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Roxbury Holiday Homes

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    Don't let other travellers get your favourite Roxbury area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Roxbury
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    Roxbury
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 25 kilometres of Roxbury.
    NEW! 3BR Litchfield House on Half Acre of Land!1 / 24
    (1)Excellent
    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 7 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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    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2014
    This is a spacious 4 bedroom property. it is high above the local road and is surrounded by trees. Neighbours are a good distance away, so the loudest sounds are from the local...
    Reviewed 22 July 2014
    A spectacular week in a secluded spot and yet minutes from quaint New Milford Village. Pool is GREAT
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    About this property
    LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful!! very private country setting; four bedrooms, large family room with cathedral ceilings and grand piano. All amenities: cable TV, CD, DVD,VCR, internet and air conditioning. Deck--including a screen house; gas grill. 20x40 inground pool with...
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    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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 8 January 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    New Milford
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1840 completely renovated country house with lots of room, convenience and quietness. 4,000 sq. ft. furnished with many antiques. A most unique country kitchen, formal dining room, eat-in kitchen, library, living room, den, five bedrooms (some have 'Sleep Number' mattresses), and 5 and a half...
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    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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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 8 July 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Its the Perfect Weekend House just 80min from NYC!1 / 23
    (4)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 2 weeks ago
    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 22 June 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
    This Perfect Weekend House, a quick getaway from NYC, is all yours. It is four comfortable bedrooms on the peaceful edge of time. Antiques, artworks, photographs, and sculptures fill this light-splashed two story 2.5 bath home on Connecticut's Antique Trail. These spacious indoor and outdoor...
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    Location Information
    Woodbury, Connecticut 06798
    Holiday Rental House - 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
    • Housekeeping Included
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is in a historic village with 22 others clustered around the Congregational Church across the street from the house. Built in 1795 it has four large corner rooms on both floors On the first floor there's a central entry hall, with dining and library to either side, straight ahead are...
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    Location Information
    Southbury, Connecticut 06488
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Washington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Street is a mint condition 4 bedroom home with a heated pool, wonderful flat private quiet yard with a swing set far back from the street. The home is in Washington, the most desirable historic rural town in Litchfield County with wonderful restaurants, land preserves, private schools,...
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    Location Information
    Washington, Connecticut 06793
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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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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    Location Information
    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 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
    Bethlehem, Connecticut 06751
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling, NY
    2 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 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 12. 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 12
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    Danbury
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exceptional Waterfront Vacation Home! Located on Connecticut's largest man-made lake, Lake Candlewood. A perfect location for those day trips into NYC either by car or train! Picturesque perennial gardens, stunning lake views & an enticing lakefront w/sand beach, dock & more! A Gracious foyer...
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    Location Information
    Danbury, Connecticut 06811
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    New Preston
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Central Heating
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Warren
    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Patio
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that this property can be rented alongside with VRBO listing 3921932ha (Evolve #256841) for discounted rates. Please inquire for additional information** When searching for the perfect place to stay for your next peaceful family gathering, 'Carriage House' is just the spot for you....
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    Location Information
    Warren, Connecticut 06777
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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