Holiday Rentals in Greenwich, CT

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Greenwich, CT holiday rentals
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Best Holiday rentals and Airbnb offers in Greenwich, CT

Best family friendly Greenwich, CT holiday rentals

Among the 226 accommodations in Greenwich, CT, here are the 4 best family friendly rentals

New Beach Home Near Stamford Downtown/shippan - Greenwich, CT
10 24 reviews
Greenwich, CT
10/09 – 19/09
SG$1790/nighttotal: SG$16110 (9 )

New Beach Home Near Stamford Downtown/shippan

5 9
apartment , Stamford
This spacious five-bedroom apartment is located in the desirable Shippan Point neighbourhood, just a short walk from West and Cummings Beaches and a few minutes' drive from parks, restaurants, and shops. It has received excellent user ratings and is a perfect choice for families and groups.
This comfortable home offers 260 square metres of living space and can accommodate up to 16 guests. The apartment boasts a fully equipped kitchen, a private garden with two large decks, and a range of entertainment options, including a billiards table, ping pong, and foosball.
Peaceful Lakeside Retreat In Greenwich [2br, 1ba] - Greenwich, CT
Greenwich, CT
30/08 – 30/09
SG$456/nighttotal: SG$14136 (31 )

Peaceful Lakeside Retreat In Greenwich [2br, 1ba]

2 1
apartment , Greenwich
This two-bedroom flat in Greenwich offers peaceful lakeside views of Frye Lake and convenient access to NYC train stations, located approximately 1.5 kilometres from the upscale shops and dining on Greenwich Avenue.
This family-friendly apartment accommodates up to four guests and features a garden area with a picnic table, air conditioning, WiFi, and parking.
Peaceful Pound Ridge Summer Retreat W/ Pool & 5 Bedrooms, 65 Min To Nyc - Greenwich, CT
Greenwich, CT
29/06 – 29/07
SG$1167/nighttotal: SG$35010 (30 )

Peaceful Pound Ridge Summer Retreat W/ Pool & 5 Bedrooms, 65 Min To Nyc

5 2
apartment , Scotts Corners
This Pound Ridge property, a generous 2-acre wooded estate, offers a secluded retreat near cultural sites such as the Caramoor Centre for Music and the Arts and The Glass House, located approximately 5.6 kilometres from Scotts Corners.
This spacious 372 square metre residence accommodates up to 10 guests across 5 bedrooms and 3 bathrooms, featuring a heated competition-sized swimming pool, a separate apartment, and zero-step access, with floor-to-ceiling windows opening onto a wrap-around deck for enjoying the surrounding nature.
Charming 2 Bedroom Cottage In Peaceful New Canaan - Pet Friendly! - Greenwich, CT
10 4 reviews
Greenwich, CT
07/08 – 12/08
SG$661/nighttotal: SG$3305 (5 )

Charming 2 Bedroom Cottage In Peaceful New Canaan - Pet Friendly!

2 2
cottage , New Canaan
This New Canaan cottage, located approximately 5km from both the New Canaan Historical Society and Steward House, offers easy access to local historical sites.
Sleeping up to eight guests, this two-bedroom, two-bathroom holiday home boasts a fully equipped kitchen, private balcony, garden, on-site playground, free Wi-Fi, and ample parking; games are also available.

Best Greenwich, CT holiday rentals with a pool

Among the 226 accommodations in Greenwich, CT, here are the 4 best rentals with a pool

Labrador Manor: Westchester County Home With Pool - Greenwich, CT
10 15 reviews
Greenwich, CT
30/08 – 30/09
SG$1403/nighttotal: SG$43493 (31 )

Labrador Manor: Westchester County Home With Pool

4 1
apartment , Port Chester
Labrador Manor is a charming historic house in Port Chester, just a 10-minute drive from the beach and 45 minutes from New York City. It consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
The house has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. The well-equipped kitchen, private pool, and spacious garden offer plenty of space for relaxation and entertainment, making it ideal for families or groups of friends.
Exquisite Bedford Lux Retreat. - Greenwich, CT
Greenwich, CT
10/09 – 19/09
SG$1554/nighttotal: SG$13986 (9 )

Exquisite Bedford Lux Retreat.

1 9
house , Bedford
House to rent. You will be based in Bedford.
Facilities and services include free parking, a barbecue and a washing machine. Take advantage of the terrace in this house!
Spacious Harbor Apt With Balcony - Greenwich, CT
Greenwich, CT
24/08 – 31/08
SG$555/nighttotal: SG$3885 (7 )

Spacious Harbor Apt With Balcony

1 2
apartment , Stamford
This Stamford South End flat is conveniently located 18km from Westchester County Airport, 19km from SUNY Purchase, and 21km from Manhattanville College.
The 76-square-metre self-catering apartment features a spacious layout with a separate bedroom and living room, accommodating up to 5 guests, and includes a private balcony, swimming pool access, and a fitness centre.
Modern Apt With Luxury Amenities - Greenwich, CT
Greenwich, CT
24/08 – 31/08
SG$524/nighttotal: SG$3668 (7 )

Modern Apt With Luxury Amenities

1 2
apartment , Stamford
This Stamford South End flat is situated less than 1.6km from the Museum of Black World War II History and Stamford Town Centre, and under 3.2km from Atlantic Square and the University of Connecticut Stamford campus.
The 65 square metre one-bedroom apartment sleeps three, offering a fully equipped kitchen, in-unit laundry, a swimming pool, fitness centre, and barbecue facilities, all within easy reach of Stamford Transportation Centre and Stamford Metro-North Train Station.

Frequently asked questions about holiday rentals in Greenwich, CT

  • What are the top family-friendly attractions in Greenwich, CT?

    The Greenwich Audubon Center is a great place for families, with nature trails and a variety of birdwatching opportunities. The Roger Sherman Baldwin Park is also a great option, with a playground, picnic areas, and a large pond.
  • What are the best Airbnb and vacation rentals in Greenwich, CT?

    The Safe House - High Tech Apt #3 - 4 Beds, The Safe House - High Tech Apt #2 - 3 Beds and The Safe House - High Tech Apt #1 - 2 Queen Beds are the most popular Airbnb and vacation rentals in Greenwich, CT among travelers.

  • When is the best time to book a vacation rental in Greenwich, CT?

    The best time to book a vacation rental in Greenwich is usually during the shoulder seasons, which are spring and autumn. You'll avoid the crowds and the prices will be lower than during the peak summer months.
  • What are the most popular Airbnbs in Greenwich, CT?

  • What events or festivals should visitors check out in and around Greenwich, CT?

    Greenwich has a few events that happen throughout the year, including the Greenwich Town Party, which is a huge street festival with music, food, and activities. The Greenwich International Film Festival is another popular event, which showcases independent films from around the world.
  • What are the best vacation rentals with a pool in Greenwich, CT?

  • What are the best budget-friendly activities in Greenwich, CT?

    There are a few budget-friendly activities in Greenwich, including taking a walk or bike ride along the waterfront. The Greenwich Library is also free to visit and has a variety of events and exhibits throughout the year.
  • What are the best rentals for families and kids in Greenwich, CT?

  • What are the best walking or cycling routes in Greenwich, CT?

    The Greenwich Rail Trail is a great option for walking or cycling, as it runs along the former New York, New Haven and Hartford Railroad line. For a more scenic route, try the Byram Shore Trail, which runs along the waterfront and offers stunning views of Long Island Sound.
  • What are the best rentals or Airbnbs with a jacuzzi in Greenwich, CT?

  • Are there pet-friendly attractions in Greenwich, CT?

    Yes, there are a few pet-friendly attractions in Greenwich, including the Greenwich Point Park, which has a dog park and a beach where dogs are allowed off-leash. The Greenwich Audubon Center also welcomes well-behaved dogs on its trails.
  • What are the benefits of choosing a vacation rental in Greenwich, CT?

    Vacation rentals in Greenwich offer more space and privacy than hotels. They're also often located in more residential areas, which can give you a better feel for the town. Plus, you can often find rentals with amenities that hotels don't offer, such as kitchens and laundry facilities.
  • What are the top sports attractions and facilities in Greenwich, CT?

    Greenwich is home to a number of sports attractions and facilities, including the Greenwich Country Club, which has a golf course and tennis courts. There's also the Greenwich Polo Club, which hosts polo matches throughout the summer.

Destinations nearby

Best Greenwich, CT holiday rentals with a balcony

3 Mi To Downtown: Spacious White Plains Home - Greenwich, CT
8.0 4 reviews
Greenwich, CT
24/08 – 31/08
SG$716/nighttotal: SG$5012 (7 )

3 Mi To Downtown: Spacious White Plains Home

5 2
house , Fairview
This spacious five-bedroom house in White Plains, Fairview, is situated 5km from White Plains city centre, offering easy access to Manhattanville College (9km), SUNY Purchase (11km), Iona College (18km), and Westchester County Airport (10km).
The 298 square metre property boasts three bathrooms, a fully equipped kitchen including a dishwasher and microwave, private parking, a terrace, garden, free Wi-Fi, and comfortably accommodates up to 25 guests.
New Beach Home Near Stamford Downtown/shippan - Greenwich, CT
8.0 2 reviews
Greenwich, CT
10/09 – 19/09
SG$1824/nighttotal: SG$16416 (9 )

New Beach Home Near Stamford Downtown/shippan

5 9
house , Stamford
This Stamford property is located a 7-minute walk from West Beach and 1.5 kilometres from Cummings Beach, close to the town centre and within easy reach of Stamford's waterfront attractions. The house has received very good user ratings, a good location rating, and an excellent cleanliness rating.
The house offers 5 bedrooms, 3 bathrooms, and a floor area of 204 square metres, comfortably accommodating up to 16 guests. It features a fully equipped kitchen, a terrace, a garden, a fitness centre, free parking, and an indoor play area, ensuring a comfortable and enjoyable stay for families and groups.
Stamford Grand Apartment - Greenwich, CT
9.6 13 reviews
Greenwich, CT
27/06 – 04/07
SG$659/nighttotal: SG$4613 (7 )

Stamford Grand Apartment

1 4
apartment , Stamford
This Stamford city centre apartment is ideally located a short walk from Stamford Town Centre, the Ferguson Library, and Stamford Center for the Arts, with Stamford Transportation Center and Stamford Metro-North Train Station approximately 1.2km away.
This 70 square metre dwelling boasts two bedrooms, one bathroom, sleeps four guests, and includes a private pool, in-unit laundry, and a fully equipped kitchen with fridge, microwave, and dishwasher.
Stylish 1br Apartment "Casita" - Greenwich, CT
10 1 review
Greenwich, CT
07/08 – 12/08
SG$233/nighttotal: SG$1165 (5 )

Stylish 1br Apartment "Casita"

1 2
apartment , Stamford
This flat in Stamford is located near Fort Stamford Park and The Glass House, with shops and the Merritt Parkway less than 1.6 kilometres away.
This one-bedroom flat accommodates up to three guests and features a fully equipped kitchen with a dishwasher, air conditioning, a balcony, an electric fireplace, and an in-unit washer and dryer.

Best Greenwich, CT holiday rentals with parking

H1 One Bedroom Apt Downtown Stamford - Greenwich, CT
8.2 5 reviews
Greenwich, CT
07/08 – 12/08
SG$218/nighttotal: SG$1090 (5 )

H1 One Bedroom Apt Downtown Stamford

1 2
apartment , Stamford
This Stamford city centre flat is conveniently located 21 kilometres from SUNY Purchase and 24 kilometres from Manhattanville College, offering easy access to local amenities.
The 21-square-metre apartment features one bedroom, one bathroom, sleeps five guests, and includes a fully equipped kitchen, private balcony, free Wi-Fi, and free private parking.
Comfort Meets Convenience Parking Gym Near Nyc - Greenwich, CT
Greenwich, CT
27/06 – 04/07
SG$873/nighttotal: SG$6111 (7 )

Comfort Meets Convenience Parking Gym Near Nyc

1 2
apartment , Stamford
This Stamford flat is located 19 kilometres from SUNY Purchase and Manhattanville College, and is conveniently located for travel to New York City and Westchester County Airport.
This 48 square metre apartment offers accommodation for up to 7 guests with a well-equipped kitchen, air conditioning, free WiFi, and on-site parking, with a fitness centre also available.
Comfy Cozy 2-bedroom Apartment In Great Location In Mamaroneck Ny Near Nyc - Greenwich, CT
10 2 reviews
Greenwich, CT
24/08 – 31/08
SG$211/nighttotal: SG$1477 (7 )

Comfy Cozy 2-bedroom Apartment In Great Location In Mamaroneck Ny Near Nyc

2 2
apartment , Mamaroneck
This Mamaroneck flat offers a prime location, situated close to Rockefeller State Park Preserve and Harbour Island Park, with convenient access to family attractions such as the Bronx Zoo and Rye Playland.
This property provides ample sleeping for up to eight guests with one king bed, two single beds, one double bed, and two sofa beds, complemented by amenities including air conditioning, Wi-Fi, and a kitchen equipped with a fridge and microwave, whilst outdoor pursuits like kayaking and hiking are readily available.
Bright&comfy 2bed/1ba In Quiet White Plains Duplex - Greenwich, CT
8.8 6 reviews
Greenwich, CT
24/08 – 31/08
SG$423/nighttotal: SG$2961 (7 )

Bright&comfy 2bed/1ba In Quiet White Plains Duplex

2 2
apartment , White Plains
This West Harrison home, situated within 3.2km of Pace University Law School and major shopping malls, offers convenient access to White Plains Hospital and the Westchester County Center, all within a 4.8km radius.
The two-bedroom, one-bathroom property sleeps four guests and includes a fully equipped kitchen, free on-site parking, and amenities such as a TV and dedicated workspace; nearby attractions include the White Plains Metro-North Railroad Station, a 29-minute walk away.
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