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Best Vacation rentals and Airbnb offers in Greenwich, CT
10 29 reviews
Greenwich, CT
07/16 – 07/31
$270/nighttotal: $4050 (15 )
Family-friendly 2br With Parking Near Nyc + Hospital
2 2
apartment , Stamford
This Stamford apartment is conveniently located within a 15-minute walk of both E. Gaynor Brennan Golf Course and Stamford Hospital, offering easy access to both recreation and medical care. Guests have consistently rated this rental as "excellent," highlighting its comfortable and convenient amenities. This two-bedroom home comfortably accommodates up to four guests and features a fully equipped kitchen, a private outdoor space, and a garden, making it ideal for families and groups. Amenities include a private yard, a balcony, a barbecue grill, and a smoke-free environment.
Greenwich, CT
07/16 – 07/31
$320/nighttotal: $4800 (15 )
2 Mi To Nyc Train: Wfh-friendly Greenwich Apt!
1 2
apartment , Greenwich
This Greenwich apartment is conveniently located approximately 2.2 miles from Purchase College and 2.5 miles from Capitol Theatre. This pet-friendly residence offers air conditioning, a full kitchen with a microwave, a private patio, on-site barbecue grills, and complimentary self-parking.
10 31 reviews
Greenwich, CT
09/10 – 09/19
$275/nighttotal: $2475 (9 )
Cozy Stay Near Capitol Theatre/downtown Very Walkable!
2 3
apartment , Port Chester
This Port Chester apartment is conveniently located within walking distance of downtown, the Capitol Theatre, and the Metro North train station, making it easy to explore the area's attractions. Guests consistently rate this apartment as "excellent" for its comfort, amenities, and location. The apartment is a spacious second-floor unit with two bedrooms, one bathroom, and a comfortable living area that can accommodate up to four guests. The apartment comes fully equipped with a kitchen, laundry facilities, and a private entrance with on-site parking for up to three cars.
10 1 review
Greenwich, CT
06/27 – 07/04
$609/nighttotal: $4263 (7 )
Elegant Home
1 4
apartment , Stamford
This Stamford apartment offers convenient access to educational institutions like SUNY Purchase and Manhattanville College, both 12 miles away, and Westchester County Airport, located 11 miles from the property. This 520 square foot residence accommodates up to 7 guests, featuring a fully equipped kitchen with a dishwasher and oven, air conditioning, complimentary Wi-Fi, and on-site parking, while remaining a non-smoking environment.
10 1 review
Greenwich, CT
08/30 – 09/30
$123/nighttotal: $3813 (31 )
Stylish 1br Apartment "Casita"
1 1
apartment , Stamford
This Stamford apartment is located near bus route 133, within walking distance of shops and restaurants, and less than 1 mile from the Merritt Parkway. This one-bedroom, one-bathroom unit accommodates up to three guests and features a fully equipped kitchen with a dishwasher, air conditioning, a private balcony, an electric fireplace, and an in-unit washer and dryer.
9.8 8 reviews
Greenwich, CT
06/27 – 07/04
$579/nighttotal: $4053 (7 )
Stamford Grand Apartment + Cozy Den
2 4
apartment , Stamford
This downtown Stamford apartment is steps from Stamford Town Center, a 5-minute walk from the Ferguson Library and Stamford Center for the Arts, offering easy access to shops, restaurants, and public transportation. This 780-square-foot unit features one bedroom, one bathroom, a fully equipped kitchen with a dishwasher, in-unit laundry, a sofa bed accommodating up to five guests, and access to a private pool.
Greenwich, CT
07/16 – 07/31
$323/nighttotal: $4845 (15 )
Cozy Pleasantville Retreat Unit 2 2 Bedroom Apts
1 2
apartment , Pleasantville
This Pleasantville rental unit is located under a 15-minute walk from the Jacob Burns Film Center Theater and Media Arts Lab, and within 3 miles of Rockefeller State Park Preserve and St John's River Side Hospital. This pet-friendly apartment offers complimentary Wi-Fi, a refrigerator, a coffee maker, a ceiling fan, and an iron/ironing board, with Smart TVs available for entertainment.
Greenwich, CT
07/03 – 07/31
$355/nighttotal: $9940 (28 )
Private Apt Close To Train
1 2
apartment , Stamford
This Stamford apartment rental, "Private Apt Close to Train," is conveniently located 1.6 miles from West Beach and 12 miles from Westchester County Airport, offering easy access to public transportation and nearby colleges. The 720-square-foot unit features one bathroom, sleeps five guests, and includes a fully equipped kitchen with a dishwasher, in-unit laundry, air conditioning, free Wi-Fi, and access to an on-site fitness center.
10 11 reviews
Greenwich, CT
07/16 – 07/31
$749/nighttotal: $11235 (15 )
Hot New 2 Bedroom Walk To Train
1 2
apartment , Greenwich
This Greenwich, London apartment rental sleeps four guests in two bedrooms and two bathrooms, offering convenient access to Greenwich attractions—exact proximity requires a specific address. The 2-bedroom, 2-bathroom unit includes a kitchen, air conditioning, internet, and parking; further details on amenities and square footage are needed.
10 142 reviews
Greenwich, CT
09/04 – 09/06
$628/nighttotal: $1256 (2 )
Bright & Modern Victorian In Ny Suburbs
1 8
apartment , Mamaroneck
This 3-bedroom apartment is located in Mamaroneck, just a short distance from the marina and village, offering easy access to both the vibrant downtown and the city of New York. The apartment has excellent ratings for location, cleanliness, and user experience. The apartment comfortably accommodates up to 8 guests and includes a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. You can enjoy amenities like air conditioning, parking, and internet access, as well as an outdoor space for relaxing.
Greenwich, CT
06/27 – 07/04
$662/nighttotal: $4634 (7 )
Stylish Home With Free Parkingza
1 4
apartment , Stamford
This one-bedroom condo in Stamford's Glenbrook-Belltown district is a 4-minute drive from Chelsea Piers and an 8-minute walk from Glenbrook Park. This pet-friendly apartment accommodates up to 4 guests and features air conditioning, free Wi-Fi, a full kitchen, and an in-unit washer and dryer, with workspace amenities and proximity to the Stamford Center for the Arts and Stamford Town Center.
10 1 review
Greenwich, CT
06/27 – 07/04
$362/nighttotal: $2534 (7 )
Luxurious 1br Downtown Stamford
1 2
apartment , Stamford
This luxurious one-bedroom Stamford apartment is centrally located in Downtown Stamford, conveniently close to Westchester County Airport (11 miles), Manhattanville College (13 miles), and SUNY Purchase (12 miles). This 830-square-foot unit sleeps five guests and boasts a fully equipped kitchen, private patio, fireplace, free parking, and access to a spa and fitness center.
Best Greenwich, CT vacation rentals with a balcony
9.8 67 reviews
Greenwich, CT
06/21 – 06/26
$1771/nighttotal: $8855 (5 )
Waterfront Retreat Center For Health & Wellness
8 2
apartment , New Rochelle
This waterfront vacation rental is located in New Rochelle, just a short distance from New Roc City, Monroe College, Glen Island Park, and Iona College. The property has received excellent user ratings and offers a comfortable and convenient stay for families and groups. This spacious home features 7 bedrooms, 6 bathrooms, and can accommodate up to 20 guests. Enjoy the outdoor amenities, including a garden, barbecue grills, and a terrace, as well as the convenience of free WiFi, a DVD player, and a fully equipped kitchen.
Greenwich, CT
09/10 – 09/19
$1208/nighttotal: $10872 (9 )
Exquisite Bedford Lux Retreat.
1 9
house , Bedford
House listing. You will be in Bedford. Facilities and services include air conditioning, a swimming pool and free parking.
This Downtown Stamford apartment rental is conveniently located within a 10-minute walk of the Stamford Town Center, Stamford Public Library, and Fernando Luis Alvarez Gallery. The 690-square-foot unit features one bedroom, one bathroom, sleeps two guests, and includes a full kitchen, private balcony, free Wi-Fi, and access to a fitness center and spa.
8.0 4 reviews
Greenwich, CT
08/24 – 08/31
$557/nighttotal: $3899 (7 )
3 Mi To Downtown: Spacious White Plains Home
5 2
house , Fairview
This White Plains house rental, located three miles from downtown White Plains and six miles from Westchester County Airport, offers easy access to Manhattanville College, SUNY Purchase, Iona College, and the Palisades Center Mall. This 3,210-square-foot property boasts five bedrooms, three bathrooms, and accommodates up to 25 guests, featuring a fully equipped kitchen, air conditioning, a terrace, a garden, parking, and free Wi-Fi.
Our Favorite Family-Friendly Vacation Rentals in Greenwich, CT
Find the perfect family vacation rental or Airbnb in Greenwich, CT with plenty of room to spread out near local beaches.
Greenwich, CT
07/16 – 07/31
$401/nighttotal: $6015 (15 )
Luxury 1 Bed Unit In Greenwichgym/parking/patio
1 2
apartment , Greenwich
This apartment in Greenwich offers a sophisticated living experience with premium hardwood floors, quartz countertops, and a 55-inch Smart TV in an open-concept layout, ideal for two guests. Enjoy convenient access to a state-of-the-art gym, stylish common areas, a conference room, and complimentary coffee and snacks, with ample natural light and modern stainless steel appliances completing the fully equipped kitchen.
10 1 review
Greenwich, CT
08/30 – 09/30
$863/nighttotal: $26753 (31 )
Family-friendly Stamford Downtown Delight
4 1
apartment , Stamford
This Stamford apartment rental is conveniently located an 11-minute walk from the Stamford Center for the Arts and a 15-minute walk from Stamford Town Center. This 1910-square-foot family-friendly dwelling boasts four bedrooms, three bathrooms, and comfortably accommodates eight guests, featuring amenities such as on-site parking, in-unit laundry, and a fully equipped kitchen.
10 86 reviews
Greenwich, CT
08/30 – 09/30
$825/nighttotal: $25575 (31 )
Gameroom, Backyard + Pool! 5m To Train + Downtown
1 1
apartment , Stamford
This family-friendly Cape Cod apartment is situated near downtown Stamford, CT, 8 minutes from Downtown/UConn and 7 minutes from the Train Station. This apartment has received excellent ratings for its location, cleanliness, and user experience. It has four bedrooms, three bathrooms, and can accommodate up to eight guests. It features a private fenced-in backyard with a lounging pool and grill, a game room with a foosball table and 55" Roku TV, and high-speed 1 Gig fiber-optic internet.
10 1 review
Greenwich, CT
09/10 – 09/19
$422/nighttotal: $3798 (9 )
Modern 2 Bdr, Harbor Point #2 Walk To Train, Restaurants, City + Shore
2 3
apartment , Stamford
This 2-bedroom, 1-bathroom apartment in Stamford's South End district is a 6-minute walk from Stamford Train Station, an 11-minute walk to the Stamford Second World War African American Museum, and a 2-minute drive to Stamford Town Center. This unit accommodates up to 4 guests and includes a kitchenette with a fridge and microwave, complimentary Wi-Fi, air conditioning, and is close to Mianus Park and Houston Preserve.
Frequently Asked Questions about vacation rentals in Greenwich, CT
What are the top family-friendly attractions in Greenwich, CT?
Greenwich has a lot to offer families! The Greenwich Audubon Center is a great place to learn about nature, the Maritime Aquarium at Norwalk is a short drive away and has tons of sea life, and the Roger Sherman Baldwin Park is perfect for a picnic or playing frisbee.
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 in the shoulder seasons, spring and fall. You'll avoid the summer crowds and the prices will be lower.
What are the most popular Airbnbs in Greenwich, CT?
What are the best budget-friendly activities in Greenwich, CT?
Greenwich has plenty of free and budget-friendly activities. You can walk or bike along the scenic waterfront, visit the free exhibits at the Bruce Museum, or have a picnic at Greenwich Point Park.
What are the best vacation rentals with a pool in Greenwich, CT?
What are the best restaurants with local dishes in Greenwich, CT?
For a taste of local cuisine, try the Lobster Shack at the Greenwich Point Park for fresh seafood, or the Greenwich Pizza for a classic New England pizza experience. You can also find great Italian food at the Italian Center.
What are the best rentals for families and kids in Greenwich, CT?
What are the best walking or cycling routes in Greenwich, CT?
Greenwich has some beautiful walking and cycling routes. The Greenwich Loop is a popular choice, taking you along the waterfront and through the town center. You can also explore the trails at the Greenwich Audubon Center.
What are the best rentals or Airbnbs with a jacuzzi in Greenwich, CT?
Are there pet-friendly attractions in Greenwich, CT?
Yes, Greenwich is very pet-friendly. Greenwich Point Park is a great place to walk your dog, and many restaurants have outdoor seating that welcomes pets. Check out the Greenwich Dog Park for off-leash fun.
Destinations nearby
Best Greenwich, CT vacation rentals with parking
9.6 5 reviews
Greenwich, CT
08/24 – 08/31
$206/nighttotal: $1442 (7 )
Modern Luxe 1br Apt In Downtown Stamford
1 2
apartment , Stamford
This Stamford apartment is located in Downtown, a short walk from shopping, restaurants, and bars, and within a 3-minute drive of I-95 and a 4-minute drive from Stamford Metro North Station, making it easy to explore the city and commute to NYC. It has received excellent guest ratings for its amenities and location. The apartment has one bedroom and one bathroom, accommodating up to three guests. Amenities include a fully equipped kitchen, in-unit laundry, air conditioning, parking, a fitness center, and rooftop access, providing everything you need for a comfortable and enjoyable stay.
8.0 2 reviews
Greenwich, CT
06/21 – 06/26
$855/nighttotal: $4275 (5 )
New Beach Home Near Stamford Downtown/shippan
5 2
house , Stamford
This Stamford house is situated in the New Beach district, within walking distance of West Beach and a short drive from Downtown Stamford and Shippan Point. It offers stunning panoramic views of Long Island Sound and the Stamford cityscape. The house has very good user ratings and a good location rating. With 5 bedrooms and 3 bathrooms spread over 2200 square feet, the house can comfortably accommodate up to 16 guests. It features a modern kitchen, air conditioning, a terrace with garden views, an outdoor fireplace, a fitness center, and private parking.
Greenwich, CT
06/27 – 07/04
$662/nighttotal: $4634 (7 )
Stylish Home With Free Parking
1 4
apartment , Stamford
This one-bedroom rental is in Stamford's Bedford neighborhood, offering proximity to restaurants, Stamford Town Center, Springdale Shopping Center, Mianus Park, and Houston Preserve, with convenient train access to NYC. This pet-friendly apartment accommodates up to four guests and includes a private washer/dryer, a 55-inch TV with streaming services, a fully equipped kitchen, air conditioning, covered parking, and access to an on-site fitness center and seasonal rooftop.
8.8 4 reviews
Greenwich, CT
07/03 – 07/31
$683/nighttotal: $19124 (28 )
Penthouse Perfection With Unmatched Skyline Views
2 2
apartment , Stamford
This Stamford penthouse, located 11 miles from Westchester County Airport and within a 25-30 mile radius of Manhattanville College and SUNY Purchase, offers easy access to area attractions. This 1,010-square-foot luxury rental boasts two bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, free parking, a patio, a fitness center, spa, and accommodates up to 10 guests.
Neighborhoods and points of interest in Greenwich, CT
Search Vacation Rentals with Swimming Pool in Greenwich, CT
A vacation rental with a pool in Greenwich, CT is the perfect amenity to complement your time spent by the water.
Greenwich, CT
08/24 – 08/31
$330/nighttotal: $2310 (7 )
Downtown Studio Br | Near Metronorth Station
2 2
studio , White Plains
This White Plains apartment rental is ideally situated near the Galleria at White Plains, Westchester County Center, and White Plains Hospital, a short walk from the Metro-North Railroad station. The 420-square-foot unit features two bedrooms, one bathroom, sleeps three guests, and includes a fully equipped kitchen, free Wi-Fi, and on-site amenities such as a fitness center, swimming pool, and concierge service.
Greenwich, CT
08/30 – 09/30
$1858/nighttotal: $57598 (31 )
595 M² House ∙ 5 Bedrooms ∙ 8 Guests
5 1
house , Stamford
Vacation rental for up to 8 guests. You will stay in Stamford. Facilities and services: rooms suitable for events, a terrace and a washing machine. Enjoy a swimming pool in this house in Stamford!
9.0 2 reviews
Greenwich, CT
07/16 – 07/31
$469/nighttotal: $7035 (15 )
Modern 2br In Downtown| Clubhouse + Gym | Parking
2 2
apartment , White Plains
This White Plains apartment rental is conveniently located a 6-minute walk from the White Plains Metro-North Railroad Station, providing easy access to NYC, and within a 15-minute walk of the Galleria at White Plains and Westchester County Center. The 1000-square-foot three-bedroom, two-bathroom unit sleeps five guests and features a fully equipped kitchen, free WiFi, on-site fitness center, swimming pool, and concierge service.
10 2 reviews
Greenwich, CT
08/24 – 08/31
$2050/nighttotal: $14350 (7 )
Family Getaway.commuter's Dream.weddings&events.content House.luxury Smart Home
4 2
apartment , Larchmont
This charming vacation rental is located in Larchmont, just a short drive from the New Roc City entertainment complex and Harbor Island Park. The surrounding area offers a quaint and peaceful ambiance, perfect for a relaxing getaway. This spacious home features 4 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests. Enjoy modern amenities like air conditioning, a fully equipped kitchen, and a washer and dryer, making your stay comfortable and convenient.
Search Coastal Vacation Rentals near Greenwich, CT
Discover charming seaside vacation rentals in Greenwich, CT near the coast. Browse our favorite coastal picks to find your perfect beach-town match.
Greenwich, CT
08/24 – 08/31
$431/nighttotal: $3017 (7 )
Spacious Harbor Apt With Balcony
1 2
apartment , Stamford
Greenwich, CT
08/24 – 08/31
$431/nighttotal: $3017 (7 )
Modern Apartment In Harbor Point
1 2
apartment , Stamford
9.6 38 reviews
Greenwich, CT
08/24 – 08/31
$319/nighttotal: $2233 (7 )
Close To New York City-old Greenwich Surf Shack Ii
1 2
apartment , Greenwich
8.0 1 review
Greenwich, CT
06/21 – 06/26
$4626/nighttotal: $23130 (5 )
Gorgeous Water Front House / Huge Garden & Sea Access
9 2
house , Mamaroneck
Browse Luxury Vacation Rentals in Greenwich, CT
Discover the best of the coast with a luxury vacation rental in Greenwich, CT, offering sophisticated rooms and prime locations.
