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.

Southbury Vacation Rentals

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
    C$720 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Southbury area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Southbury
    Sort by:
    Default
    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
    Southbury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Southbury
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 25 kilometres of Southbury.
    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 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...
    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
    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 August 10, 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 July 21, 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
    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
    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 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...
    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 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...
    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
    Seymour
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Seymour, Connecticut 06483
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    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 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...
    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 Southbury rentals sent straight to your email!
    Get the List
    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
    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • 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...
    View all property information
    Location Information
    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    New Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    New Fairfield, Connecticut 06812
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Newtown
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Newtown, Connecticut 06470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    New Preston
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Roxbury
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Roxbury, Connecticut 06783
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    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,...
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    Washington Depot
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Washington Depot
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Washington Depot
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    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....
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    Washington Depot
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Private Garden
    • 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...
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    Washington Depot
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Washington Depot
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Make Enquiry
    Washington Depot
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Washington Depot, Washington 06794
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    List your property
    Owner log in