Book Exclusive Westport Vacation Packages

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Westport flight + hotel packages

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

Westchester Marriott

4.5 out of 5
Price was CA $967, price is now CA $808 per person
CA $808
per person
Dec 13 - Dec 16
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Book a stay at this spa hotel in Tarrytown. Enjoy free parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westchester County Center and Orange Trailhead are located nearby.
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Save 100% on your flight
Price was CA $1,370, price is now CA $921 per person
CA $921
per person
Dec 13 - Dec 16
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Book a stay at this business-friendly apartment in Yonkers. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.
Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

4 out of 5
Save 100% on your flight
Price was CA $1,906, price is now CA $1,464 per person
CA $1,464
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
Book a stay at this business-friendly villa in White Plains. Enjoy free WiFi, free parking, and a garden. Popular attractions Westchester County Center and Jacob Purdy House are located nearby.
Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Downtown Rochelle
Price was CA $1,509, price is now CA $1,325 per person
CA $1,325
per person
Dec 15 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to White Plains (HPN)
Book a stay at this business-friendly hotel in New Rochelle. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New Roc City and Glen Island Park are located nearby.
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
Price was CA $937, price is now CA $828 per person
CA $828
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
Book a stay at this business-friendly hotel in Nyack. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Edward Hopper House Art Center and Buttermilk Falls Park are located nearby.

Top Westport hotels deals

Delamar Westport

Delamar Westport

4 out of 5
1595 Post Rd E Westport CT
The price is CA $224 per night
CA $224
CA $286 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this hotel in Westport. Enjoy free breakfast, free valet parking, and free train station pick-up. Popular attractions Southport Beach and Burying Hill Beach are located nearby.
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave Stamford CT
The price is CA $149 per night
CA $149
CA $171 total
Oct 8 - Oct 9
includes taxes & fees
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Public Library - Ferguson Library are located nearby.
La Quinta Inn & Suites by Wyndham Stamford / New York City

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

3 out of 5
135 Harvard Avenue Stamford CT
Free cancellation
Reserve now, pay when you stay
The price is CA $137 per night
CA $137
CA $158 total
Oct 25 - Oct 26
includes taxes & fees
Stay at this hotel in Stamford. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Mill River Park are located nearby.
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
The price is CA $252 per night
CA $252
CA $289 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Mianus Park are located nearby.
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road Fairfield CT
The price is CA $254 per night
CA $254
CA $306 total
Oct 18 - Oct 19
includes taxes & fees
Book a stay at this beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions South Benson Marina and Fairfield Museum and History Center are located nearby.
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Free cancellation
Reserve now, pay when you stay
The price is CA $160 per night
CA $160
CA $184 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Danbury Fair Mall and Xtreme Play Adventure Park are located nearby.
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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

Westport Vacations

Before you jet off to Westport on a whim, take some time to learn a little about it.

Westport sits 45 miles (72 kilometers) to the northeast of New York, a noteworthy city.

Love meeting the locals while you're on vacation? This part of Connecticut boasts a population of around 26,000 people.

Places to visit in Westport

Sure, singing along to music on your laptop is nice, but nothing beats the feeling of going to a breathtaking live performance! So why not catch an event at Levitt Pavilion? Need some more ideas? The intimacy and accomplishment of theater is difficult to deny. Secure tickets to a show at Westport Country Playhouse and experience the magic for yourself! But there's more. Want to soothe stress of modern life? Breathe in the fresh air as you take off on an adventure through Sherwood Island State Park.

Where do you fly into for Westport?

Prepare for some wonderful adventures in Westport. Once you've headed out of LaGuardia Airport (LGA), the center of town will be 35 miles (56 kilometers) away.

Frequently asked questions

How much are vacation packages to Westport?
Your travel daydreams can become a reality in Westport from as little as CA $808. 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 64 kilometers 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 64 kilometers southwest of downtown Westport. Liberty Intl. Airport (EWR) (88 kilometers away from central Westport) and LaGuardia Airport (LGA) (56 kilometers 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.

Photos of local treasures

Browse Westport vacation photos for more inspiration

A calm river reflecting buildings and trees, with a clear sky above.
A cannon on a stone pedestal by the sea.
A cannon on a stone pedestal by the sea with a person standing in the background.
A beach at sunset with a wooden fence, picnic tables, and people walking.
A person standing on a rocky shoreline with green moss, overlooking a calm sea under a cloudy sky.

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