Book Exclusive Westport Vacation Packages

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Westport flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
Price was CA $1,149, price is now CA $933 per person
CA $933
per person
May 15 - May 18
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Book a stay at this 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.
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3 out of 5
Southeast Yonkers
Price was CA $8,090, price is now CA $5,094 per person
CA $5,094
per person
Jun 18 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
Stay at this vacation home in Yonkers. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Price was CA $1,688, price is now CA $1,112 per person
CA $1,112
per person
May 16 - May 20
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) 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.
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
Price was CA $1,341, price is now CA $1,084 per person
CA $1,084
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
Book a stay at this business-friendly hotel in White Plains. Enjoy free WiFi, breakfast (surcharge), and free airport pick-up. Our guests praise the bar and the helpful staff in our reviews. Popular attractions The Westchester Mall and Westchester County Center are located nearby.
Westchester Marriott

Westchester Marriott

4.5 out of 5
Price was CA $1,293, price is now CA $1,057 per person
CA $1,057
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 Skating Academy and Westchester Broadway Theatre 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 $301 per night
CA $301
CA $368 total
Apr 20 - Apr 21
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
Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.

Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.

Westport CT
Get rates
Stay at this vacation home in Westport. Enjoy a fitness center, laundry facilities, and in-room fireplaces. Popular attractions Westport Historical Society and Westport Country Playhouse are located nearby.
Pool
Hot tub
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $162 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Milford Plaza Shopping Center are located nearby.
Breakfast included
Pet-friendly
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Free cancellation
Reserve now, pay when you stay
The price is CA $86 per night
CA $86
CA $99 total
Apr 19 - Apr 20
includes taxes & fees
Book a stay at this business-friendly motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Silver Sands State Park and Walnut Beach are located nearby.
Pet-friendly
Parking included
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Free cancellation
Reserve now, pay when you stay
The price is CA $188 per night
CA $188
CA $216 total
Apr 5 - Apr 6
includes taxes & fees
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Roosevelt Forest and Beardsley Zoo are located nearby.
Pool
Hot tub
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue Norwalk CT
Free cancellation
Reserve now, pay when you stay
The price is CA $174 per night
CA $174
CA $200 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Norwalk Islands and Stepping Stones Museum for Children are located nearby.
Parking included
Free WiFi
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See all available properties in Westport
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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

Sherwood Island State Park from Compo Beach, CT, USA

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

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

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?
Your travel daydreams can become a reality in Westport from as little as CA $933. 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

View across the Saugatuck River from Westport toward industrial buildings
Cannons at Compo Beach, CT, USA
Fluffy sunset at the beach
Westport
Westport

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