Westport Vacations 2025 from CA $734

Westport flight + hotel packages

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

Hilton Stamford Hotel & Executive Meeting Center

Waterside

per person

May 16 - May 19

found 20 hours ago

Roundtrip non-stop flight included

Montreal (YUL) 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.

Cambria Hotel White Plains - Downtown

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

Stay at this 3.5-star business-friendly hotel in White Plains. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions The Westchester Mall and Galleria at White Plains are located nearby.

Hampton Inn & Suites Yonkers

Northwest Yonkers

per person

Apr. 17 - Apr. 22

found 14 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) 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.

Westchester Marriott

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

Stay at this 4.5-star spa hotel in Tarrytown. Enjoy free parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westchester County Center and Captain Lawrence Brewing Company are located nearby.

Hampton Inn & Suites Yonkers - Westchester

Northeast Yonkers

per person

May 16 - May 19

found 10 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to White Plains (HPN)

Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westchester's Ridge Hill and Legoland Discovery Center Westchester are located nearby.

Top Westport hotels deals

EVEN Hotel Norwalk, an IHG Hotel

426 Main Ave, Route 7, Norwalk, CT

Free cancellation

CA $181

CA $208 total

includes taxes & fees

6 Mar - 7 Mar

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.

Pet-friendly

Parking included

Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

Free cancellation

Reserve now, pay when you stay

CA $145

CA $168 total

includes taxes & fees

4 Mar - 5 Mar

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.

Breakfast included

Parking included

Hyatt Regency Greenwich

1800 E Putnam Avenue, Old Greenwich, CT

Free cancellation

Reserve now, pay when you stay

CA $253

CA $291 total

includes taxes & fees

21 Mar - 22 Mar

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.

Pool

Pet-friendly

Hyatt House Shelton

830 Bridgeport Ave, Shelton, CT

Free cancellation

Reserve now, pay when you stay

CA $159

CA $183 total

includes taxes & fees

9 Mar - 10 Mar

Stay at this 3-star business-friendly hotel in Shelton. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SportsCenter of Connecticut and Great River Golf Club are located nearby.

Hot tub

Breakfast included

Hyatt Place Milford / New Haven

190 Old Gate Lane, Milford, CT

Free cancellation

Reserve now, pay when you stay

CA $143

CA $165 total

includes taxes & fees

9 Mar - 10 Mar

Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Milford Plaza Shopping Center are located nearby.

Hot tub

Breakfast included

The Watershed - Formerly Hotel Zero Degrees

353 Main Ave, Norwalk, CT

Free cancellation

Reserve now, pay when you stay

CA $244

CA $281 total

includes taxes & fees

9 Mar - 10 Mar

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

Pet-friendly

Parking included

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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.

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 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 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 $734. 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.