Holiday Rentals in Greenwich, CT

226 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Greenwich, CT holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Hotel Alternative, Close To Town, Clean And New - Greenwich, CT
9.4 19 reviews
Greenwich, CT
30/08 – 30/09
SG$681/nighttotal: SG$21111 (31 )

Hotel Alternative, Close To Town, Clean And New

1 1
apartment , Greenwich
This Greenwich hotel, offered as "Hotel Alternative, Close To Town, Clean And New", is conveniently located near Greenwich's beaches and attractions, with proximity to public transport but precise distances unspecified.
The three-bedroom, two-bathroom property sleeps six, features a fully equipped kitchen, top-of-the-line appliances, and offers flexible sleeping arrangements including a queen bed, convertible trundle bed, and potential twin beds, plus cribs and highchairs available on request.
Private Single Fam, Walk 2 Train/ Theater- Dogs Ok - Greenwich, CT
10 1 review
Greenwich, CT
04/09 – 06/09
SG$1059/nighttotal: SG$2118 (2 )

Private Single Fam, Walk 2 Train/ Theater- Dogs Ok

1 8
apartment , Greenwich
This three-bedroom flat is located on the Byram River in Greenwich, Connecticut, offering convenient pedestrian access to Port Chester's dining and entertainment options, the Capitol Theatre, and within walking distance of the Museum of Bruce Park and Greenwich Avenue's shops.
This family-friendly property welcomes pets and features a private, enclosed garden with a patio and barbecue, a shared riverfront deck, air conditioning, Wi-Fi, and on-site parking for up to eight guests.
Family-friendly 2br With Parking Near Nyc + Hospital - Greenwich, CT
10 29 reviews
Greenwich, CT
16/07 – 31/07
SG$347/nighttotal: SG$5205 (15 )

Family-friendly 2br With Parking Near Nyc + Hospital

2 2
apartment , Stamford
This Stamford flat is conveniently located within a 2.4km walk of both E. Gaynor Brennan Golf Course and Stamford Hospital, placing you close to key attractions and services. Guests have consistently rated this property as excellent, highlighting its comfortable and well-equipped nature.
The two-bedroom apartment comfortably accommodates up to four guests, making it ideal for families or groups of friends. The property offers a fully equipped kitchen, a private outdoor space with a balcony and garden, as well as convenient access to amenities such as parking and a barbecue area.
Newro Chic Retreat- 3 Bdrms 30 Min To Nyc - Greenwich, CT
9.6 9 reviews
Greenwich, CT
10/09 – 19/09
SG$496/nighttotal: SG$4464 (9 )

Newro Chic Retreat- 3 Bdrms 30 Min To Nyc

3 3
apartment , New Rochelle
This New Rochelle apartment is conveniently located a short 1.6km walk from New Roc City and Monroe College, and under 5km from Iona College and Glen Island Park, offering easy access to public transport with New Rochelle Station a 2km walk away.
The 93 square metre apartment sleeps five guests, boasting three bedrooms, one bathroom, a fully equipped kitchen including oven and microwave, free on-site parking, complimentary Wi-Fi, and in-unit entertainment including a Smart TV, games, and books.

Best Greenwich, CT holiday 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
16/07 – 31/07
SG$603/nighttotal: SG$9045 (15 )

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.
Stunning 1-bed, 1-bath With Breathtaking Views & Luxury Finishes - Greenwich, CT
Greenwich, CT
27/06 – 04/07
SG$390/nighttotal: SG$2730 (7 )

Stunning 1-bed, 1-bath With Breathtaking Views & Luxury Finishes

1 4
apartment , New Rochelle
This New Rochelle apartment, ideally situated near the waterfront and offering easy access to Randall's Island Park, provides a convenient base for exploring the city.
The one-bedroom flat boasts an open-plan layout, sleeping up to four guests and includes a chef's kitchen with stainless steel appliances, a spa-like bathroom, and access to a swimming pool, spa and fitness centre; nearby recreational opportunities include golfing, swimming and ice skating.
Luxury 1br In Downtown | Full Kitchen | W&d - Greenwich, CT
10 4 reviews
Greenwich, CT
10/09 – 19/09
SG$553/nighttotal: SG$4977 (9 )

Luxury 1br In Downtown | Full Kitchen | W&d

1 3
apartment , White Plains
This one-bedroom flat is located in downtown White Plains, a short walk from the Galleria at White Plains shopping mall and a 14-minute walk from Westchester County Center. The apartment is conveniently situated near restaurants, shops, and public transport, making it a great base for exploring the area.
The 48 square meter flat comfortably sleeps up to three guests and features a separate living room, dining area, and bedroom. The apartment comes with a range of amenities including a fully equipped kitchen, a private terrace, a shared pool, a fitness centre, and a playground.
Historic 6-bdrm Tudor Estate W Pool/tennis Access - Greenwich, CT
9.6 10 reviews
Greenwich, CT
10/09 – 19/09
SG$2391/nighttotal: SG$21519 (9 )

Historic 6-bdrm Tudor Estate W Pool/tennis Access

6 9
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.

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.
595 M² House ∙ 5 Bedrooms ∙ 8 Guests - Greenwich, CT
Greenwich, CT
30/08 – 30/09
SG$2389/nighttotal: SG$74059 (31 )

595 M² House ∙ 5 Bedrooms ∙ 8 Guests

5 1
house , Stamford
House for up to 8 guests. You will stay in Stamford.
Facilities and services include a kitchen, a dish washer and a freeze. This house in Stamford also has air conditioning!
Lavish 1 Bed Apt + Rooftop & Gym - Downtown Stamford - Greenwich, CT
8.0 3 reviews
Greenwich, CT
24/08 – 31/08
SG$413/nighttotal: SG$2891 (7 )

Lavish 1 Bed Apt + Rooftop & Gym - Downtown Stamford

1 2
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
SG$1315/nighttotal: SG$6575 (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.

Best Greenwich, CT holiday rentals with parking

3br Home  1.5 Bath  Garage Parking  White Plains  Near Nyc - Greenwich, CT
Greenwich, CT
04/09 – 06/09
SG$798/nighttotal: SG$1596 (2 )

3br Home 1.5 Bath Garage Parking White Plains Near Nyc

3 8
apartment , White Plains
This three-bedroom flat in White Plains offers convenient access to local attractions, with the Westchester County Center a 13-minute walk (approximately 1.04 kilometres) away, The Westchester Mall a 3-minute drive (approximately 0.48 kilometres), and the White Plains Metro-North train station a 7-minute walk (approximately 0.56 kilometres).
This family-friendly apartment accommodates up to 16 guests and features a well-equipped kitchen with an oven and fridge, air conditioning, on-site covered parking, complimentary Wi-Fi, and an in-unit washer and dryer.
Midcentury Modern Zenhouse Sculptor Studio - Greenwich, CT
9.7 3 reviews
Greenwich, CT
16/07 – 31/07
SG$747/nighttotal: SG$11205 (15 )

Midcentury Modern Zenhouse Sculptor Studio

1 2
studio , Stamford
This Midcentury Modern ZenHouse Sculptor Studio apartment is situated in Stamford, Connecticut, approximately 22.5 kilometres from both the State University of New York at Purchase and Manhattanville College, and Westchester County Airport.
The 111-square-metre self-catering apartment features a spacious layout with one bedroom, one bathroom, and can accommodate up to three guests, offering amenities such as a fully equipped kitchen with dishwasher, a private terrace, garden, swimming pool, tennis court, parking, and complimentary Wi-Fi.
Stylish Home With Free Parkingza - Greenwich, CT
Greenwich, CT
27/06 – 04/07
SG$851/nighttotal: SG$5957 (7 )

Stylish Home With Free Parkingza

1 4
apartment , Stamford
This one-bedroom flat in Stamford's Glenbrook-Belltown district is situated an 8-minute walk from Glenbrook Park and a 4-minute drive from Chelsea Piers.
This accommodation offers Wi-Fi, air conditioning, a fully equipped kitchen, and an in-unit washer and dryer, accommodating up to four guests.
Spacious 3 Bedroom House  Free Driveway Parking  Perfect For Families & Groups - Greenwich, CT
Greenwich, CT
04/09 – 06/09
SG$869/nighttotal: SG$1738 (2 )

Spacious 3 Bedroom House Free Driveway Parking Perfect For Families & Groups

3 8
apartment , White Plains
This three-bedroom, two-bathroom flat in White Plains is a 12-minute walk from The Westchester Mall and a 3-minute drive from the Westchester County Center, with Pelham Bay Park located 17 minutes and Glen Island Park 16 minutes away by car.
This pet-friendly accommodation offers air conditioning and internet, comfortably accommodating up to 16 guests with essential toiletries provided, and is conveniently situated near Lenoir Preserve and Rockefeller State Park Preserve for outdoor pursuits.
©2026 cozycozy.com