Westport Vacation Packages 2026 from $1,407

Westport flight + hotel vacation packages

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

Luxury NYC Home with Free Parking for 12

$1,407

per person

Nov 24 - Nov 29

found 9 hours ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

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

Luxury NY Home with Free Parking

Save 100% on your flight

$2,975

per person

Nov 24 - Nov 29

found 9 hours ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the onsite laundry facilities and in-room childcare. Dry cleaning and luggage storage are also provided.

Luxury NYC Home Game Room Free Parking

$1,590

per person

Nov 24 - Nov 29

found 9 hours ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, dry cleaning, and laundry facilities are also on offer.

3BR Prime Luxury NY - Free Parking

Save 100% on your flight

$2,284

per person

Nov 24 - Nov 29

found 9 hours ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

Stanton House Inn

$1,799

per person

Nov 24 - Nov 29

found 9 hours ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

A seasonal outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A business center, a coffee shop, and a terrace are also on offer.

Top Westport hotels deals

Delamar Westport

1595 Post Rd E Westport CT

$194 nightly

$220 total

Sep 27 - Sep 28

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

Trumbull Marriott Shelton

180 Hawley Ln Trumbull CT

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$175 total

Sep 20 - Sep 21

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

Hyatt Regency Greenwich

1800 E Putnam Avenue Old Greenwich CT

Free Cancellation

Reserve now, pay when you stay

$180 nightly

$207 total

Sep 27 - Sep 28

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

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

135 Harvard Avenue Stamford CT

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$107 total

Sep 28 - Sep 29

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. 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.

Breakfast included

Pet friendly

Ethan Allen Hotel

21 Lake Avenue Extension Danbury CT

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$126 total

Sep 27 - Sep 28

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, free WiFi in public areas, and free train station pick-up. Enjoy the seasonal outdoor pool and perks like free self parking.

Pool

Pet friendly

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

$89 nightly

$103 total

Sep 28 - Sep 29

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

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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 $1,407. 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.