Westport Vacations 2025 from CA $652

Westport flight + hotel packages

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

Hilton Stamford Hotel & Executive Meeting Center

Waterside

per person

Feb. 7 - Feb. 10

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to White Plains (HPN)

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

Hampton Inn & Suites Yonkers

Northwest Yonkers

per person

Mar. 19 - Mar. 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to White Plains (HPN)

Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Untermyer Gardens Conservancy and Legoland Discovery Center Westchester are located nearby.

EVEN Hotel Norwalk, an IHG Hotel

per person

Mar. 19 - Mar. 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to White Plains (HPN)

Stay at this 3.5-star business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Caldor Shopping Center and Silvermine Arts Center are located nearby.

Best Western Fishkill Inn & Suites

per person

Mar. 19 - Mar. 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to White Plains (HPN)

Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Van Wyck Homestead Museum and Blodgett Memorial Library are located nearby.

Modern Luxury Home w GameRoom & Parking

Southeast Yonkers

Save 100% on your flight

per person

Mar. 19 - Mar. 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to White Plains (HPN)

Stay at this 3-star vacation home in Yonkers. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.

Top Westport hotels deals

Inn at Longshore

260 Compo Rd S, Westport, CT

Get rates

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.

Breakfast included

Pet-friendly

Westport Paradise With Every Amenity!

CA $706

CA $1,027 total

includes taxes & fees

13 Jan - 14 Jan 2025

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

Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

Free cancellation

Reserve now, pay when you stay

CA $144

CA $166 total

includes taxes & fees

1 Jan - 2 Jan 2025

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.

EVEN Hotel Norwalk, an IHG Hotel

426 Main Ave, Route 7, Norwalk, CT

Free cancellation

Reserve now, pay when you stay

CA $147

CA $169 total

includes taxes & fees

26 Jan - 27 Jan 2025

Stay at this 3.5-star business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Caldor Shopping Center and Silvermine Arts Center are located nearby.

Hyatt Regency Greenwich

1800 E Putnam Avenue, Old Greenwich, CT

Free cancellation

Reserve now, pay when you stay

CA $292

CA $335 total

includes taxes & fees

24 Jan - 25 Jan 2025

Book a stay at this eco-certified 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.

Hilton Stamford Hotel & Executive Meeting Center

1 First Stamford Pl, Stamford, CT

Free cancellation

Reserve now, pay when you stay

CA $217

CA $250 total

includes taxes & fees

2 Jan - 3 Jan 2025

Book a stay at this business-friendly hotel in Stamford. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Museum of Black World War II History and Stamford Center for the Arts 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.

Levitt Pavilion

You can make plans for a show at Levitt Pavilion during your stay in Westport. While you're in the area, stroll along the beautiful beaches.

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 $652. 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.