Westport Vacation Packages 2026 from $764

Westport flight + hotel vacation packages

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

Red Carpet Inn

Cove - East Side - Shippan

$764

per person

Jul 20 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to White Plains (HPN)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. The front desk is staffed around-the-clock and laundry facilities are on offer.

The Armon Stamford Hotel & Conference

Ridgeway-Bullshead

$803

per person

Jul 20 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to White Plains (HPN)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 17 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and free buffet breakfast.

The Stamford Hotel

Downtown Stamford

$850

per person

Jul 20 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to White Plains (HPN)

This hotel features a 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 snack bar/deli are also offered.

3BR Prime Luxury near NYC w Arcade Room

Southeast Yonkers

Save 100% on your flight

$2,111

per person

Jun 26 - Jun 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to White Plains (HPN)

This vacation home features free WiFi in public areas, dry cleaning, and a virtual front desk.

SpringHill Suites by Marriott Tarrytown Westchester County

$927

per person

Jul 20 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to White Plains (HPN)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Top Westport hotels deals

Delamar Westport

1595 Post Rd E Westport CT

$257 nightly

$296 total

May 20 - May 21

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.

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.

Hyatt Regency Greenwich

1800 E Putnam Avenue Old Greenwich CT

$212 nightly

$243 total

Apr 25 - Apr 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.

EVEN Hotel Norwalk by IHG

426 Main Ave, Route 7 Norwalk CT

Free Cancellation

$118 nightly

$136 total

May 25 - May 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.

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$119 total

Apr 27 - Apr 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.

Trumbull Marriott Shelton

180 Hawley Ln Trumbull CT

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$171 total

Apr 26 - Apr 27

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.

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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 $764. 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.