Westport Vacation Packages 2025/2026 from $308

Westport flight + hotel vacation packages

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

Hilltop Inn & Suites

Northwest Yonkers

Save 100% on your flight

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Detroit (DTW) to White Plains (HPN)

A gym is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A computer station is provided and the front desk is staffed around-the-clock.

Tarrytown House Estate

Save 100% on your flight

per person

Sep 17 - Sep 20

found 23 hours ago

Roundtrip flight included

Detroit (DTW) to White Plains (HPN)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the gym and perks like free self parking.

Royal Regency Hotel

Northwest Yonkers

Save 100% on your flight

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Detroit (DTW) to White Plains (HPN)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and onsite conference space. Enjoy the gym and conveniences like a 24-hour front desk and wedding services.

The Stamford Hotel

Downtown Stamford

per person

Oct 31 - Nov 2

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to White Plains (HPN)

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

Delamar Southport

per person

Oct 31 - Nov 2

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to White Plains (HPN)

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Top Westport hotels deals

Inn at Longshore

260 Compo Rd S, Westport, CT

$217 nightly

$249 total

Aug 26 - Aug 27

Total includes 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 laundry service. A garden, a snack bar/deli, and a picnic area are also on offer.

Norwalk Inn & Conference Center

99 East Avenue, Norwalk, CT

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$141 total

Aug 17 - Aug 18

Total includes taxes and fees

This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a poolside bar on site, and laundry facilities and concierge services are also provided.

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

135 Harvard Avenue, Stamford, CT

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$104 total

Sep 7 - Sep 8

Total includes taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

$100 nightly

$116 total

Aug 14 - Aug 15

Total includes 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.

Hyatt Regency Greenwich

1800 E Putnam Avenue, Old Greenwich, CT

$175 nightly

$201 total

Aug 31 - Sep 1

Total includes 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. Self parking, a coffee shop, and a snack bar/deli are also offered.

Trumbull Marriott Shelton

180 Hawley Ln, Trumbull, CT

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$155 total

Aug 24 - Aug 25

Total includes taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and laundry facilities.

Don't see what you're looking for?

See all available properties in Westport

View all properties

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.

Frequently asked questions

How much are vacation packages to Westport?

Your travel daydreams can become a reality in Westport from as little as $308. 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.