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New Preston Family & Kid Friendly Rentals

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    Don't let other travelers get your favorite New Preston area vacation rental. You're so close to securing your perfect getaway. Book today.
    12 Matching Rentals in the New Preston AreaView all 22 rentals
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    Rhubarb Hill, a Charming 1850's Farmhouse1 / 21
    (1)Excellent
    New Preston
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 15 miles of New Preston.
    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling, NY
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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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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    Wingdale, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all in this vacation home on private lake and nature preserve nestled in the foothills of the Berkshires. Perched on a peninsula on the shores of Lake Weil (viewable via Google map), this stunning 4-bedroom contemporary home offers exclusive use of your own 30-acre lake. Pack a...
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    Location Information
    Wingdale, New York 12594
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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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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    Amenities & Details
    • Washer
    • Internet Access
    • Secure Parking
    • Mountain Views
    • Balcony
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 7, 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...
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    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...
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    Location Information
    Southbury, Connecticut 06488
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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 August 30, 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
    Bethlehem, Connecticut 06751
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Sherman
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Grill
    • Housekeeping Included
    • Waterfront
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private secure community with million dollar homes. Perfect weekend retreat. 90 minutes from NYC. This two bedroom cottage has all the necessary amenities. Includes access to two private beaches on Candlewood Lake and Green Pond. Just renovated with new wood floors, new appliances, new...
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    Sherman, Connecticut 06784
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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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    Location Information
    Bethlehem, Connecticut 06795
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Architect-designed, contemporary, 3-bedroom country home. Sited on five private hillside acres with breathtaking views of the Housatonic River Valley in the foothills of the Berkshire Mountains. With geothermal heating and air conditioning, heated floors, wood, slate, and stone flooring, gourmet...
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    Location Information
    West Cornwall, Connecticut 06796
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    New Milford, Connecticut 06776
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Comfortable Rustic Cottage on 4 Wooded Acres with Brook1 / 22
    (3)Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2015
    Really enjoyed staying here with y sister and partner and my family (three young kids), who played endlessly in the stream which was full of frogs and stones. We could relax...
    Reviewed January 30, 2015
    This was a wonderful cabin, no bells or whistles, but all of the amenities. It was comfortable clean and very spacious. The floor plan lends itself to lots of nooks and crannies...
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    About this property
    Furnished cottage, with large deck, on 4 acres of woods, with brook and 200 feet Housatonic River frontage. Use of Sharon beach, tennis courts, and children's play area. The brook will dry up during summer dry spells. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from...
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    Location Information
    West Cornwall, Connecticut 06796
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Yard
    • 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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    Location Information
    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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