Book Exclusive Westport Vacation Packages

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Westport flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
Ridgeway-Bullshead
Price was CA $1,045, price is now CA $884 per person
CA $884
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to White Plains (HPN)
Book a stay at this business-friendly hotel in Stamford. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hand & Stone Massage and Facial Spa and E. Gaynor Brennan Golf Course are located nearby.
Stamford Marriott

Stamford Marriott

3.5 out of 5
Downtown Stamford
Price was CA $1,629, price is now CA $1,349 per person
CA $1,349
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
Book a stay at this spa hotel in Stamford. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Center for the Arts are located nearby.
Hyatus Luxury Residences Stamford

Hyatus Luxury Residences Stamford

4.5 out of 5
Downtown Stamford
Price was CA $1,363, price is now CA $1,154 per person
CA $1,154
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Book a stay at this luxury aparthotel in Stamford. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Stamford Public Library - Ferguson Library and Stamford Town Center are located nearby.
Delamar Southport

Delamar Southport

4 out of 5
Price was CA $1,148, price is now CA $988 per person
CA $988
per person
Dec 20 - Dec 23
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Book a stay at this spa hotel in Southport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Sasco Hill Beach and Southport Beach are located nearby.
Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was CA $1,575, price is now CA $1,356 per person
CA $1,356
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Book a stay at this beach hotel in Greenwich. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Capitol Theatre and Greenwich Ferry Dock 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 $299 per night
CA $299
CA $372 total
Nov 29 - Nov 30
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.
Pool
Breakfast included
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Free cancellation
Reserve now, pay when you stay
The price is CA $290 per night
CA $290
CA $333 total
Nov 22 - Nov 23
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 Capitol Theatre and E. Gaynor Brennan Golf Course are located nearby.
Pool
Pet-friendly
The Stamford Hotel

The Stamford Hotel

3.5 out of 5
700 East Main Street Stamford CT
Free cancellation
Reserve now, pay when you stay
The price is CA $229 per night
CA $229
CA $264 total
Nov 22 - Nov 23
includes taxes & fees
Book a stay at this business-friendly hotel in Stamford. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stamford Town Center and Stamford Public Library - Ferguson Library are located nearby.
Pool
Pet-friendly
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
2701 Summer St Stamford CT
Free cancellation
Reserve now, pay when you stay
The price is CA $223 per night
CA $223
CA $256 total
Dec 3 - Dec 4
includes taxes & fees
Book a stay at this business-friendly hotel in Stamford. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hand & Stone Massage and Facial Spa and E. Gaynor Brennan Golf Course are located nearby.
Pool
Hot tub
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 $151 per night
CA $151
CA $173 total
Dec 6 - Dec 7
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.
Pool
Pet-friendly
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 $122 per night
CA $122
CA $140 total
Dec 6 - Dec 7
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 Rotary Park and E. Gaynor Brennan Golf Course are located nearby.
Breakfast included
Pet-friendly
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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 $884. 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 cannon on a stone pedestal by the sea.
A calm river reflecting buildings and trees, with a clear sky above.
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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