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Woodbury Vacation Rentals

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    Its the Perfect Weekend House just 80min from NYC!1 / 32
    (6)Excellent
    Woodbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Woodbury
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Cosy Guest Cottage in Gated Residence1 / 22
    (3)Very good
    Woodbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 10 miles of Woodbury.
    Oakville
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    IMPRESSIVE VILLA WITH PRIVATE POOL: Impressive villa with private pool with capacity for 10 people. ​It consists of 3 bedrooms with double beds (one en suite with shower and bathtub), 2 bedrooms with double sofa bed, 3 bathrooms, fully equipped kitchen (with garbage disposal), covered garage, air...
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    Oakville, Connecticut 17250
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Country Estate newly renovated that sleeps 16!1 / 31
    (1)Excellent
    Bethlehem
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Parking
    • Grill
    • Housekeeping Included
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 31, 2019
    Walking into this home was like walking into my parents home. The home is the epitome of a "turn key" home.; it had everything we needed to be comfortable. I highly...
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    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 that are tastefully decorated....
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    Bethlehem, Connecticut 06795
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 16
    Oakville
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Cable/satellite TV
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful modern apartment, fully equipped.: ​Very comfortable, living room with access to balcony, with outdoor furniture and views of the city.Fully equipped dining room, large sofa chess lounge, last generation TV, with foreign channels, folding to watch from living room, dining room or...
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    Oakville, Connecticut 17250
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Southbury
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • 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
    Southbury, Connecticut 06488
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Wits End Farm B&B1 / 14
    (1)Excellent
    Bethlehem
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
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    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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    Bethlehem, Connecticut 06751
    Private Room - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Wits End Farm1 / 16
    (1)Excellent
    Bethlehem
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • 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
    Oakville
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Grill
    • Balcony
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CHARMING FISHERMAN HOUSE WITH TERRACE: Beautiful fishermen's house with a big terrace, recently rehabilitated and renovated but preserving some ancient details. Located 300 meters from the beach and the walls of Vila Vella de Tossa de Mar. DISTRIBUTION: House with 3 floors, equipped with Wi-Fi and...
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    Location Information
    Oakville, Connecticut 17320
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Britain
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
      This beautifully antique-furnished home opens onto and has access to two acres of open grounds. Located in the heart of the the Village of South Britain founded in 1709 it's within walking distance of 22 historic homes, a Congregational and Methodist Churches built in the 1830's, an 1889 town...
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    Location Information
    South Britain, Connecticut 06488
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Oakville
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Ocean Views
    • Wi-Fi
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Apartment directly to the sea.: On the beach of Pals, directly to the beach, apartment in building Villa del Golf. Building with comunal pool, garden and table tennis. Ground floor and 3 storey bulding. Apartement located at the 3. floor. Elevator. The apartment consist in a kitchen, sitting-dining...
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    Location Information
    Oakville, Connecticut 17256
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Washington Depot
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    About this property
    Sunny Ridge Farm is a magnificent country estate on 14 acres in the Sunny Ridge Historic District. It is the largest home (17,000 SF) in Washington, the most exclusive town in rural Litchfield County. The estate has been meticulously restored and has almost every possible amenity - 8 over sized...
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    Location Information
    Washington Depot, Washington 06794
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 16
    Oakville
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    QUIET APARTMENT IN TOSSA 4: Apartment located in a quiet area at the same time as close to everything. DISTRIBUTION: The apartment has 1 bedroom, a bathroom, living room with open kitchen and terrace. Capacity to sleep 4 people with the following distribution: - Room with two single beds. -...
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    Location Information
    Oakville, Connecticut 17320
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Washington Depot
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    Luxury exceptional design 4 Bedroom home in the best Roxbury location with firepaces and heated pool. Fully restored with a luxury kitchen, great room porch, den with a sleeper sofa, 4 bedrooms, 4 full bathrooms. Frette sheets, bathrobes, linens, down feather beds, comforters and pillows. Flat...
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    Washington Depot, Washington 06794
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Washington Depot
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very Large 4300 SF Single-Family 5-Bedroom home with heated pool, large eat-in kitchen plus second kitchen, high ceilings, 2 fireplaces, best Roxbury quiet (no parties, events, multi-person shares) estate neighborhood surrounded by land preserves overlooking a pond and across from a hundred-acre...
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    Location Information
    Washington Depot, Washington 06794
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Washington Depot
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Private Mint 5-Bedroom, 4-Bath Country Estate in one of Washington's Best neighborhoods surrounded by large estates. Heated pool, trampoline, game room, gas bbq, 2 gas fireplaces. A short drive to the Mayflower Inn & Spa and other Washington Restaurants, Galleries, Shops and Litchfield Shopping and...
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    Washington Depot, Washington 06794
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    If you are searching for the perfect country escape, Shaker Modern is for you! Set on 11 groomed hill-top acres, this meticulously restored home overlooks and abuts the Steep Rock Land Preserve on the Washington/Roxbury border. This light and airy mint home has 6 bedrooms and 4.5 marble bathrooms,...
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    Washington Depot, Washington 06794
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Perfect 6BR 3.5 Bath 4 Fire-Place home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT....
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    Washington Depot, Washington 06794
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Washington Depot
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    If you are searching for the perfect country setting within an easy drive to wonderful local restaurants, spas, shopping, antiquing, skiing, water activities, hiking, historic homes and museums, then Country Cottage is for you. Wonderful family activities such as apple picking, farm stands, country...
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    Washington Depot, Washington 06794
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Washington Depot
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Located in the heart of Washington in the best location, this renovated cottage is perched on 25-acres offering total privacy and spectacular 270-degree views. The home has a perfect entertaining terrace wit a gas barbecue and a heated infinity waterfall pool. The first story has 3 bedrooms, a...
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    Washington Depot, Washington 06794
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Watertown
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Yard
    • Wi-Fi
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pet friendly in town 2 bedroom house that sleeps 6. Fenced in wooded backyard & flower garden. Kitchen appliances large & small updated 2016- granite countertops. Stocked kitchen with spices & basics. Spacious bedrooms with queen size beds, TV & full size closets. Full bath, towels, soap &...
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    Watertown, Connecticut 06795
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Washington Depot
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Located in the best historic walking/biking/running neighborhood in Washington! Pristine barn-style home, 5 bedrooms, 4 wood-burning fireplaces, pool, giant terrace with gas bbq set in an apple orchard with a heated pool. The gourmet kitchen is fully equipped with a Viking 6-burner gas range and...
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    Washington Depot, Washington 06794
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Southbury
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Yard
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    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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    Southbury, Connecticut 06488
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Mountain Views
    • Air Conditioning
    • Grill
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    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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    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Roxbury
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • 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
    Roxbury, Connecticut 06783
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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