Westport Vacation Packages 2026 from $266

Westport flight + hotel vacation packages

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

Courtyard by Marriott Poughkeepsie

$266

per person

Mar 7 - Mar 11

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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. Self parking, a coffee shop, and a terrace are also offered.

Hampton Inn & Suites Yonkers

Northwest Yonkers

$415

per person

Apr 15 - Apr 19

found 16 hours ago

Roundtrip flight included

Dallas (DFW) to White Plains (HPN)

This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Courtyard by Marriott Yonkers Westchester County

Northwest Yonkers

$310

per person

Feb 28 - Mar 4

found 1 day ago

Roundtrip flight included

Dallas (DFW) to White Plains (HPN)

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

The Thayer Hotel at West Point

$455

per person

Mar 31 - Apr 4

found 2 hours ago

Roundtrip flight included

Dallas (DFW) to White Plains (HPN)

Free WiFi in public areas, a terrace, and a computer station are available at this hotel. Traveling on business? Take advantage of the 6 onsite conference rooms. Luggage storage and wedding services are also provided.

Stamford Suites

Downtown Stamford

$371

per person

Mar 14 - Mar 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) to White Plains (HPN)

This aparthotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-in. Express check-out, dry cleaning, and luggage storage are also on offer.

Top Westport hotels deals

Delamar Westport

1595 Post Rd E Westport CT

$186 nightly

$214 total

Jan 25 - Jan 26

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and valet parking. You'll appreciate the free shopping center shuttle, free self parking, and free WiFi in public areas.

Pool

Breakfast included

EVEN Hotel Norwalk by IHG

426 Main Ave, Route 7 Norwalk CT

Free Cancellation

$122 nightly

$140 total

Jan 25 - Jan 26

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

$146 nightly

$167 total

Jan 29 - Jan 30

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

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$119 total

Jan 27 - Jan 28

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

Motel 6 Milford, CT

111 Schoolhouse Road Milford CT

Free Cancellation

Reserve now, pay when you stay

$55 nightly

$64 total

Feb 8 - Feb 9

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. A snack bar/deli, express check-out, and laundry facilities are also on offer.

Pet friendly

Parking included

Hyatt Place Milford / New Haven

190 Old Gate Lane Milford CT

Free Cancellation

Reserve now, pay when you stay

$91 nightly

$105 total

Jan 28 - Jan 29

Total with taxes and fees

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. Guests will appreciate freebies like buffet breakfast and free self parking.

Breakfast included

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

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 $266. 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.