Compare Vacation Rentals & Airbnb in Greenwich, CT

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Greenwich, CT vacation rentals
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226 Rentals and Airbnb in Greenwich, CT

Best family friendly Greenwich, CT vacation rentals

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

Peaceful Pound Ridge Summer Retreat W/ Pool & 5 Bedrooms, 65 Min To Nyc - Greenwich, CT
Greenwich, CT
29/06 – 29/07
$1269/nighttotal: $38070 (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.
Stylish Loft W/parking Near Nyc + Hospital - Greenwich, CT
9.9 65 reviews
Greenwich, CT
24/08 – 31/08
$278/nighttotal: $1946 (7 )

Stylish Loft W/parking Near Nyc + Hospital

1 2
apartment , Stamford
This charming cottage is located in Stamford, just a short distance from the city centre and close to attractions like the Stamford Town Centre and the Stamford Museum & Nature Center. The property has received excellent ratings for its cleanliness, location, and overall experience.
This cosy home sleeps up to four guests and features a fully equipped kitchen, a dedicated workstation, and two Smart TVs. Guests can also enjoy a private patio, a fenced yard, and two parking spaces.
Comfort Next To The Byram River With Gazebo - Greenwich, CT
9.8 8 reviews
Greenwich, CT
16/07 – 31/07
$346/nighttotal: $5190 (15 )

Comfort Next To The Byram River With Gazebo

1 2
resort , Greenwich
This stylish Greenwich apartment, situated in a quiet Byram cul-de-sac with direct access to the Byram River, offers a tranquil retreat near Greenwich's natural beauty.
The one-bedroom, one-bathroom flat sleeps four guests and features a private patio, gazebo with Wi-Fi, indoor/outdoor cooking facilities, and proximity to opportunities for fishing and kayaking on the Byram River.
3 Bedroom Home  Free Parking  Great For Families, Friends & Groups - Greenwich, CT
Greenwich, CT
21/06 – 26/06
$999/nighttotal: $4995 (5 )

3 Bedroom Home Free Parking Great For Families, Friends & Groups

3 2
apartment , White Plains
This three-bedroom, two-bathroom flat in White Plains offers convenient access, being a 3-minute drive from the Westchester County Center and a 4-minute drive from The Westchester Mall, with parking available.
This property accommodates up to 16 guests and features a fully equipped kitchen, in-unit laundry, free Wi-Fi, air conditioning, and a barbecue grill, with nearby attractions including the Rockefeller Archive Center and Performing Arts Centre at Purchase College.

Best Greenwich, CT vacation rentals with a pool

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

Upscale Downtown 2br | Lux Amenities | Laundry - Greenwich, CT
8.8 3 reviews
Greenwich, CT
24/08 – 31/08
$630/nighttotal: $4410 (7 )

Upscale Downtown 2br | Lux Amenities | Laundry

2 2
apartment , White Plains
This apartment is conveniently located in the city centre of White Plains, close to the train station and a short drive from the Hudson River, making it an ideal base for exploring both the city and surrounding countryside. The apartment is ideal for families or groups, offering 2 bedrooms and 2 bathrooms with a floor area of 93 square metres and a guest capacity of 5.
The apartment is well-equipped with modern amenities, including a fully equipped kitchen, air conditioning, a swimming pool, a garden and parking. There is also a concierge service, high-speed internet, laundry facilities and a range of activities to enjoy, such as a fitness centre, a game room and a children's playroom.
Labrador Manor: Westchester County Home With Pool - Greenwich, CT
10 15 reviews
Greenwich, CT
21/06 – 26/06
$1475/nighttotal: $7375 (5 )

Labrador Manor: Westchester County Home With Pool

1 2
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.
Historic 6-bdrm Tudor Estate W Pool/tennis Access - Greenwich, CT
9.6 10 reviews
Greenwich, CT
21/06 – 26/06
$2164/nighttotal: $10820 (5 )

Historic 6-bdrm Tudor Estate W Pool/tennis Access

1 2
apartment , Stamford
This six-bedroom apartment is ideally located in central Stamford, just a short walk from both E. Gaynor Brennan Golf Course and Stamford Hospital. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious flat is perfect for large groups or families, offering a comfortable and well-equipped living space. Guests can enjoy a range of amenities, including a swimming pool, tennis court, sauna, and barbecue facilities, as well as a fully-equipped kitchen, a terrace, and a garden.
Modern Studio | Upscale Amenities | Kitchen & Laundry - Greenwich, CT
Greenwich, CT
21/06 – 26/06
$664/nighttotal: $3320 (5 )

Modern Studio | Upscale Amenities | Kitchen & Laundry

2 2
studio , White Plains
This White Plains apartment is ideally situated near the Galleria mall, Westchester County Center, and White Plains Hospital, all within a 2.4km radius, offering easy access to the Metro-North Railroad station (0.96km away).
This 39 square metre flat features two bedrooms, one bathroom, sleeps three, and includes a fully equipped kitchen, free Wi-Fi, a washing machine, and on-site amenities such as a swimming pool, fitness centre, and concierge service.

Frequently Asked Questions about vacation rentals in Greenwich, CT

  • Which neighborhood in Greenwich, CT should you consider for a vacation rental?

    If you're looking for a vacation rental in Greenwich, you'll find plenty of options in the Cos Cob neighbourhood, which is close to the waterfront and has a good selection of restaurants and shops.
  • 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.

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

    Greenwich is great for families. The Greenwich Audubon Center is a fantastic place to explore nature, and the Roger Sherman Baldwin Park offers plenty of space for kids to run around.
  • What are the most popular Airbnbs in Greenwich, CT?

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

    The best time to book a vacation rental in Greenwich is during the shoulder seasons, from April to May or September to October, when the weather is still pleasant but the crowds are smaller.
  • What are the best vacation rentals with a pool in Greenwich, CT?

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

    A stroll along the Greenwich waterfront is a great free activity, and the town's many parks, such as Roger Sherman Baldwin Park, offer plenty of opportunities for picnics and outdoor activities.
  • What are the best rentals for families and kids in Greenwich, CT?

  • What are the best restaurants with local dishes in Greenwich, CT?

    For a taste of local fare, try the Greenwich Grille, which serves up classic American dishes with a focus on fresh, seasonal ingredients. The Chatham, with its New England-inspired menu, is another great option.
  • What are the best rentals or Airbnbs with a jacuzzi in Greenwich, CT?

    The best vacation rentals or Airbnb with a jacuzzi in Greenwich, CT are Safe Quiet Greenwich 2 -5 Bd+massage+jacuzzi, Greenwich Home With Pool and Spacious Home In Downtown Greenwich.

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

    The Greenwich Rail Trail is a paved path that follows the old New York, New Haven and Hartford Railroad line, offering a scenic route for walking or cycling. The Mianus River Gorge Preserve is another great option for a nature walk.
  • Are there pet-friendly attractions in Greenwich, CT?

    Many of Greenwich's parks, such as Roger Sherman Baldwin Park and Binney Park, are dog-friendly, and there are also several pet-friendly restaurants and shops in town.
  • What are the benefits of choosing a vacation rental in Greenwich, CT?

    Staying in a vacation rental gives you more space and privacy than a hotel, and you can often find rentals that are located in more convenient locations, such as close to the beach or downtown.
  • What are the top sports attractions and facilities in Greenwich, CT?

    Greenwich is home to the Greenwich Country Club, which has a championship golf course, and the Greenwich Polo Club, which hosts polo matches during the summer months. The town also has several public parks with tennis courts and other sports facilities.

Destinations nearby

Best Greenwich, CT vacation rentals with a balcony

New Beach Home Near Stamford Downtown/shippan - Greenwich, CT
10 24 reviews
Greenwich, CT
10/09 – 19/09
$1947/nighttotal: $17523 (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.
Lavish 1 Bed Apt + Rooftop & Gym - Downtown Stamford - Greenwich, CT
8.0 3 reviews
Greenwich, CT
30/08 – 30/09
$380/nighttotal: $11780 (31 )

Lavish 1 Bed Apt + Rooftop & Gym - Downtown Stamford

1 1
apartment , Stamford
This Downtown Stamford apartment, a short walk (less than 1 km) from the Stamford Town Centre, Fernando Luis Alvarez Gallery, and Stamford Public Library, offers convenient access to cultural attractions and transport links.
The 64 square metre self-catering flat features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, a private balcony, and access to a fitness centre, spa and parking.
Waterview House Walking Distance From Cove Beach-5 Mins To Downtown-only 40 Min To Nyc - Greenwich, CT
9.8 179 reviews
Greenwich, CT
21/06 – 26/06
$1430/nighttotal: $7150 (5 )

Waterview House Walking Distance From Cove Beach-5 Mins To Downtown-only 40 Min To Nyc

5 2
house , Stamford
This Stamford house is located a short walk from Cove Beach and just 5 kilometres from the city centre, offering easy access to both the beach and the city's attractions. The property has received excellent ratings for location, cleanliness and user experience.
This spacious five-bedroom house is ideal for large families or groups. The home is equipped with modern amenities, including a fully equipped kitchen, a terrace with sea views, an indoor play area, and a tennis court.
Flex Comfort Apts Of Greenwich #3 - Greenwich, CT
9.4 63 reviews
Greenwich, CT
10/09 – 19/09
$395/nighttotal: $3555 (9 )

Flex Comfort Apts Of Greenwich #3

2 3
apartment , Greenwich
This top-floor flat in Greenwich, CT, offers an excellent user rating and is situated 1.6 kilometres from downtown Greenwich and 3.2 kilometres from Port Chester, with convenient access to the Greenwich Metro-North station.
This two-bedroom, one-bathroom apartment accommodates up to four guests and features a well-equipped kitchen, air conditioning, a terrace, garden, private parking for two vehicles, and shared access to laundry facilities and a BBQ area.

Best Greenwich, CT vacation rentals with parking

Stamford Bohemian By Harborpoint Downtown &Train - Greenwich, CT
8.8 6 reviews
Greenwich, CT
27/06 – 04/07
$147/nighttotal: $1029 (7 )

Stamford Bohemian By Harborpoint Downtown &Train

1 2
house , Stamford
This Stamford dwelling is located in Downtown Stamford, a 16-minute walk from Cummings Beach and 19 kilometres from Westchester County Airport.
The one-bedroom property, sleeping up to three guests, offers a fully equipped kitchen, garden, parking, air conditioning, Wi-Fi, and use of a barbecue (propane and cleaning supplied by guests).
Cozy Stay Near Capitol Theatre/downtown  Very Walkable! - Greenwich, CT
10 31 reviews
Greenwich, CT
10/09 – 19/09
$385/nighttotal: $3465 (9 )

Cozy Stay Near Capitol Theatre/downtown Very Walkable!

2 3
apartment , Port Chester
This apartment is located in Port Chester, just a kilometre from the Capitol Theatre, Metro North train station, and the town centre, making it a convenient base for exploring the area. It has received excellent reviews from previous guests.
The second floor flat sleeps up to four guests and has a private entrance with parking for three cars. It is fully equipped with amenities including a kitchen, washer and dryer, and a comfortable living space.
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views - Greenwich, CT
Greenwich, CT
14/09 – 20/09
$3237/nighttotal: $19422 (6 )

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

6 12
apartment , Greenwich
This six-bedroom lakefront house is located in a prestigious Greenwich neighbourhood, offering uninterrupted views of an 11-acre lake and a private dock, less than 16 kilometres from New York City.
This spacious residence accommodates up to 12 guests and features internet, air conditioning, a kitchen with a fridge, microwave oven, and dishwasher, as well as private parking and a garden, with nearby attractions including the Fernando Luis Alvarez Gallery and the Bruce Museum of Arts and Science.
Exquisite Bedford Lux Retreat. - Greenwich, CT
8.2 6 reviews
Greenwich, CT
10/09 – 19/09
$1683/nighttotal: $15147 (9 )

Exquisite Bedford Lux Retreat.

3 9
house , Bedford
This Bedford property, situated 24 kilometres from both SUNY Purchase and Manhattanville College and 19 kilometres from Westchester County Airport, offers convenient access to local colleges and transport links.
This three-bedroom, two-bathroom house boasts 186 square metres of floor space, accommodating up to 19 guests with amenities including a jacuzzi, sauna, terrace, garden, free parking and Wi-Fi, plus nearby hiking trails and an on-site mini-market.
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