Westport Vacation Packages 2026 from $578

Westport flight + hotel vacation packages

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

Luxury 1BR located in Prime Yonkers Area

Bryn Mawr

Save 100% on your flight

$578

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Orlando (MCO) to White Plains (HPN)

Luxury 3 BR Near NYC with Easy Parking

Bryn Mawr

Save 100% on your flight

$595

per person

Nov 14 - Nov 17

found 23 hours ago

Roundtrip flight included

Orlando (MCO) to White Plains (HPN)

Free WiFi in public areas is available at this vacation home.

Modern Comfort in the Heart of NYC

Southeast Yonkers

$590

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the laundry service. Laundry facilities and a virtual front desk are also provided.

Modern Luxury Home w GameRoom & Parking

Southeast Yonkers

Save 100% on your flight

$1,394

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

A rooftop terrace, free self parking, and laundry facilities are featured at this vacation home. Dry cleaning is also provided.

Luxury 5 BR Home Free Parking

Bryn Mawr

Save 100% on your flight

$931

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Orlando (MCO) to White Plains (HPN)

This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. Dry cleaning and a virtual front desk are also provided.

Top Westport hotels deals

Delamar Westport

1595 Post Rd E Westport CT

$182 nightly

$206 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and free perks like buffet breakfast and valet parking. Enjoy the sauna and conveniences like a 24-hour front desk and concierge services.

Pool

Breakfast included

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$122 total

Nov 5 - Nov 6

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

$205 total

Oct 25 - Oct 26

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

Trumbull Marriott Shelton

180 Hawley Ln Trumbull CT

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$175 total

Oct 18 - Oct 19

Total with 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 WiFi. You'll appreciate the hot tub, bar/lounge, and laundry facilities.

Pool

Hot Tub

J House Greenwich

1114 E. Putnam Ave Riverside CT

$252 nightly

$290 total

Oct 18 - Oct 19

Total with taxes and fees

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free valet parking. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and free self parking.

Pool

Breakfast included

The Stamford Hotel

700 East Main Street Stamford CT

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$183 total

Nov 4 - Nov 5

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

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.

Stay near popular Westport attractions

Compo Beach

9.6/10 (20 reviews)

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.

See properties

Frequently asked questions

How much are vacation packages to Westport?

Your travel daydreams can become a reality in Westport from as little as $578. 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.