Discover a selection of 500 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 $117 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.

What are the top vacation rentals in or near Greenwich?

Whatever vacation experience you're seeking, you'll find a rental in or around Greenwich that fits you like a glove. These are some of our favorites:

  • "Greenwich Back Country Farm House" is a favorite with guests. Around 2 miles from Greenwich, it has 5 bedrooms and plenty of amenities to help you feel at home, including WiFi and tennis.
  • "Back Country Estate With Pool - Greenwich Ct" is another top pick, offering 5 bedrooms, a travel crib, a nearby marina and more. It's around 2 miles from Greenwich.

For even more great options, use the search bar at the top of the page to find the perfect Greenwich vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Greenwich?

If you've been busier than a squirrel in a nut factory, you deserve to escape for a couple of glorious days. Clock off early on Friday and head for one of these weekend getaways in or near Greenwich:

  • "Greenwich Hotel Alternative / Boutique Living" is ideal for a long weekend of fun and relaxation. It offers useful amenities, such as a hair dryer and an ice maker, and is located about 3 miles to the south of Greenwich.
  • Or, toss a few clothes in your overnight bag and make a beeline for "Brand New Walk To Train, Downtown Fully Loaded". This popular property is around 3 miles southeast of Greenwich and offers a living room and children's games.

Can I find studio apartments for rent in and around Greenwich?

Studio apartments may be small in size, but they sure do pack a punch when it comes to convenience and location. Make yourself comfortable at one of these welcoming studio apartments in and around Greenwich:

  • Get away on your own or take a few pals to "Best Location - New Renovation". You'll have lots of amenities at your fingertips, including a TV and a hair dryer.
  • "Walker's Paradise Steps From Greenwich Ave" is another wonderful stay, offering all you could need for a dream Greenwich retreat. Convenient amenities here include cable/satellite TV services and off-street parking options.

Can I find short term rentals in or near Greenwich?

Whether you're looking for a chic apartment or a house big enough to fit the family, you'll find the perfect place on Vrbo. Enjoy a mini break at one of these favorites in or near Greenwich:

  • Within easy reach of central Greenwich, "Best Location - New Renovation" rolls out the welcome mat for short-term guests. When you're not holed up in your comfortable digs, get out and discover all the fun stuff around you.
  • Another terrific option is "Greenwich, Ct Hotel Alternative Completely Renovated High End Townhouse". Round up your favorite people and enjoy a comfy stay near the heart of Greenwich.

What are the best romantic weekend getaways in or near Greenwich?

Whether spent in a log cabin or a beach house, a romantic weekend getaway is one of the best ways to spice up your relationship. Whisk your special someone off for a few days at one of these enticing escapes in or near Greenwich:

  • Slip away on Friday for a couple of passion-filled evenings at "Greenwich Back Country Farm House". Located approximately 2 miles from Greenwich, this place comes with lots of nice touches, like a fireplace and a swimming pool.
  • Otherwise, spend a few days sipping wine and canoodling at "Back Country Estate With Pool - Greenwich Ct", around 2 miles from Greenwich. Beauty services and a nearby bay will help set the mood.

What are the best large group vacation rentals in or near Greenwich?

Big groups mean huge fun. They also mean finding a place that'll effortlessly fit your crew. Check out our large group vacation rentals in or around Greenwich and get everybody together under the one roof:

  • Providing privacy, comfort and space, you'll get your guests' tick of approval at "New Greenwich House With Nyc Flair". Up to 12 people can stay at this retreat which has 5 bedrooms, a nearby river and a garden. This group favorite is around 4 miles to the southeast of Greenwich.
  • Invite up to 12 of your favorite people to "The Deluxe Fred 2 Floor 6 Br" and fill its spaces with love and laughter. This top option has 6 bedrooms and is around 7 miles to the east of central Greenwich. It's crammed with features to keep your group happy and comfortable, including a firepit and a kitchen.

What are the best houses for rent with a pool in or near Greenwich?

Nothing says fun times like a pool does. Pump up your inflatable unicorn and check out these houses in or near Greenwich that come with this must-have amenity:

  • Switch to vacay mode at "Greenwich Back Country Farm House", where your top priority will be relaxing by the pool. Amenities such as a fridge and a dishwasher help make this getaway a guest favorite.
  • Alternatively, unpack your bags at "New Greenwich House With Nyc Flair". Along with a refreshing pool, you'll also have use of a TV and a microwave oven.

Greenwich has a humid subtropical climate, with average summertime temperatures hovering between 70 ºF and 80 ºF. But you don't have to wait until summer to visit! Take a look at the search bar at the top of the page and adjust the filters to find the perfect Greenwich vacation rental and plan your escape for whatever season you like.

What are the best large family vacation rentals in or near Greenwich?

You'll always have more fun sharing those precious memories with the people you care about the most. Whether you're organizing a family catch-up or taking time out with your best friends, we'll have a large vacation rental to suit your style. Here are two of our best in and around Greenwich:

  • Sleeping up to 10 guests in 5 bedrooms, "Greenwich Back Country Farm House" is the perfect place to spend quality time with the family. This getaway is 2 miles to the north of Greenwich and has creature comforts that include a dishwasher and a fridge.
  • "Back Country Estate With Pool - Greenwich Ct" is another popular option. It's around 2 miles to the north of Greenwich, has 5 bedrooms and accommodates up to 8 guests. Handy amenities here include nearby birdwatching activities and a porch.

If you're hoping to visit some family-friendly attractions in the area, you have plenty of choice. Norwalk Maritime Aquarium, Greenwich Avenue and Beardsley Zoo offer fun for both kids and grown-ups.

What are the best large houses to rent with indoor pools in or near Greenwich?

Nothing says "glamorous getaway" like having a pool inside your house. Pack your swimwear and enjoy a dip in the privacy of one of these roomy vacation homes in or near Greenwich:

  • With 5 bedrooms sleeping up to 10 people, "Greenwich Back Country Farm House" is the ideal place to take a break with close friends. Take advantage of this retreat's host of amenities, such as a swimming pool and a fireplace.
  • In addition to its fancy indoor pool, "Apartment Al Pescatore In Mal" comes with a kitchen and a swimming pool. It has 5 bedrooms that can cater for up to 10 people, so you can bring the extended family along.

Use the search bar at the top of the page and adjust the filters to find more impressive Greenwich vacation rental options for your next big getaway.

Are there one-bedroom vacation rentals in or near Greenwich?

Often located in prime positions due to their compact size, a one-bedroom rental is a wise pick if you're traveling solo or with one other person. Here's a taste of Vrbo's range in or near Greenwich:

  • Good things really do come in small packages, and "2 Bedroom Peaceful, Convenient Downtown Greenwich Unit" is a fabulous example of this. This one-bedroom property is not far from the central streets and includes amenities like a garden and a kitchen.
  • Or maybe "Quiet Convenient Downtown Large Sunny Studio" matches your style better. Another conveniently located one-bedroom option, this place comes with a garden, a kitchen and more.