Discover a selection of 187 vacation rentals in Westport, 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 kitchens. Prices start at $99 per night, and houses and cottages are popular options for a stay in Westport. Either way, you'll find a rental for everyone's needs.
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.

How many vacation rentals are available around Westport, CT?

Our 2020 property listings offer a large selection of 187 vacation rentals around Westport. From 134 house rentals to 13 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a beach property in Westport?

Rising every morning to glorious ocean views and the sound of waves on the shoreline. This is the stuff vacation fantasies are made of! Vrbo has 36 vacation homes by the beach. Alternatively, you may be searching for something different. Vrbo has no lack of choices, including:

  • 28 water-view vacation rentals.
  • 24 shore-front vacation rentals.
  • 22 seaside vacation rentals.

Can I rent a house in Westport?

Our house vacation rentals are real properties for real travelers. Offering loads of space and privacy, they're perfect for those who want to experience life like a local. There are 119 options currently listed on Vrbo. Prices start at $95 per night. If that doesn't match your posse's taste, we've got a range of other property types to pick from, such as:

  • Hotel: 27 vacation homes. Prices start from $49 per night.
  • Apartment: 14 vacation homes. Prices start from $130 per night.
  • Cottage: 10 vacation homes. Prices start from $221 per night.

Can I stay in Westport in a large group?

Sometimes it can be tough finding time to catch up with your closest family and friends. A group trip is an ideal way to be reunited. If you were hoping to kick back together, Vrbo has options to suit. 30 house vacation homes are available. Presently, they're the leading choice here for big groups. Rental accommodations around here that are just right for bigger groups include:

  • On the lookout for vacation homes that can fit 8 people? We have 31 that will be suitable. The prices start from $195 per night.
  • If you've got 6 in your party, you'll be pleased to discover that there are 31 vacation homes perfect. Prices begin at just $150 a night.
  • On a trip away with a group of 10? We've got 18 vacation homes that will suit. Prices start from $290 per night.

Your whole squad will be in good hands when you organize your Westport escape with us!

Where are the cheapest rentals in Westport?

Friends become our chosen family. Catch up with those who truly matter and organize a value-for-money stay with Vrbo. When it comes to getting your hands on a fantastic deal, your first port of call ought to be Lordship. Here, Vrbo has 3 rentals at an average price of $215 a night. You'll find another 8 Vrbo rentals waiting to be booked in or around Old Greenwich. The average price here is $224 per night.