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Roxbury Vacation Rentals

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    Don't let other travelers get your favorite Roxbury area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 24 Rentals in Roxbury
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    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 15 miles of Roxbury.
    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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    Quiet Getaway in Historic Village1 / 27
    (1)Excellent
    Southbury
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 24, 2017
    This review is long overdue. My mom and I stayed at this extraordinary home for close to a month and it couldn’t have been more perfect! The grounds were beautiful, a...
    Reviewed June 21, 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...
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    About this property
    My home has all the amenities for a perfect family/friends getaway. The chef's kitchen is fully equipped and totally at your disposal. Three good grocery stores and the 4.5 star New Morning Market and Health Food Store are nearby for your food shopping convenience. Most guests, however, prefer...
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    Location Information
    Woodbury, Connecticut 06798
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    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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    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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    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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    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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    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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    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling, NY
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Private Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2017
    Love the place. It was great for our family. Very spacious and clean. The place is also located in a great area so it was perfect. We will rent it again next year for our...
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    About this property
    You will have full access to this 2 bedroom camper that sleeps 8. We are located on a private/quiet road. This is not a camp ground. You will be the only family staying with us. We have a huge in ground salt water system pool that you will have full access to. We live here on the grounds, so the...
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    Location Information
    Pawling, New York 12564
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • Private Yard
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This former servant's quarters w/full bed has private bath with claw foot tub/shower. Original back staircase just outside the door which leads directly to the kitchen. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten people staying...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Location Information
    Sherman, Connecticut 06784
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated room with private bath, queen bed, antique furniture and Cable TV. Shared living room, dining room, porch, and kitchen. On Main Street in town. Plenty of parking. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Room with private bath, queen bed, antique furniture, air conditioning, and radiator heat. Shared living room, dining room, porch, and kitchen. On Main Street in town. Plenty of parking. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 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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    Location Information
    Litchfield, Connecticut 06750
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Grill
    • Air Conditioning
    • Private Yard
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large master suite with private bath including claw foot tub and stall shower. Queen bed with sitting room area, window air conditioner. Shared living room, dining room, porch and kitchen. On Main Street in town. Please enjoy all the common areas in the home. We do not live in the home and there...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Private Yard
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    First floor suite king bed, couch and desk. Sitting room with single bed, chairs, television and desk. Large bath with stall shower. Shared living room, dining room, porch and kitchen. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 3
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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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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 7, 2014
    We arrived all type A with many plans to hike and swim, ended up enjoying the comfort of the house, cooking, hanging out together. Switching from indoor seating for outdoor...
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    About this property
    Near Lake Waramaug $300 per night with a 3-night minimum $1800 per week. June $6,000 per month July $6,000 per month Aug $6,000 per month Memorial Day to Labor Day $14,000. During the winter months-mid-October-mid-March, I seek long term rentals. I only rent by the month during this...
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    Location Information
    New Preston, Connecticut 06777
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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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    New Milford, Connecticut 06776
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Warren
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Parking
    • Washer
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Note that this home can be rented in conjunction with VRBO listing 3921932ha (Evolve #256841) for discounted rates. Please inquire for additional info ** Seeking the perfect place to stay for your next peaceful getaway? Look no further than ‘Carriage House!’ Situated on the Lake Waramaug...
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    Location Information
    Warren, Connecticut 06777
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    New Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor a piece of Connecticut paradise at this 3-bedroom, 2-bathroom New Fairfield vacation rental house! Suitable for up to 10 guests, this Hampton-style home featuring an outdoor kitchen and 4 levels of outdoor space provides travelers with an ideal location on Candlewood Isle, where you can enjoy...
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    Location Information
    New Fairfield, Connecticut 06812
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    New Preston
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Central Heating
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit the beautiful shores of Lake Waramaug in this charming 3-bedroom, 2-bathroom New Preston vacation rental cottage that comfortably sleeps 6. Relax and recharge on the brand new stone patio and spend your days by the water on the private lakefront area and 22 foot dock. With 1,300 square feet...
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    Location Information
    New Preston, Connecticut 06777
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newtown
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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
    Newtown, Connecticut 06470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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