wits End Farm B&B for a weekend in early June for our son's graduation from a local boarding school. We can't say enough about our time there. Our host...
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    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...
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    Location Information
    06751, Bethlehem, Connecticut
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Litchfield House on Half Acre - 1 Mile to Town!1 / 24
    (1)Excellent
    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2017
    Litchfield is a charming small town that is a popular weekend destination for New Yorkers. It has a few good restaurants and boutique shopping, plus the interesting historical...
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    About this property
    Relish in the luxuries and comforts of this 3-bedroom, 2-bath vacation rental house in Litchfield! 'Stone-Peca' is a quintessential New England property sitting on a half acre of land, offering a 4-season sun porch as well as a spacious backyard with a deck and patio. Stylish, high-end decor adorns...
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    Location Information
    06750, Litchfield, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Hamden
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Patio
    • Grill
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Royal Master Suite offers the finest set of amenities similar to those found in any luxury resort. With plenty of room to live, breathe, read, or sleep in comfort, this boudoir is truly a treat. This Colonial Home has a warm, inviting atmosphere with a hostess who is knowledgeable about...
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    Location Information
    06514, Hamden, Connecticut
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house has a soul. It is not like a fancy hotel but instead all elements of decor have some story to tell. The indoor is painted by an artist. We have grand piano which if you know how to play will make time together more fun. The pool is just amazing. Deep end has 8' and shallow 4.5'.We love it...
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    Location Information
    06776, New Milford, Connecticut
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Seymour
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our apartment is very comfortable for either short-term or long-term stay. We have everything you may need. This fully furnished ground floor apartment features a spacious living room and separate bedroom with a comfortable queen size bed; Daybed with Trundle Set, Twin Size; two futons; additional...
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    Location Information
    06483, Seymour, Connecticut
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • Cable/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...
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    06783, Roxbury, Connecticut
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southbury
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be staying in a house that was built in 1795. It is as it was built, except for the modern kitchen and baths. You'll share the house with the Architect Owner and a possible guest in The Artist's Studio and Bed Room unless your party takes both bedrooms. Enjoy the living and dining rooms...
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    Location Information
    06488, Southbury, Connecticut
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Newtown
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the homeowner lives onsite, in the separate unit, and may be present during your stay ** Have a comfortable stay with your closest friends at this 1-bedroom, 1-bath apartment in Newtown. Nestled on the second floor of a fully restored 1890 vintage Victorian home, this unit...
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    Location Information
    06470, Newtown, Connecticut
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Roxbury
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meticulously restored country house on scenic dirt road in historic Roxbury near Washington town line. Barn, small pond, stream on a great flat dirt road perfect for walking, jogging, biking. 5 minutes to the Mayflower Inn & Spa and Washington Center and Steeprock Preserve. Close to Lake...
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    Location Information
    06783, Roxbury, Connecticut
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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