Photo by Kate Persad

Old Greenwich vacation rentals

We found 302 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 15 homes and other vacation rentals in Old Greenwich that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

Houses

Houses
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Friendly Old Greenwich will entice you

The beaches and other outdoor surroundings create an inviting atmosphere in Old Greenwich. This welcoming and romantic city entices travelers with its restaurants and shopping. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Old Greenwich

Are you hoping to discover things to do in the city? Venture out of your vacation home and check out everything that makes Old Greenwich a fun spot to vacation. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Chelsea Piers (3.3 mi / 5.4 km)
  • Rye Playland (6.9 mi / 11.1 km)
  • Stanwich Club (7.8 mi / 12.5 km)
  • Bayville Adventure Park (8 mi / 12.9 km)
  • Norwalk Maritime Aquarium (9.4 mi / 15.1 km)
  • Theodore Roosevelt Sanctuary (11 mi / 17.7 km)

Exploring the natural landscape of Old Greenwich

Whether you're an active traveler or just want to take in the scenery, Old Greenwich is a great place to spend some time outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Greenwich Point Park (1.6 mi / 2.6 km)
  • West Beach (2.5 mi / 4 km)
  • Cove Island Park (3.7 mi / 6 km)
  • Hawthorne Beach (5.4 mi / 8.7 km)
  • Calf Pasture Beach (10 mi / 16.1 km)
  • Harbor Island Park (10.3 mi / 16.5 km)

Transportation options to and around Old Greenwich

Fly into Westchester County Airport (HPN), the closest airport, located 7.9 mi (12.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Farmingdale, NY (FRG-Republic), which is 21.6 mi (34.7 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Old Greenwich?

According to our research, houses are considered the most popular vacation rental type in Old Greenwich. But that goes without saying, everyone's idea of an epic stay isn't going to be the same. Vrbo has vacation homes of all shapes and sizes, so you're sure to find the best fit for your needs.

How much does it cost to rent a vacation rental in Old Greenwich?

Length of stay, season and property type are among the factors that can affect the price of a vacation home. Simply add your travel dates to find your perfect escape. From cozy country cottages to expansive luxury villas, all Vrbo vacation rentals offer amazing value.

How much does it cost to rent a beach house in Old Greenwich?

Prices for beach houses in Old Greenwich differ depending on the style and size of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use the filters to tailor your search results by amenities, ratings, nearby activities and more.

Are there pet-friendly vacation rentals in Old Greenwich?

Yes. You can pick from nine vacation rentals that allow pets in Old Greenwich. Plenty of our pet-friendly vacation rentals come with a garden for your furry pal to run around in, complimentary treats, special dog beds and proximity to parks and green space. Apply the "Pets allowed" filter to find your place on Vrbo.

Can I rent a house with a pool in Old Greenwich?

Tick the "pool" box in our filter tool and select from three houses with private pools in Old Greenwich on Vrbo. Morning swim, sunset soak or midnight dip? Leisure time is your call when your vacation property has a swimming pool.

What are popular rental amenities in Old Greenwich?

An electric car charging station, a nearby waterfront and a fireplace are rated the most popular rental amenities in Old Greenwich. Whether you're heading away by yourself, with your other half or a group of family members, Vrbo will help you find a vacation home that matches your tastes with all the extras you're looking for.

Are there large group vacation rentals in Old Greenwich?

Old Greenwich has three vacation homes that can accommodate 10 or more guests. These stays come with the space you need to enjoy good times with friends and family.

Are there vacation rentals in Old Greenwich that welcome kids?

Bring the entire family together for fun-filled adventures in Old Greenwich at one of our nine family-friendly vacation rentals. Many of these stays come with conveniences that are just perfect for getaways with children, including full kitchens, bunk beds and patios. Simply check the "Properties good for families" filter and choose your favorite.

What are the top attractions for families in Old Greenwich?

Keeping the kids amused during your Old Greenwich vacation is simple with these top family-friendly attractions:

  • West Beach
  • Hawthorne Beach
  • Stamford Historical Society Museum

Are there vacation rentals with WiFi in Old Greenwich?

You can pick from two vacation rentals with WiFi in Old Greenwich. If you'd like to disconnect from daily life on your escape, but still need to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Old Greenwich?

Work out your travel dates and then use our filter tool to see vacation rentals with ac in Old Greenwich on Vrbo. With eight air-conditioned properties to choose from here, you can enjoy a cool and comfortable break.

How old do you have to be to rent a vacation rental in Old Greenwich?

The minimum required age is usually 16, 18 or 21. It can differ from one property to another on Vrbo, so look at the rules of your preferred Old Greenwich vacation rental before making a booking.