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Westport flight + hotel packages

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Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
per person
Aug. 3 - Aug. 7
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Stay at this 3-star 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.
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Jun. 18 - Jun. 22
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
Book a stay at this business-friendly vacation home in Yonkers. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Bronx Zoo and Yonkers Raceway are located nearby.
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Jun. 18 - Jun. 22
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
Stay at this 3-star vacation home in Yonkers. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Bronx Zoo and Yankee Stadium are located nearby.
Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Jun. 18 - Jun. 22
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
Stay at this 4-star vacation home in Yonkers. Enjoy free WiFi, laundry facilities, and a picnic area. Popular attractions Bronx Zoo and George Washington Bridge are located nearby.
The Armon Hotel & Conference

The Armon Hotel & Conference

2 out of 5
per person
Jul. 14 - Jul. 17
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Stay at this 3-star business-friendly hotel in Stamford. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the clean rooms in our reviews. Popular attractions Hand & Stone Massage and Facial Spa and First Presbyterian Church are located nearby.

Top Westport hotels deals

Inn at Longshore

Inn at Longshore

2.5 out of 5
260 Compo Rd S, Westport, CT
The price is CA $297 per night
CA $297
per night
May 12 - May 13
Book a stay at this golf hotel in Westport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Compo Beach and Old Mill Beach are located nearby.
Pet-friendly
Breakfast included
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $137 per night
CA $137
per night
May 19 - May 20
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stamford Town Center and Fernando Luis Alvarez Gallery are located nearby.
Pet-friendly
Breakfast included
EVEN Hotel Norwalk, an IHG Hotel

EVEN Hotel Norwalk, an IHG Hotel

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $162 per night
CA $162
per night
Jun. 10 - Jun. 11
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Caldor Shopping Center and Gateway Shopping Center are located nearby.
Pet-friendly
Parking included
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd, Shelton, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $150 per night
CA $150
per night
May 23 - May 24
Stay at this 3-star business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SportsCenter of Connecticut and Roosevelt Forest are located nearby.
Pet-friendly
Pool
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $127 per night
CA $127
per night
May 14 - May 15
Stay at this 3-star beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Hartford HealthCare Amphitheater and South Benson Marina are located nearby.
Pet-friendly
Pool
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
Free cancellation
The price is CA $257 per night
CA $257
per night
May 27 - May 28
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Museum of Black World War II History are located nearby.
Pet-friendly
Pool
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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

Image for Compo Beach

Compo Beach

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.

Compo Beach
Image for Levitt Pavilion

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.

Levitt Pavilion
Image for Westport Country Playhouse

Westport Country Playhouse

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.

Westport Country Playhouse

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?
Vacation packages, which include hotels and flights in Westport, start from just CA $585. Make your travel dreams a reality and secure your trip with Travelocity today.
How long should my Westport vacation be?
Most sightseers stay in Westport for around 2 nights. That said, traveling is all about discovering new things and creating memories — why not book a few additional nights so you can do just that?
Where can I get the best vacation package deals for Westport?
Grabbing the best package deal to Westport is a cinch with Travelocity. With as many as 400 partner airlines and 665,000 properties all over the globe, you won’t be short of choice when selecting your hotels and flights.
Why should I book my Westport vacation package with Travelocity?
From enticing destinations to memorable experiences, we have everything you need to appease your wanderlust. Our 24/7 customer support will also ensure you’re taken care of during your vacation. And don’t panic if you spot a lower price on your reservation, we’ll match it. That’s our Price Match Guarantee.
Will I save money on my Westport car rental if I book it with hotels and flights?
With a Westport vacation package, you can bundle your car, hotel and flight bookings and save a whole lot. If you’re in the mood to explore the best of this awesome area, why not start with Broadway? This renowned attraction is 69 kilometersfrom Westport. With your own set of wheels, you’ll be there in a jiffy.
What is the best time of year to go to Westport?
Take your vacation in and spend more money on memorable experiences, rather than your hotel. This is the most affordable month to lock in a stay. Prices are highest in , so avoid traveling then if your budget is smaller. is the busiest period for Westport. You’ll need to book well in advance and be prepared to pay premium prices. are the least popular months to visit.
Which airport is best for Westport?
New York, NY (JFK-John F. Kennedy Intl.) (64 kilometersaway from the downtown area), Newark, NJ (EWR-Liberty Intl.) (85 kilometersaway from central Westport) and New York, NY (LGA-LaGuardia) (60 kilometersaway from central Westport) are the top options for Westport.
What is there to do in Westport?
Don’t miss the fantastic photo opportunities at Westport Country Playhouse, one of the most renowned attractions in Westport. There’s plenty more to discover in this great destination, so give yourself enough time to see some of its off-the-beaten-path gems.
Where should I stay when visiting Westport?
Many travelers choose to stay at The Westport Inn. It’s the perfect base for your Westport getaway.
Can I go on vacation to Westport at this time?
Discover all the info that’s important relating to quarantine policies and travel restrictions before you fly to Westport. Our Covid-19 Travel Advisor is full of advice to help make your vacation as hassle-free as possible.