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.


Retail therapy on The Avenue

Manhattan may steal the spotlight, but Greenwich also knows a thing or two about high street shopping. Along The Avenue you'll find a host of high-end shops and upscale restaurants. Think luxury jewelers, artisan florists and curated clothing boutiques. Historic Old Greenwich is a fantastic place for a stroll, luring visitors with 19th-century shopfronts and independent stores. Want to stay local? From New England mansions to Tudor-style cottages, Greenwich vacation rentals put you in the heart of the historic district.


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

Traveling to and around Greenwich

The nearest airport is in White Plains, NY (HPN-Westchester County), located 2.9 mi (4.6 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 22.3 mi (36 km) away.

Where to stay around Greenwich?

Our 2019 property listings offer a large selection of 284 vacation rentals near Greenwich. From 207 Houses to 39 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Greenwich for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Greenwich?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Greenwich:

  • Midtown: 985 vacation rentals
  • Old Greenwich: 124 vacation rentals
  • Rowayton: 18 vacation rentals
  • Downtown: 18 vacation rentals
  • Cove - East Side - Shippan: 23 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Greenwich?

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

  • Putnam Cottage: 315 vacation rentals
  • Stanwich Club: 273 vacation rentals
  • Flinn Gallery at Greenwich Library: 332 vacation rentals
  • Bruce Museum of Arts and Science: 334 vacation rentals
  • Audubon Center: 293 vacation rentals

But there are many other points of interest around Greenwich listed on HomeAway 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. HomeAway has 207 Houses in Greenwich. Our other popular types of vacation rentals in Greenwich include:

  • Condos/Apartments: 39 rentals available
  • Estates: 4 rentals available
  • Studios: 38 rentals available

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

Can I find a vacation rental with pool in Greenwich?

Yes, you can select your preferred vacation rental with pool among our 63 vacation rentals with pool available in Greenwich. Please use our search bar to access the selection of vacation rentals available.

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