Westport, CT, USA

Westport, CT, USA

We found 203 vacation rentals — enter your dates for availability


Find the best place to stay — Westport

Where to stay near Westport, CT?

Our 2018 property listings offer a large selection of 203 vacation rentals near Westport. From 153 houses to 15 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.

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.

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 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.

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.

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.