Discover a selection of 487 vacation rentals in Greenwich, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $142 per night, and houses and condos are popular options for a stay in Greenwich. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Greenwich
Destination guide

A haven for New Yorkers

From its upmarket shopping to its historic estates, Greenwich lives up to its reputation as one of the East Coast's most affluent towns. For decades, it has lured a constant stream of celebrities, investors and well-heeled New Yorkers. Greenwich sits in Fairfield County and is dotted with elegant hillside mansions, country clubs and a handful of sun-drenched beaches. The train ride from Grand Central takes just 40 minutes, which makes Greenwich vacation rentals eternally popular with New Yorkers in search of sun, sand and fresh air.

Things to do

Sun-drenched days at Greenwich Point Park

Escape the rat race and head to Greenwich Point Park, an uninhabited peninsula fringed by beautiful sandy beaches. On a clear day, Tod's Point offers sweeping views of the distant NYC skyline. In summer, it's a great place to sign the kids up for a sailing lesson. Why not enjoy the New England high life as a family getaway, with a Greenwich vacation rental? From BBQs to Bloody Marys, a private sun deck will sweeten the deal. Take shelter from uncooperative weather at the Bush-Holley House Museum. Housed in an 18th-century cottage, it showcases a fantastic collection of American Impressionism.


Beachcombing and beautiful buildings in Greenwich

You won't want to make for the pearly beaches of the Connecticut coast until you've toured the handsome buildings of Old Greenwich. Joining a history walk that takes in all that and the Revolutionary War sights of Cos Cob is a great idea, while others will prefer to get their retail fix down the chic drag of Greenwich Avenue. Then it's time to hit the sands, unless – of course – you've managed to bag one of the coveted Greenwich vacation rentals that overlook the lapping Long Island Sound – then the sea's just on the doorstep…


Explore Greenwich's summer events calendar

Crowds peak in the summer, when Greenwich is brimming with locals and New Yorkers alike. Greenwich throws a lively summer events calendar, with outdoor concerts, farmers markets, Fourth of July fireworks and more. Fall brings clear skies, crisp temperatures are fiery foliage. It's too cold to swim but the weather is ideal for beach walks, brunches, shopping and golf. Winter can get chilly but it's a great excuse to rug up for a windswept walk on the beach or enjoy a cozy night by the fire.

Natural features

Connect with nature in Long Island Sound

While it may tempt visitors with its boutiques and restaurants, Greenwich doesn't scrimp on nature. The town is fringed by 4 Long Island Sound beaches, including scenic Greenwich Point. With a long sandy beach, scenic walking trails and grassy picnic spots it's a great place to enjoy the sunshine. A handful of islands sit just offshore and serve as a haven for birdlife. Much of Great Captain's Island is occupied by a bird sanctuary, which is famous for its population of great blue herons.

How to get there

Transportation to and around Greenwich

The nearest airport is in Westchester County Airport (HPN), located 4.9 mi (7.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into John F. Kennedy Intl. Airport (JFK), which is 27.6 mi (44.4 km) away.

How many vacation rentals are available around Greenwich, CT?

Our 2022 property listings offer a large selection of 487 vacation rentals around Greenwich. From 343 house rentals to 112 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Greenwich?

Vrbo offers a large selection of vacation rentals near lovely places in Greenwich. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Greenwich Avenue Historic District: 468 vacation rentals
  • Putnam Cottage: 471 vacation rentals
  • Flinn Gallery at Greenwich Library: 474 vacation rentals
  • Bruce Museum of Arts and Science: 474 vacation rentals
  • Griffith E. Harris Golf Course: 444 vacation rentals

But there are many other points of interest around Greenwich listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Greenwich?

Yes, of course. Vrbo has 343 Houses in Greenwich. Our other popular types of vacation rentals in Greenwich include:

  • Condos/Apartments: 112 rentals available
  • Cottages: 19 rentals available
  • Townhouses: 10 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cabins and more.

Can I find a vacation rental with pool in Greenwich?

Yes, you can select your preferred vacation rental with pool among our 98 vacation rentals with pool available in Greenwich. Please use our search bar to access the selection of vacation rentals available.