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.

Old Greenwich 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
    $390 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Old Greenwich area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 26 Rentals in Old Greenwich
    Sort by:
    Default
    The following rentals are within 25 kilometres of Old Greenwich.
    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
    Elegant, Newly Renovated 5 Bedroom Home1 / 25
    (3)Very good
    White Plains, NY
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    NYC Midtown 30 minutes-Scarsdale on Golf Course1 / 23
    (5)Excellent
    Scarsdale, NY
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Greenwich
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    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
    Glen Cove, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Internet Access
    • Parking
    • Air Conditioning
    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for an easy-going New York getaway, this 3-bedroom, 2.5-bath vacation rental house is a splendid home base in Glen Cove. This home sleeps up to 7 travelers, boasts 2 living spaces, a private heated pool, and hot tub. Enjoy a shopping spree at the Americana Manhasset Mall just 15 minutes away....
    View all property information
    Location Information
    Glen Cove, Long Island 11542
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    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
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/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
    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
    Quaint and immaculate 3 br duplex!1 / 26
    (1)Excellent
    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2017
    From opening the front door, we felt at home.It was so inviting, well equipped and we found out with in days that we need a Fridge Freezer with an ice dispenser/cold water in...
    See all reviews
    About this property
    Minutes from Byram beach and also from the main streets of Port Chester, Rye and Greenwich, this fully renovated home boasts hard wood floors, washer dryer, central heating and air conditioning and a wonderful state of the art kitchen with granite counter tops. The property has 3 quaint bedrooms...
    View all property information
    Location Information
    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Bedford, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in a comfortable home in Bedford, NY. You will feel right at home enjoying this house. It sits on 1.5 acres in an upscale neighborhood in one of the most prestigious and elegant New York suburbs. Incredible restaurants, hiking and NYC all within an easy drive. The space Nice big kitchen....
    View all property information
    Location Information
    Bedford, Westchester County 10506
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Save time - get the best Old Greenwich rentals sent straight to your email!
    Get the List
    Stamford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Country Cottage, Kitchen has a stove, microwave, Refig, Double Sink. Living Room, Bedroom, Stiral Staircase to bedrooms, Outside deck, Horses and dogs on property. 7 miles to train station, New York City. 5 Miles to Stamford night life. Walking trails, trout fishing.Very peaceful...
    View all property information
    Location Information
    Stamford, Connecticut 06903
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Bayville, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a luxury, modern, waterfront house with 4500 square ft. There are 10 large rooms. All rooms have wall to wall glass windows overlooking the bay. Brand new house with all brand new appliances. KItchen, 2 living areas, 2 fire place 2, dining room, family room, recording studio, meditation...
    View all property information
    Location Information
    Bayville, Long Island 11709
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Cable/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
    New Rochelle, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private beach house. Hidden vacation gem, a fully furnished, spacious, affordable home on a quiet street, only steps from your front porch to a private beach on Long Island Sound. Convenient--it's only a half hour by train or car from Grand Central Station. Great for walking, biking, swimming,...
    View all property information
    Location Information
    New Rochelle, Westchester County 10805
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    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
    • Cable/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
    White Plains, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely Victorian in White Plains AVAILABLE FOR JULY +- a week or so We are on a hill, facing WEST so we get some fantastic sunsets. Close to Manhattan, White Plains is a small city, and a unique suburban community. This wonderful Victorian style house was built in 1902. We have lived here for 35...
    View all property information
    Location Information
    White Plains, Westchester County 10606
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    Home1 / 14
    (1)Average
    Pelham, NY
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2016
    Location was perfect for our purpose. Close to village shops and cafes. Rooms and beds are decent and comfortable enough.Friendly owner. We have suggestions for improvement...
    See all reviews
    About this property
    In the peaceful Village of Pelham, at few blocks from Metro North Train Station there is a large home, with a barbeque area. To rent only : 2 bedrooms with separate entrance and 1 bathroom. With the Metro North you are in New York Grand Cental in 30 minuets. Walking distance from restaurants, park...
    View all property information
    Location Information
    Pelham, Westchester County 10803
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Make Enquiry
    Chappaqua, NY
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Parking
    • Balcony
    • Air Conditioning
    • Internet Access
    • Shared Garden
    • Outdoor Dining Area
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottage at Stone Croft is a quick train ride to Manhattan, but looks out on woods and a stream. The cottage is like a two story suite with a full kitchen. There is a queen bed in the main bedroom and a queen sofa bed upstairs. A great place for families and kids. There is a dishwasher,...
    View all property information
    Location Information
    Chappaqua, Westchester County 10514
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    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
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Rye, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is good for couples or families with kids. Colonial English Cottage property built in 1925. The house is in a great location close to all the Rye amenities and only 23 minutes to NYC by train. There are a two car garage and plenty of parking in the driveway. You will be 5 walking distance...
    View all property information
    Location Information
    Rye, Westchester County 10580
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Enquiry
    Mount Kisco, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated at the end of a quiet, semi-private road, this delightful Country Retreat offers a tranquil and serene experience for your vacation stay. The lush trees will embrace you and provide a sense of seclusion, yet the wide-open space allows for wandering eyes to breathe in the stunning views of...
    View all property information
    Location Information
    Mount Kisco, Westchester County 10549
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Pelham, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelham Train Station 1 Bed 1 Bath - A This 1 Bedroom 1 Bathroom has two flat screen TV's with Directv including NBA and NFL packages. There is high speed internet Just a 2 minute walk to the train which is just 28 minutes to NYC's Grand Central Station. The apartment features bleached hard wood...
    View all property information
    Location Information
    Pelham, Westchester County 10803
    Condo/Apartment - 1 Bedroom, 1 Bathroom, 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
    • Cable/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
    Bronxville, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly set amongst majestic century old trees and mansions in the Historic Cedar Knolls Colony (Once home to Charlie Chaplin) and on the grounds of the Jerome Kern Estate. Pricing Excludes Holiday week. Short Walk to Bronxville (Metro North) Train Station. A perfect floor plan for everyday as...
    View all property information
    Location Information
    Bronxville, Westchester County 10708
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    White Plains, NY
    5 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • DVD Player
    • Patio
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Its an older home built in 1906 and bought by my grandparents 50 years ago. It has a landscaped front and back yard that is professionally maintained. There is a large driveway that can hold an ADDITIONAL 5+ vehicles. There is a back patio where you can grille and lounge. There is a table and...
    View all property information
    Location Information
    White Plains, Westchester County 10606
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property
    Owner log in