Westport Vacation Rentals, Connecticut: Whole House to Yourself

Discover a selection of 54 homes and other vacation rentals in Westport that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the amenities you need and want for your stay, which might include parking and a garden. You'll be sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Find properties near top attractions in Westport

Compo Beach

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Westover Castle -Majestic in The Forest

Sleeps 24 · 9 bedrooms · 6+ bathrooms

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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.

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.

Exploring the natural features in Westport

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Westport is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

Compo Beach (2.6 mi / 4.2 km)
Calf Pasture Beach (4.2 mi / 6.7 km)
Fairfield Beach (5.5 mi / 8.9 km)
Penfield Beach (6.1 mi / 9.8 km)
Jennings Beach (6.3 mi / 10.1 km)
Seaside Beach (8.2 mi / 13.2 km)

Transportation options to and around Westport

The nearest airport is in Westchester County Airport (HPN), located 18.7 mi (30.1 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is 25.8 mi (41.6 km) away.

If you prefer train travel, make your way to Westport Station or Green's Farms Station to see more of the city.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Westport?

The most desirable types of vacation rentals in Westport are houses. After something a little different? Vrbo has a variety of options to match our guests' needs, so you'll see vacation homes in lots of shapes and sizes. The ideal home away from home is waiting for you — snap up yours today.

How much does it cost to rent a vacation rental in Westport?

Property type, length of stay and time of year are some factors that can influence the price of a vacation home. Simply add your travel dates to find your perfect match. From cozy chalets to sprawling villas, all Vrbo vacation rentals provide incredible value.

How much does it cost to rent a beach house in Westport?

Prices for beach houses in Westport differ depending on the style and size of the property and time of year you're traveling. Simply enter your travel dates into Vrbo and the number of guests to view your options and prices. From there you can use our filters to refine your search by ratings, amenities and more.

Are there pet-friendly vacation rentals in Westport?

Pack a suitcase for your pooch because Westport has 48 vacation rentals that put out the welcome mat to pets. Let your furriest pal enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check our "Pets allowed" filter box.

Can I rent a house with a pool in Westport?

Mark the "pool" box in our filter tool and you can choose from 20 houses with private pools in Westport on Vrbo. Lazy soak or ball games and races? How you spend your leisure time is up to you when your vacation home comes with its own swimming pool.

What are popular rental amenities in Westport?

When it comes to rental amenities that guests prefer in Westport, an electric car charging station, a nearby waterfront and a sauna rank the highest. With Vrbo vacation rentals, there are choices to suit your taste and style, whether you're planning to get away with family members, friends or even pets.

Are there large group vacation rentals in Westport?

Westport has 11 vacation rentals that can fit 10 or more people. These stays come with plenty of space to share good times with loved ones.

Are there vacation rentals in Westport that welcome kids?

Westport has 47 family-friendly vacation rentals to choose from. And booking a stay that welcomes kiddos is a breeze with Vrbo's "Properties good for families" filter. As well as having the whole place to yourselves, you'll enjoy access to amenities and perks such as living rooms, kitchens and pools.

What are the top attractions for families in Westport?

There are plenty of awesome things to do and see with the family in Westport, such as:

Compo Beach
Norwalk Maritime Aquarium
Jennings Beach

Are there one-bedroom vacation rentals in Westport?

Yes, you can take your pick from five one-bedroom rentals in Westport. Whether you're looking for a cozy cottage or a fancy condo, Vrbo's one-bedroom properties are perfect if you don't require a huge amount of space. One of the major perks of having your own digs? You won't ever have to share your adventure with strangers.

Can I find two-bedroom vacation rentals in Westport?

Take off with your loved ones and relax in total privacy and comfort in one of the three two-bedroom vacation properties Westport has to offer.

Are there vacation rentals with WiFi in Westport?

Westport has 15 vacation rentals with WiFi, so you can stay connected while you're on vacation. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to catching up on social media, these Vrbo homes will keep you online.

Explore destinations around Westport

Compo Beach (255)

Old Mill Beach (288)

Sherwood Island State Park (257)

Alvord Beach (253)

Burying Hill Beach (252)

Sherwood Island State Park (257)

Westport Country Playhouse (706)

Levitt Pavilion (705)

Westport Historical Society (706)

Earthplace Museum (264)

Rental Ideas

Vrbo just got better

Find spaces that suit your style

Find properties near top attractions in Westport

Compo Beach