Westport Vacations 2024/2025 from CA $1,064

Westport flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Delamar Greenwich Harbor

per person

Jan. 1 - Jan. 5

found 7 hours ago

Roundtrip flight included

Buffalo (BUF) to White Plains (HPN)

Book a stay at this beach hotel in Greenwich. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenwich Ferry Dock and Bruce Museum of Arts and Science are located nearby.

The Abbey Inn & Spa

Save 100% on your flight

per person

Dec. 26 - Jan. 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to White Plains (HPN)

Stay at this 4-star spa hotel in Peekskill. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and Dramatic Hall are located nearby.

Hyatt Regency Greenwich

Save 100% on your flight

per person

Dec. 26 - Jan. 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to White Plains (HPN)

Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Museum of Black World War II History are located nearby.

Tarrytown House Estate on the Hudson

per person

Dec. 22 - Dec. 25

found 2 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to White Plains (HPN)

Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Lyndhurst Mansion and Washington Irving's Sunnyside are located nearby.

Top Westport hotels deals

Inn at Longshore

260 Compo Rd S, Westport, CT

CA $222

CA $256 total

includes taxes & fees

24 Nov - 25 Nov

Book a stay at this golf hotel in Westport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Compo Beach and Old Mill Beach are located nearby.

Westport Paradise With Every Amenity!

CA $684

CA $989 total

includes taxes & fees

23 Nov - 24 Nov

Stay at this apartment in Westport. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Westport Country Playhouse and Westport Historical Society are located nearby.

Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

Free cancellation

Reserve now, pay when you stay

CA $140

CA $162 total

includes taxes & fees

30 Nov - 1 Dec

Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stamford Town Center and Fernando Luis Alvarez Gallery are located nearby.

The Circle Hotel Fairfield

417 Post Road, Fairfield, CT

Free cancellation

Reserve now, pay when you stay

CA $189

CA $217 total

includes taxes & fees

1 Dec - 2 Dec

Stay at this 3-star beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions South Benson Marina and Fairfield Museum and History Center are located nearby.

Trumbull Marriott Shelton

180 Hawley Ln, Trumbull, CT

Free cancellation

Reserve now, pay when you stay

CA $177

CA $204 total

includes taxes & fees

8 Dec - 9 Dec

Stay at this hotel in Trumbull. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Roosevelt Forest and Boothe Memorial Park and Museum are located nearby.

Norwalk Inn & Conference Center

99 East Avenue, Norwalk, CT

Free cancellation

Reserve now, pay when you stay

CA $187

CA $216 total

includes taxes & fees

24 Nov - 25 Nov

Stay at this hotel in Norwalk. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in our reviews. Popular attractions Norwalk Islands and Stepping Stones Museum for Children are located nearby.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Compo Beach

Why not spend a carefree afternoon at Compo Beach during your travels in Westport? Stroll along the seaside or experience the area's art scene.

Westport Country Playhouse

You can get tickets for a performance at Westport Country Playhouse during your stay in Westport. While you're in the area, stroll along the beautiful beaches.

Westport Farmers Market

You can browse for the perfect souvenirs at Westport Farmers Market during your visit to Westport. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Westport Vacations

Before you jet off to Westport on a whim, take some time to learn a little about it.

Westport sits 45 miles (72 kilometers) to the northeast of New York, a noteworthy city.

Love meeting the locals while you're on vacation? This part of Connecticut boasts a population of around 26,000 people.

Places to visit in Westport

Sure, singing along to music on your laptop is nice, but nothing beats the feeling of going to a breathtaking live performance! So why not catch an event at Levitt Pavilion? Need some more ideas? The intimacy and accomplishment of theater is difficult to deny. Secure tickets to a show at Westport Country Playhouse and experience the magic for yourself! But there's more. Want to soothe stress of modern life? Breathe in the fresh air as you take off on an adventure through Sherwood Island State Park.

Where do you fly into for Westport?

Prepare for some wonderful adventures in Westport. Once you've headed out of LaGuardia Airport (LGA), the center of town will be 35 miles (56 kilometers) away.

Frequently asked questions

How much are vacation packages to Westport?

Your travel daydreams can become a reality in Westport from as little as CA $1,064. Packages include flights and hotels, so organizing everything should be a cinch. All you’ll have to concentrate on is having a good time.

How long should my Westport vacation be?

Typically, 2 nights is how long most travelers spend exploring the attractions of Westport. Wondering if you’ll have sufficient time to cross everything off your travel itinerary? Stay a couple more nights and experience everything this place has to offer.

Where can I get the best vacation package deals for Westport?

It’s simple — look no further than Travelocity. With no less than 400 air carriers and 1,000,000 properties across the globe, it’s a piece of cake to find a Westport package deal that ticks all your boxes.

Why should I book my Westport vacation package via Travelocity?

We make traveling the world easy. Whether you’re after an amazing new place to uncover or want to ensure you get the best deal around, we’re here to assist. Our 24/7 customer support, excellent service and Price Match Guarantee mean you can book with confidence.

Can I save on my Westport car rental if I bundle it with a hotel or flight?

Sure can — bundle your car, flight and hotel into a Westport vacation package and you’ll save a tidy sum. With so much to discover in the Westport area, having your own set of wheels will make exploring a joy. Once you’re in the driver’s seat, crank up the tunes and head toward Times Square, a famous sight roughly 64 kilometers from Westport.

Which airport is best for Westport?

It’s highly likely you’ll be landing at John F. Kennedy Intl. Airport (JFK), which is 64 kilometers southwest of downtown Westport. Liberty Intl. Airport (EWR) (88 kilometers away from central Westport) and LaGuardia Airport (LGA) (56 kilometers away from central Westport) are other options.

What is there to do in Westport?

There is a certain magic as you wander the streets of Westport. Compo Beach and Levitt Pavilion are just a couple of highlights that entice visitors to this wonderful city, so add them to your travel itinerary.

Where should I stay when visiting Westport?

If you’re after somewhere to base yourself, check out the The Westport Inn, an Ascend Collection Hotel. It’s the top pick for many travelers.