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.

Holiday Rentals in New Canaan

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
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
    Price
    per night
    €283 Average
    |||
    |||
    €0€1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite New Canaan area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in New Canaan
    Sort by:
    Default
    The following rentals are within 25 kilometers of New Canaan.
    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Charming and immaculate 3 br duplex!1 / 17
    (7)Excellent
    Greenwich
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    South Salem, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Washer
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Its a great house on half an acre. Starting at 199 Per night. All updated. Much better than three pictures.Brand new kitchen appliances. restaurant begin two houses away. Walk to everything. Yes really one minute to stores restaurants markets and lots of stores etc. Shuttle stops at our door to...
    View all property information
    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 21
    (2)Very good
    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Patio
    • Washer
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2015
    The apartment was in a lovely setting, attached to the family house, but totally private. Liz the landlord was very friendly, helpful and knowledgeable of the area. The...
    See all reviews
    About this property
    Completely updated apartment in lovely rural setting but close to everything. Get away without going very far. Take a break from sterile hotel rooms while on business. Private entrance, 2 bedroom, 1.5 bath, fully equipped kitchen, dining room, living room, french doors to patio, balcony off...
    View all property information
    Location Information
    Stamford, Connecticut 06903
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Weston
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    • Air Conditioning
    • Internet Access
    • Balcony
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Master Bedroom with four additional bedrooms -- two are double height with lofts. The home features 18" soaring ceilings, an incredible wrap around deck overlooking lawns and gardens. Large Italian eat-in kitchen/family room. Office for 4. Home theater. Whole-house B&O system. Badminton, ping pong,...
    View all property information
    Location Information
    Weston, Connecticut 06883
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Greenwich
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 4 bedroom home at the end of a quiet country lane on a horse farm. Country kitchen with a lovely patio and grill. Heated and cooled with recently installed geothermal enjoy peace and tranquility in a beautiful setting. Horses live on the property, please inquire about lessons or trail...
    View all property information
    Location Information
    Greenwich, Connecticut 06831
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    Make Enquiry
    Private pool house with access to pool and tennis1 / 6
    (1)Excellent
    Darien
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2016
    I stayed lots of place before but David and his family was awesome ! We had a lot of fun in their pool house, tennis and basketball court and mini soccer area.Every single...
    See all reviews
    About this property
    This is a private pool house with queen bed and kitchenette on a 3 acre property. There is a pool steps away as well as a tennis court on the property and you will have full access to both. There is a bathroom with shower and other amenities can be provided. We are close drive to the beach in town....
    View all property information
    Location Information
    Darien, Connecticut 06820
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Southport
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Grill
    • Ocean Views
    • Air Conditioning
    • Balcony
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new private one bedroom apartment on estate with full kitchen, marble bathroom and open living room with beautiful views and outdoor shower. Located on the "Gold Coast" between Westport and Fairfield. A great getaway stocked with beach equipment, bikes and outdoor grill, quality sheets and...
    View all property information
    Location Information
    Southport, Connecticut 06890
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Greenwich
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Private Garden
    • Secure Parking
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Greenwich, Connecticut 06831
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Greenwich
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With my children off to college I have an empty 3rd floor (so availability is around the school calendar). Neat 3rd floor unit with its own bedroom, separate sitting room, small fridge, microwave, coffee-maker, bathroom (stall shower), TV, and table for 4. Ideal for someone working weekdays in...
    View all property information
    Location Information
    Greenwich, Connecticut 06830
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Fairfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Balcony
    • Grill
    • Patio
    • Washer
    • Terrace
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This new contemporary beach house has an open floor plan on the first floor with an 8' granite island that seats 4. Fireplace has a 60" Smart TV that hangs from it. Beautiful dining area seats 10. Outdoor gas grill easily facilitates eating al fresco. Each floor has an outdoor furnished deck. Each...
    View all property information
    Location Information
    Fairfield, Connecticut 06824
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Black Rock~ Fairfield County's hidden gem!1 / 14
    (1)Excellent
    Bridgeport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Waterfront
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2014
    This property is located in a quiet residential location, directly behind one of many small yacht clubs in this area. We found it spacious enough for our family of 2 adults and...
    See all reviews
    About this property
    Enjoy spectacular sunrises and sailing regattas while sipping coffee from the back decks of this charming townhome. Black Rock is a historical peninsula within walking distance to trendy restaurants, tranquil beaches, and Metro North train station with just over an hour ride to New Yok City. Ride...
    View all property information
    Location Information
    Bridgeport, Connecticut 06605
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Easton
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our large and luxurious home is open to you for your enjoyment and relaxation. With 4 en-suite bedrooms and 2 additional bedrooms, the house is able to comfortably accommodate large groups of people for short stays. The house is in immaculate condition and boasts luxury appointments and and...
    View all property information
    Location Information
    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
    Make Enquiry
    Weston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy cottage sits on a family property in a small neighborhood (faces the main house on a circle driveway). It has been renovated with all new appliances and new floors while still maintaining it's cozy retreat feel. Each bedroom features a queen size bed. There is also a screened in porch for...
    View all property information
    Location Information
    Weston, Connecticut 06883
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LOCATION, LOCATION, LOCATION... MY HOME IS CENTRALLY LOCATED, SO EVERYTHING YOU NEED AND WANT IS EASILY ACCESSIBLE. IT'S CLOSE TO THREE BEACHES, DOWNTOWN SHOPPING, RESTAURANTS, HISTORIC WESTPORT COUNTRY PLAYHOUSE, AND RAILROAD STATION! IT'S ALL JUST MINUTES AWAY BY CAR, AND NOT ALL THAT FAR TO...
    View all property information
    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Greenwich
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Greenwich, Connecticut 06831
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Greenwich
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Balcony
    • Terrace
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and elegant three bedroom, two and one half bath, 1,900 SF condominium built in 2003. The first floor offers a large living room with two exposures, a gourmet eat-in kitchen with sliding doors that access an outdoor sitting area and garden. The generous master bedroom with en-suite bath is...
    View all property information
    Location Information
    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Westport
    3 Bedrooms, 9 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Terrace
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This direct waterfront getaway boasts an open floor plan with spectacular full water views throughout. Experience glorious energizing sunrises and exquisite sunsets to begin and end your magical days in this tranquil setting. Custom modern European inspired gourmet kitchen with top of the line...
    View all property information
    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 9 Bathrooms, Sleeps 7
    Make Enquiry
    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Patio
    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located directly on Long Island Sound in the residential section of Saugatuck Shores, this recently renovated, completely furnished, 3 bedroom, 2 bathroom house offers wide unobstructed views of the water from the front porch and the second floor deck. It has new stainless kitchen appliances, new...
    View all property information
    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Pound Ridge, NY
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A luxury cottage set privately on a 7 acre estate in sylvan Pound Ridge, New York. A perfect setting from which to explore Westchester's horse country, The Hudson Valley, New England's Connecticut villages and New York City. World renowned restaurants are within minutes and recreational activities...
    View all property information
    Location Information
    Pound Ridge, Westchester County 10576
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Westport
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Terrace
    • Outdoor Dining Area
    • Satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Elegant home was professionally designed to capture the spectacular views of the Ocean. The home was completely remodeled recently and includes a rich interior with state of the art kitchen appliances, wood burning fireplace, washer/dryer, central A/C and internet. Near the end of a quiet...
    View all property information
    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Satellite TV
    • Parking
    • Grill
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lauren Berger Collection is proud to be recognized as one of the best Vacation Rental companies in the world by the best, The Vacation Rental Guide. A forty-five minute drive from Manhattan but a world away from the clamor, this serene, elegant home is set on an acre of rolling lawns in one...
    View all property information
    Location Information
    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    North Salem, NY
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Grill
    • Balcony
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gracious and well appointed Coach House has been beautifully renovated. The Light and Airy Two Floor cottage is situated on the property of an historic home, and offers a Pool, mature gardens, riding and hiking trails. It's near excellent fishing spots. Dine al fresco on your private patio!...
    View all property information
    Location Information
    North Salem, Westchester County 10560
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    Make Enquiry
    Westport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1898, exposed unfinished beams and pillars, Charming low ceilings and a couple of original doors, make it a residence with genuine soul and character. Upstairs is a semi open space, no doors or full walls-half walls separate sleeping spaces. Has a queen bed and a traditional Japanese...
    View all property information
    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Stamford
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Housekeeping Included
    • Balcony
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In this high-ceiling sunny downtown loft, there is a family atmosphere and eclectic furniture and decor. It is close to local activities (parades, fun-raisers, fun runs...etc), great nightlife, public transport: the bus is across the street, the city center (only a 1/4 mile away), restaurants,...
    View all property information
    Location Information
    Stamford, Connecticut 06905
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Make Enquiry
    Easton
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Jan 02 : Tuesday, Thursday, Wednesday, Friday, Monday, Saturday and Sunday check-in required, Tuesday, Thursday, Wednesday, Friday, Monday, Saturday and Sunday check-out required.; Our large and luxurious home is open to you...
    View all property information
    Location Information
    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    List your property
    Owner log in