Westport Vacation Packages 2026 from $567

Westport flight + hotel vacation packages

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

Delamar Southport

$567

per person

Jun 12 - Jun 14

found 18 hours ago

Roundtrip flight included

Tampa (TPA) 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.

Luxury Living in the Heart of NY

Southeast Yonkers

Save 100% on your flight

$2,739

per person

May 21 - May 25

found 1 day ago

Roundtrip flight included

San Juan (SJU) to White Plains (HPN)

This vacation home features free WiFi in public areas, a picnic area, and laundry facilities. Barbecue grills are provided for your convenience.

Cromwell Manor Inn

$693

per person

May 26 - May 29

found 1 day ago

Roundtrip flight included

Dallas (DFW) to White Plains (HPN)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free cooked-to-order breakfast each morning. Dry cleaning, luggage storage, and wedding services are also on offer.

Luxury NY Home 3BR with Easy Parking

Southeast Yonkers

Save 100% on your flight

$2,195

per person

May 21 - May 25

found 1 day ago

Roundtrip flight included

San Juan (SJU) to White Plains (HPN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the laundry service.

Modern Comfort in the Heart of NYC

Southeast Yonkers

$1,063

per person

May 21 - May 25

found 1 day ago

Roundtrip flight included

San Juan (SJU) 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.

Top Westport hotels deals

Delamar Westport

1595 Post Rd E Westport CT

$201 nightly

$231 total

Apr 8 - Apr 9

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

Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.

Westport CT

Get rates

This vacation home features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.

Pool

Hot Tub

Hyatt Place Milford / New Haven

190 Old Gate Lane Milford CT

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$116 total

Apr 5 - Apr 6

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

Motel 6 Milford, CT

111 Schoolhouse Road Milford CT

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$75 total

Apr 5 - Apr 6

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

Trumbull Marriott Shelton

180 Hawley Ln Trumbull CT

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$146 total

Mar 29 - Mar 30

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

Best Western Danbury/Bethel

11 Stony Hill Road Bethel CT

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$86 total

Apr 5 - Apr 6

Total with taxes and fees

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 2 conference rooms, along with the business center. Multilingual staff can provide around-the-clock assistance and free newspapers are on offer.

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.

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.

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

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.

Frequently asked questions

How much are vacation packages to Westport?

Your travel daydreams can become a reality in Westport from as little as $567. 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.