Best Holiday rentals and Airbnb offers in Greenwich, CT
10 1 review
Greenwich, CT
30/08 – 30/09
SG$295/nighttotal: SG$9145 (31 )
Cozy 2br Apartment In Greenwich With Driveway. Walk To Restaurants & Beach!
2 1
apartment , Greenwich
This 2-bedroom flat in Greenwich offers convenient access to local attractions, situated just a 5-minute drive from Greenwich Avenue and the Capitol Theatre, and within a 20-minute drive of Harbor Island Park and Greenwich Point Park. This accommodation provides Wi-Fi, air conditioning, and accommodates up to four guests, with essential toiletries and laundry facilities included, while nearby options include the Bruce Museum of Arts and Science, Rye Playland, and Chelsea Piers.
Greenwich, CT
27/06 – 04/07
SG$487/nighttotal: SG$3409 (7 )
Modern Apt Downtown
1 2
apartment , Stamford
This Stamford city centre flat is located 2.9km from West Beach and 17.7km from Westchester County Airport, offering easy access to local amenities and attractions. The 66 square metre one-bedroom apartment sleeps five, features a fully equipped kitchen with dishwasher, in-unit laundry, and access to an indoor swimming pool and fitness centre.
Greenwich, CT
30/06 – 31/08
SG$586/nighttotal: SG$36332 (62 )
Stylish Home And Cozy
1 2
apartment , Stamford
This Stamford flat is located in the Bedford district, offering proximity to downtown Stamford's shopping and attractions such as Chelsea Piers and the Bruce Museum of Arts and Science, with convenient rail access to London. This one-bedroom flat accommodates up to four guests and features complimentary high-speed Wi-Fi, air conditioning, an in-unit washer and dryer, access to a fitness centre, and a seasonal rooftop deck, with one free assigned covered parking space.
Greenwich, CT
27/06 – 04/07
SG$590/nighttotal: SG$4130 (7 )
Stylish 3br/2ba Retreat #3, Harbor Point Walk To Train, Cafes & Restaurants, City + Shore
3 4
apartment , Stamford
This three-bedroom flat in Stamford's South End offers prime positioning in Harbor Point, a 500-metre stroll from the waterfront and a 1.5-kilometre walk to Downtown Stamford's amenities, with the Stamford Metro-North Train Station just 700 metres away for a 50-minute express journey to Grand Central Terminal. This modern apartment accommodates up to eight guests with four full-sized beds, featuring a fully equipped kitchen with stainless steel appliances, high-speed WiFi, air conditioning, and complimentary parking for two vehicles, while local attractions such as Harbor Point boardwalk and Kosciuszko Park are within easy reach.
9.2 19 reviews
Greenwich, CT
07/08 – 12/08
SG$216/nighttotal: SG$1080 (5 )
Cozy 1bd Studio In Downtown Stamford
1 2
apartment , Stamford
This studio apartment is situated in the centre of Stamford, just a short walk from the town's historic market square and a range of shops and restaurants. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The self-contained apartment can accommodate up to two guests and features a comfortable living area with a well-equipped kitchen. Guests can enjoy access to a shared patio area, a laundry room, and free on-site parking.
Greenwich, CT
01/09 – 30/11
SG$176/nighttotal: SG$15840 (90 )
1 Bedroom Apartment In Dwtn Stamford W Laundry
1 2
apartment , Stamford
This one-bedroom flat in Downtown Stamford is situated 17 kilometres from Westchester County Airport and within 19 kilometres of the State University of New York at Purchase and Manhattanville College. This 21-square-metre flat accommodates up to three guests and offers a fully equipped kitchen with a microwave and fridge, in-unit laundry facilities, free WiFi, and free private parking.
10 15 reviews
Greenwich, CT
27/06 – 04/07
SG$351/nighttotal: SG$2457 (7 )
Twenty-one ! Boutique Stay (3f)
1 2
apartment , Greenwich
This Greenwich apartment is centrally located, a short walk from Greenwich Avenue and one block from Greenwich train station, offering easy access to I-95. The 550 sq ft (approximately 51 sq m) third-floor flat features a queen-size bed, full kitchen with dishwasher, air conditioning, and sleeps two guests, perfectly situated for exploring Greenwich's shops, restaurants, and transport links.
Greenwich, CT
15/10 – 26/10
SG$191/nighttotal: SG$2101 (11 )
Stamford : The Comfy Cove Hideout
1 2
apartment , Stamford
This one-bedroom flat is situated in the Cove - East Side - Shippan district of Stamford, offering easy access to E. Gaynor Brennan Golf Course, Chelsea Piers, and the Stamford Centre for the Arts, all within a 2 kilometre radius. This ground-floor dwelling features a private entrance, dedicated parking, a kitchenette with a two-burner stove, a 55-inch Smart TV, 1 Gbps internet, and a shared garden with a fire pit and outdoor dining area, accommodating up to three guests.
9.9 65 reviews
Greenwich, CT
07/08 – 12/08
SG$346/nighttotal: SG$1730 (5 )
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.
10 1 review
Greenwich, CT
27/06 – 04/07
SG$461/nighttotal: SG$3227 (7 )
Windows Of The Countryside
1 2
apartment , Greenwich
This stylish guest suite in Greenwich offers a tranquil retreat within a quiet residential setting, surrounded by beautiful natural scenery. This one-bedroom, one-bathroom flat accommodates two guests, featuring air conditioning, internet, and parking, located in a peaceful area ideal for unwinding.
9.8 45 reviews
Greenwich, CT
16/07 – 31/07
SG$634/nighttotal: SG$9510 (15 )
Beautiful Cottage In Greenwich Ct
1 2
house , Greenwich
This charming cottage is located just 5km from Westchester Airport and a 64km drive from Manhattan, offering a peaceful retreat in a quiet location. The property has received excellent ratings for cleanliness, location, and overall user experience. This cosy dwelling has one bedroom and one bathroom, comfortably accommodating two guests. Amenities include a fridge, air conditioning, parking, internet access, and the option for pets.
9.8 135 reviews
Greenwich, CT
15/10 – 26/10
SG$587/nighttotal: SG$6457 (11 )
Walk To Greenwich Ave [King Bed] Best Location
1 2
house , Greenwich
This charming duplex is situated in the Greenwich district, just a short walk from Greenwich Avenue, the train station, Whole Foods, and a variety of restaurants and nightlife options. It has received excellent ratings for user experience, location, and cleanliness. The property offers a spacious layout with multiple levels, comfortably accommodating up to six guests. It features modern amenities, including a fully equipped kitchen, updated appliances, high-speed Wi-Fi, Smart TVs, a fireplace, an outdoor BBQ and heater, and even an EV charger for an additional fee.
Best family friendly Greenwich, CT holiday rentals
Among the 226 accommodations in Greenwich, CT, here are the 4 best family friendly rentals
9.8 180 reviews
Greenwich, CT
15/10 – 26/10
SG$1157/nighttotal: SG$12727 (11 )
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.
9.9 46 reviews
Greenwich, CT
10/09 – 19/09
SG$692/nighttotal: SG$6228 (9 )
Luxurious 3br/2ba Modern Haven Downtown Stamford
1 9
apartment , Stamford
This three-bedroom Stamford apartment, a corner unit with city views, enjoys a downtown location near Stamford's top restaurants and shops, offering easy access to public transport. The 3-bedroom, 2-bathroom property sleeps up to nine guests, boasting an open-plan living space with a fully equipped kitchen, including a dishwasher, and a garden, along with parking and air conditioning.
9.8 26 reviews
Greenwich, CT
16/07 – 31/07
SG$815/nighttotal: SG$12225 (15 )
3br + Game Rm Abt 45min Drive Or Easy Train To Nyc
3 1
apartment , Port Chester
This Port Chester house, a 10-minute walk from the town centre, the Capitol Theatre, and the Port Chester train station offering direct access to Grand Central Terminal, provides convenient access to both New York City and Greenwich, Connecticut. Sleeping up to 11 guests in three bedrooms and two bathrooms, this property features a kitchen with fridge, freezer, microwave, and dishwasher, plus a garden, internet access, and parking for two cars; family reunions and similar gatherings are permitted with prior notification.
10 7 reviews
Greenwich, CT
10/09 – 19/09
SG$750/nighttotal: SG$6750 (9 )
Luxurious 3br/2ba Modern Haven Downtown Stamford
3 9
apartment , Stamford
This Stamford city centre apartment is conveniently located near Stamford Town Centre, offering easy access to restaurants, shops, and cultural attractions such as the Stamford Center for the Arts and the Fernando Luis Alvarez Gallery. The three-bedroom, two-bathroom dwelling boasts an open-plan layout, sleeping up to nine guests and features a fully equipped modern kitchen, air conditioning, and internet access.
Best Greenwich, CT holiday rentals with a pool
Among the 226 accommodations in Greenwich, CT, here are the 4 best rentals with a pool
Greenwich, CT
01/09 – 30/11
SG$297/nighttotal: SG$26730 (90 )
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.
Greenwich, CT
29/06 – 29/07
SG$1922/nighttotal: SG$57660 (30 )
Farmhouse Compound With Big Pool August Rental
1 2
apartment , Greenwich
This Merritt Farm, situated on prestigious Round Hill Road in Greenwich, Connecticut, offers stunning views and is conveniently located near Greenwich town centre. This six-bedroom, seven-bathroom property boasts a 40' x 20' heated saltwater swimming pool, expansive lawns, a private trail, and accommodates up to nine guests, perfect for families or groups seeking a luxurious country escape.
10 3 reviews
Greenwich, CT
10/09 – 19/09
SG$1535/nighttotal: SG$13815 (9 )
Walktowater+pool+fire Pit+grill+game Room
4 9
apartment , Stamford
This four-bedroom flat, offering accommodation for eight guests, is located in the private Davenport Point waterfront community on Long Island Sound, a short walk from the waterfront promenade, Prime, and Hinckley Yachts, with convenient access to downtown Stamford and its train service to New York City. The property features a saltwater swimming pool and spa, a spacious garden, a sunroom with backyard views, a primary suite with patio access, and a modern open-plan interior with a kitchen boasting peninsula seating and high-end appliances.
9.6 10 reviews
Greenwich, CT
16/07 – 31/07
SG$2650/nighttotal: SG$39750 (15 )
Historic 6-bdrm Tudor Estate W Pool/tennis Access
6 1
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?
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
Greenwich, CT
15/10 – 26/10
SG$414/nighttotal: SG$4554 (11 )
Super Luxury 1-bedroom Apartment With Amazing View Of New Roc City, With Extra
1 2
apartment , New Rochelle
This New Rochelle flat is located in Downtown Rochelle, placing it 12 kilometres from the Bronx Zoo and the New York Botanical Gardens, with New Roc City and Bay Plaza Shopping Centre within easy reach. This one-bedroom flat accommodates two guests and offers air conditioning, Wi-Fi, and access to an on-site fitness room.
Greenwich, CT
01/09 – 30/11
SG$2065/nighttotal: SG$185850 (90 )
595 M² House ∙ 5 Bedrooms ∙ 8 Guests
5 2
house , Stamford
House to rent for 8 guests. Your accommodation will be located in Stamford. Services and facilities include free parking, an iron and a garden. This house in Stamford is ideal for families.
10 1 review
Greenwich, CT
30/08 – 30/09
SG$159/nighttotal: SG$4929 (31 )
Stylish 1br Apartment "Casita"
1 1
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.
8.0 2 reviews
Greenwich, CT
15/10 – 26/10
SG$1567/nighttotal: SG$17237 (11 )
New Beach Home Near Stamford Downtown/shippan
5 2
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.
Best Greenwich, CT holiday rentals with parking
8.8 6 reviews
Greenwich, CT
27/06 – 04/07
SG$137/nighttotal: SG$959 (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).
10 3 reviews
Greenwich, CT
14/09 – 20/09
SG$4418/nighttotal: SG$26508 (6 )
Luxury Home With Amazing Water Views - Perfect For An Intimate Family Gathering
6 12
apartment , Mamaroneck
This apartment is located in the Sound Shore neighbourhood of Mamaroneck, within walking distance of restaurants, shops, and the Metro North train station. It has received excellent ratings for location, cleanliness, and user experience. This spacious home, covering 395 square metres and accommodating up to 10 guests, offers a range of amenities including a fully equipped kitchen, air conditioning, a terrace, a garden, a fitness centre, and parking. Guests can also enjoy access to a private office in the basement during the day.
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.
9.8 9 reviews
Greenwich, CT
30/08 – 30/09
SG$398/nighttotal: SG$12338 (31 )
Stamford Grand Apartment + Cozy Den
2 1
apartment , Stamford
This Stamford city centre flat is situated a short walk from Stamford Town Centre, Stamford Public Library, and Stamford Center for the Arts, with Stamford Transportation Center and the Metro-North Train Station approximately 1.2km away. The 72 square metre one-bedroom apartment sleeps five, featuring a fully equipped kitchen, in-unit laundry, a private pool, and a sofa bed; limited housekeeping is provided.