Destination guide

Gatsby-inspired vacations

From its gleaming Tiffany's store to its historic theater, Westport lives up to its reputation as the Beverly Hills of the East. For decades the riverside town has lured a constant stream of artists, celebrities and well-heeled holidaymakers. In fact, Westport was supposedly the inspiration for F. Scott Fitzgerald's The Great Gatsby. Not to mention Ira Levin's The Stepford Wives. Want to join the tribe? With Westport vacation rentals, you can unlock access to a host of exclusive properties in Westport's most coveted neighborhoods. Chances are, you'll soon be enjoying a G&T with your neighbor.

Things to do

A slice of Broadway at the Westport Country Playhouse

Founded in 1931, the Westport Country Playhouse is one of Connecticut's most prestigious performing arts venues. Over the decades, the lovingly converted barn has staged hundreds of productions, overseen by local legends Paul Newman and Joanne Woodward. Check the website to see what's on. The Westport Arts Center takes a more casual approach, with colorful exhibits, theatrical performances, kids' classes and more. For a dose of sunshine, head to Sherwood Island State Park. Calm surf, shallow water and grassy picnic spots make its sandy beaches perfect for families.


Boutique hopping

Get your bearings with a stroll along Westport's upmarket main street. It's lined with an irresistible collection of designer boutiques, breezy cafes and upmarket seafood restaurants. For an in-depth introduction to the town, check out what's on at the Westport Historical Society. Based at the 1795 Bradley-Wheeler House, they offer walks and guided tours run by friendly locals. Westport enjoys a scenic setting by the Saugatuck River which means there are plenty of opportunities to swim, fish and paddle. Snag a riverfront Westport vacation rentals property and you'll have exclusive access to the water.


A summer sanctuary

With long days and lashings of sunshine, summer is high season in Westport. Beautiful weather makes it a fantastic time to relax on the beach, paddle in the river or kick back with a good book and a glass of wine. Planning a summer getaway? From luxurious family-sized estates to chic summer cottages, Westport vacation rentals make it easy to slip into holiday mode. While fall may not be warm enough to swim or sunbathe, the crisp temperatures and fiery foliage make it a great time to enjoy outdoor pursuits.

Natural features

Escape to Long Island Sound

Set on Long Island Sound, Westport is part of Connecticut's Fairfield County region. It's just 50 miles northeast of New York City and is a haven for Big Apple locals. To the south is Sherwood Island State Park, which lures vacationers with a 1.5-mile stretch of golden sand. On a clear day, you may be able to make out the distant New York City skyline. For a glimpse of the county's agricultural legacy, head to the Wakeman Town Farm Sustainability Center. The homestead spotlights the importance of organic, sustainable and community-oriented farming.

How to get there

Transportation to and around Westport

Fly into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), the closest airport, located 11.3 mi (18.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Danbury, CT (DXR-Danbury Municipal), which is 17.5 mi (28.2 km) away.

Where to stay around Westport?

Our 2019 property listings offer a large selection of 170 vacation rentals near Westport. From 139 Houses to 11 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 Westport for a holiday or a weekend are on HomeAway.

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

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

  • Compo Beach: 286 vacation rentals
  • Westport Historical Society: 279 vacation rentals
  • Burying Hill Beach: 293 vacation rentals
  • Westport Country Playhouse: 288 vacation rentals
  • Levitt Pavilion: 281 vacation rentals

But there are many other points of interest around Westport 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 Westport?

Yes, of course. HomeAway has 139 Houses in Westport. Our other popular types of vacation rentals in Westport include:

  • Condos/Apartments: 11 rentals available
  • Cottages: 9 rentals available
  • Studios: 10 rentals available

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

Can I find a vacation rental with pool in Westport?

Yes, you can select your preferred vacation rental with pool among our 37 vacation rentals with pool available in Westport. Please use our search bar to access the selection of vacation rentals available.