Westport Vacation Rentals, Connecticut: house rentals & more

Discover a selection of 51 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.

Vacation rentals with weekly discounts - Westport

Showing deals for:Aug 1 - Aug 8

Exceptional

(28 reviews)

Cozy country cottage in horse country ,private 1 hour toNYC

South Salem, NY

10% off

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Westport

Compo Beach

Find the best place to stay - Westport

Your perfect Westport getaway is here!

Sleeps 4 · 2 bedrooms · 1 bathroom

Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.

Sleeps 9 · 3 bedrooms · 2 bathrooms

Come to your summer home-mile to Saugatuck/Compo-bright, open, airy, fenced yard

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Top rated rentals - Westport

The Frida Kahlo Room. Spacious, cheerful, with a Smart TV and nook.

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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?

Cottages are the most popular kind of vacation rental in Westport, according to our data. Even if you have a different idea about what you want, Vrbo has properties in many shapes and sizes. Filter our options to find your ideal match.

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

A range of factors can affect how much you pay for a vacation rental in Westport, like the time of year, length of stay and property type. Still, all of our vacation homes have something in common — incredible value. Simply add your travel dates to find your dream escape.

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

When you travel and the style and size of the property will influence the cost of your beachside stay. Put in your Westport travel dates to view your options on Vrbo. Can’t live without a hot tub, or maybe a private pool? Use the filters to select the amenities and features you want in your beach house.

Are there pet-friendly vacation rentals in Westport?

Pack a tug toy and treats for your puppy dog because Westport has 50 vacation rentals that roll out the welcome mat to pets. Let your furriest friend join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check the “Pets allowed” filter box.

Can I rent a house with a pool in Westport?

Add a whole new level of fun to your vacation by booking one of the 21 houses with a private pool in Westport. Use our search filter to find properties with pools on Vrbo, then spend leisurely days playing and splashing in a swimming pool that’s only for you.

What are popular rental amenities in Westport?

Some of the most popular rental amenities people prefer in Westport are an electric car charging station, a fireplace and a beach view. Whether you’re on a trip with pals, family or even pets, Vrbo vacation rentals have the best amenities for chilling out with the people you love.

Are there large group vacation rentals in Westport?

You can choose from 14 vacation rentals in Westport that can sleep 10 or more guests. Whether you’re organizing a family vacation or an event like an anniversary, there’s plenty of room to get your loved ones together under one roof.

Are there vacation rentals in Westport that welcome kids?

Gather your whole crew for a fun-packed adventure in Westport at one of our 48 family-friendly vacation properties. Lots of these stays feature amenities that are ideal for getaways with the kids, such as dining rooms, living rooms and swimming pools. Just check the “Properties good for families” filter box and book your favorite.

What are the top attractions for families in Westport?

Keeping the kids happy during your Westport vacation is simple with these family-friendly attractions:

Compo Beach
Levitt Pavilion
Westport Country Playhouse

Are there one-bedroom vacation rentals in Westport?

Yes, you can take your pick from six one-bedroom rentals in Westport. Whether you’d prefer an apartment or a cabin, Vrbo’s one-bedroom rentals are ideal if you don’t require a huge amount of space. One of the major perks of having your own pad? You won’t ever have to share your trip with strangers.

Can I find two-bedroom vacation rentals in Westport?

Gather your family and relax in total privacy and comfort in one of the two two-bedroom vacation properties Westport has to offer.

Are there vacation rentals with WiFi in Westport?

Take your pick of 18 vacation rentals with WiFi in Westport. If you’d like to disconnect from the world during your break, but still want to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Westport?

Westport has 47 vacation rentals where you can kick back in air-conditioned comfort. To book a property on Vrbo offering this amenity, enter your dates of travel and use the filter tool to select the “air conditioning” box.

How old do you have to be to rent a vacation rental in Westport?

We advise checking with the Westport vacation rental you’d like on Vrbo as age restrictions differ. However, it’s generally 16, 18 or 21.

How long can I rent a vacation rental in Westport for?

It all depends on the Westport property. To see all available options offering extended stays, simply type your travel dates and number of people into Vrbo’s search page. You can look forward to having the whole property to yourself, as well as comforts such as air conditioning, a kitchen and a backyard where the kids can run around and play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

Does Vrbo offer discounts for vacation homes in Westport?

Overnight trip or extended vacation, Vrbo has some fantastic deals and discounts in Westport that’ll suit your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what’s just been added with one of our newly listed homes. Whatever you’re after, you’ll find the perfect place to stay — without breaking the bank.