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Waterbury Vacation Rentals

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    Don't let other travelers get your favorite Waterbury area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 28 Rentals in Waterbury
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    The following rentals are within 15 miles of Waterbury.
    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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    Newly remodeled 1891 Queen Anne Victorian mansion1 / 10
    (1)Excellent
    Wallingford
    1 Bedroom, 2 Bathrooms, Sleeps 2 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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    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 14, 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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    Hamden, Connecticut 06514
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bethlehem
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • 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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    Bethlehem, Connecticut 06795
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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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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    Southbury, Connecticut 06488
    Rental Home - 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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    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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    Bethlehem, Connecticut 06751
    Private Room - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    North Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Central Heating
    • Parking
    • Private Yard
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled home with 3 bedrooms, 1.5 baths, family room, finished basement that can easily accommodate 8 people and is near everything. Just a quick commute to Yale, SCSU, Quinnipiac and the University of New Haven, very close to the best restaurants in the greater New Haven area and within...
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    North Haven, Connecticut 06473
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Meriden
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 level Townhouse located in the Prestigious area of Mattabassett in Meriden. Enjoy beautiful Mountain View’s. Maintance free grounds, walking paths, ponds, pik nik tables, swings, baseball area, community pool (summertime) and so much more. Conveniently located to major highways,...
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    Meriden, Connecticut 06450
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 Yard
    • 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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    Hamden, Connecticut 06514
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Seymour
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • 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
    Seymour, Connecticut 06483
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Litchfield House on Half Acre - 1 Mile to Town!1 / 25
    (1)Excellent
    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • 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 November 13, 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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    Litchfield, Connecticut 06750
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    North Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Terrace
    • Wi-Fi
    • Parking
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely house in North Haven, CT has been recently remodeled. It is centrally located and just minutes from Yale, Quinnipiac, UNH, SCSU and Albertus as well as shopping, the best restaurants, hiking trails in West Haven, Hamden and Wallingford, state parks and many local attractions including...
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    Location Information
    North Haven, Connecticut 06473
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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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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    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Harwinton
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Weekly rental April through December, monthly rental offered January thu March. 2 bedroom, 1 bath, fireplace, with beautiful views of the lake Enjoy a classic New England vacation in this direct lake front home on Harwinton Lake. Relax and enjoy the pretty scenery and breezes in this quiet lake...
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    Harwinton, Connecticut 06791
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southbury
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Yard
    • 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
    Southbury, Connecticut 06488
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Farmington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and unwind by the water when you stay at this 3-bedroom, 2-bathroom vacation rental house in Farmington. Situated in a quiet community, this home boasts accommodations for up to 6 guests and 2,200 square feet of living space. Spend your days exploring the area, visiting museums, or take a day...
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    Farmington, Connecticut 06032
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    Roxbury, Connecticut 06783
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Washington Depot, Washington 06794
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Washington Depot
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    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
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    Washington Depot
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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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
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    Washington Depot
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
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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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    Washington Depot, Washington 06794
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    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
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    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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    Washington Depot, Washington 06794
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Washington Depot
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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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, 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
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    Washington Depot
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
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