Greenwich, CT Vacation Rentals: house rentals & more

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.

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Find the best place to stay — Greenwich

Search 487 vacation rentals

Stayed Jun 2022

Fantastic house close to town

This house is wonderful and an easy 7 minute walk to Greenwich Ave. The back patio is lovely, and the large front porch is great for sunny afternoons. We used the third floor as an office but it easily could also work as a kids room. All in all thi...

Stayed May 2022

Very comfortable apartment

The apartment was lovely. It was well-appointed (good knives, pans, etc.). Beds, including the excellent sofa bed, were very comfortable. Very quiet, with excellent WiFi which helped my working there. Convenient to Everything. Communication with the ...

Stayed May 2022

Amazing home and even better host!

I stayed here for 3 weeks as I settled into Greenwich. The home was right off the main strip. Everything was in walking distance! There are so many restaurant choices right by the home. The house was cozy, clean, and bigger than we expected. Kim was ...

Stayed Apr 2022

Great place for a quick weekend away!

Our family from VA and GA all had a great stay. Everything was clean and tidy, beds were comfy! Lots of extra bedding, towels and extras like TP and paper towels! The kitchen’s spices were stocked and keurig coffee was plentiful amd much appreciated!

Stayed Feb 2022

Amazing stay!

So the house is way nicer in person. Super cute and in a quiet street. It has everything one could possibly need. If I could have stayed there longer I would. I will definitely be keeping this hidden gem in mind going forward for any friends or famil...

Stayed Jan 2022

Convenient, clean, and value!

This was one of the most convenient rental processes. Check-In—easy! Check-Out—easy! Parking—easy! For those visiting the local are with a car, this is a great way to live like a local. It’s so close to the border that it’s really close to New York ...

Stayed Dec 2021

Perfect home away from reno

Henri hosted us at 5 Idlewild for 6 months with our newborn, 3 year old non shedding dog and my husband and myself. There are two great bedrooms for kids and one large primary with lots of storage. We converted the dinning room area to a mini office ...

Stayed Nov 2021

Great stay

We were in town to see family over the Thanksgiving holiday. The accommodations were comfortable for us and our pet with easy access to all Greenwich has to offer. The owner lives in an attached property and was very nice, comuicative, and accommodat...

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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.

Activities

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…

Weather

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.