Westport Vacations 2025/2026 from CA $601

Westport flight + hotel packages

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

EVEN Hotel Norwalk by IHG

per person

Oct 8 - Oct 11

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.

Hilton Stamford Hotel & Executive Meeting Center

Waterside

per person

Oct 8 - Oct 11

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 Stamford. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mill River Park and Stamford Center for the Arts are located nearby.

The Lloyd Stamford, Tapestry Collection by Hilton

Downtown Stamford

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to White Plains (HPN)

Stay at this 3.5-star boutique hotel in Stamford. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mill River Park and Stamford Center for the Arts are located nearby.

The Stamford Hotel

Downtown Stamford

per person

Oct 8 - Oct 11

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 Stamford. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stamford Town Center and Stamford Center for the Arts are located nearby.

Hampton Inn White Plains/Tarrytown

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to White Plains (HPN)

Stay at this 3-star business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westchester County Center and Westchester Broadway Theatre are located nearby.

Top Westport hotels deals

Inn at Longshore

260 Compo Rd S, Westport, CT

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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

Norwalk Inn & Conference Center

99 East Avenue, Norwalk, CT

Free cancellation

Reserve now, pay when you stay

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Stay at this 4-star hotel in Norwalk. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the bar in our reviews. Popular attractions Norwalk Islands and Stepping Stones Museum for Children are located nearby.

Pool

Parking included

Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

Free cancellation

Reserve now, pay when you stay

Get rates

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 Stamford Center for the Arts are located nearby.

Breakfast included

Parking included

La Quinta Inn & Suites by Wyndham Stamford / New York City

135 Harvard Avenue, Stamford, CT

Free cancellation

Reserve now, pay when you stay

CA $115

CA $132 total

Aug 11 - Aug 12

includes taxes & fees

Stay at this 3-star business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Mill River Park are located nearby.

Pool

Breakfast included

Hyatt Regency Greenwich

1800 E Putnam Avenue, Old Greenwich, CT

Free cancellation

Reserve now, pay when you stay

CA $241

CA $277 total

Aug 31 - Sep 1

includes taxes & fees

Book a stay at this eco-certified hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Mill River Park are located nearby.

Pool

Pet-friendly

Trumbull Marriott Shelton

180 Hawley Ln, Trumbull, CT

Free cancellation

Reserve now, pay when you stay

CA $186

CA $214 total

Aug 24 - Aug 25

includes taxes & fees

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.

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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 $601. 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.