Westport Vacation Packages 2026 from $819

Westport flight + hotel vacation packages

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

Tarrytown House Estate

Save 100% on your flight

$819

per person

Sep 20 - Sep 26

found 21 hours ago

Roundtrip non-stop flight included

Orlando (MCO) 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.

Luxury 3BR Family Home Game Room Parking

Bryn Mawr

Save 100% on your flight

$1,048

per person

Sep 20 - Sep 26

found 21 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to White Plains (HPN)

This apartment features a virtual front desk. Take advantage of the free self parking.

Modern Luxury Home w GameRoom & Parking

Southeast Yonkers

Save 100% on your flight

$3,621

per person

Sep 20 - Sep 26

found 21 hours ago

Roundtrip non-stop flight included

Orlando (MCO) 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 NY Home with Free Parking

Save 100% on your flight

$3,218

per person

Sep 20 - Sep 26

found 21 hours ago

Roundtrip non-stop flight included

Orlando (MCO) 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.

Upscale Modern Luxury 3BR Home

Save 100% on your flight

$1,460

per person

Sep 20 - Sep 26

found 21 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to White Plains (HPN)

Top Westport hotels deals

Delamar Westport

1595 Post Rd E Westport CT

$265 nightly

$305 total

Jul 5 - Jul 6

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.

Hyatt Regency Greenwich

1800 E Putnam Avenue Old Greenwich CT

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$216 total

Jul 26 - Jul 27

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

$95 nightly

$109 total

Jul 26 - Jul 27

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

$106 nightly

$122 total

Jul 19 - Jul 20

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.

EVEN Hotel Norwalk by IHG

426 Main Ave, Route 7 Norwalk CT

Free Cancellation

$135 nightly

$155 total

Jul 5 - Jul 6

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

Hilton Garden Inn Milford

291 Old Gate Lane Milford CT

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$132 total

Jul 12 - Jul 13

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.

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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

A calm lake with houses along the shore and autumn-colored trees in the background.

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 $819. 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.