Westport Vacation Packages 2026/2026 from $277

Westport flight + hotel vacation packages

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

Hotel NoMa, Trademark Collection by Wyndham

Save 100% on your flight

$277

per person

Jan 18 - Jan 22

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

A nightclub and an outdoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Courtyard by Marriott Poughkeepsie

Save 100% on your flight

$351

per person

Feb 12 - Feb 18

found 7 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to White Plains (HPN)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a coffee shop, and a terrace are also offered.

Spacious 3BR Luxe Escape near NYC

Southeast Yonkers

Save 100% on your flight

$759

per person

Jan 13 - Jan 18

found 19 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to White Plains (HPN)

Hampton Inn White Plains/Tarrytown

$445

per person

Feb 17 - Feb 22

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to White Plains (HPN)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the express check-in and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

The Armon Stamford Hotel & Conference

Ridgeway-Bullshead

$431

per person

Jan 11 - Jan 15

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to White Plains (HPN)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 17 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and free buffet breakfast.

Top Westport hotels deals

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$119 total

Dec 10 - Dec 11

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a terrace are also provided.

Breakfast included

Parking included

Hyatt Regency Greenwich

1800 E Putnam Avenue Old Greenwich CT

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$204 total

Dec 21 - Dec 22

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. There's a bar/lounge on site, and concierge services and wedding services are also provided.

Pool

Pet friendly

Norwalk Inn & Conference Center

99 East Avenue Norwalk CT

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$160 total

Dec 14 - Dec 15

Total with taxes and fees

This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, limo/town car service, and a garden are also on offer.

Parking included

Free WiFi

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

135 Harvard Avenue Stamford CT

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$100 total

Dec 29 - Dec 30

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, express check-in, and express check-out are also offered.

Pool

Breakfast included

EVEN Hotel Norwalk by IHG

426 Main Ave, Route 7 Norwalk CT

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$127 total

Dec 14 - Dec 15

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Pet friendly

Parking included

DoubleTree by Hilton Stamford

1 First Stamford Pl Stamford CT

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$155 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel features an indoor pool, an outdoor tennis court, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the 24-hour gym, bar/lounge, and convenience store.

Pool

Pet friendly

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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

5/5(1 review)

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

5/5(3 reviews)

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.

Frequently asked questions

How much are vacation packages to Westport?

Your travel daydreams can become a reality in Westport from as little as $277. 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 40 mi 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 40 mi southwest of downtown Westport. Liberty Intl. Airport (EWR) (55 mi away from central Westport) and LaGuardia Airport (LGA) (35 mi 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.