We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Roxbury Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    AU$368 Average
    |||
    |||
    AU$0AU$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Roxbury area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in Roxbury
    Sort by:
    Default
    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 25 kilometres of Roxbury.
    New Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling, NY
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    20'x40' inground private pool just for you&house with 4bedrooms1 / 36
    (4)Excellent
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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
    See all reviews
    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...
    View all property information
    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Its the Perfect Weekend House just 80min from NYC!1 / 19
    (5)Excellent
    Woodbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 November 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 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...
    See all reviews
    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...
    View all property information
    Location Information
    Woodbury, Connecticut 06798
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Quiet Getaway in Historic Village1 / 27
    (1)Excellent
    Southbury
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Southbury, Connecticut 06488
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Southbury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Southbury, Connecticut 06488
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Wits End Farm B&B1 / 14
    (1)Excellent
    Bethlehem
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Bethlehem, Connecticut 06751
    Private Room - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Wits End Farm1 / 16
    (1)Excellent
    Bethlehem
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Bethlehem, Connecticut 06751
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    Rhubarb Hill, a Charming 1850's Farmhouse1 / 21
    (1)Excellent
    New Preston
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Save time - get the best Roxbury rentals sent straight to your email!
    Get the List
    Wingdale, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Wingdale, New York 12594
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
    Make Enquiry
    Bethlehem
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Bethlehem, Connecticut 06795
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
    Make Enquiry
    Sherman
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Sherman, Connecticut 06784
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Kent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Private Garden
    • 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...
    View all property information
    Location Information
    Kent, Connecticut 06757
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Make Enquiry
    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    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...
    View all property information
    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    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...
    View all property information
    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • Private Garden
    • 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...
    View all property information
    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Grill
    • Air Conditioning
    • Private Garden
    • 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...
    View all property information
    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Southbury
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • 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...
    View all property information
    Location Information
    Southbury, Connecticut 06488
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    List your property
    Owner log in