Westport Vacations from $271

Book a Hotel + Flight or Car together to unlock savings

Photo by Marina Timo

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Westport Vacation

Reserve a Westport vacation package and prepare to experience all this city has to offer. Think about staying in the neighborhood of Downtown Stamford, which is good for history, bars and pubs and dining. Make your trip to Westport even more fulfilling by including some sightseeing. Fairfield University, Norwalk Maritime Aquarium and Compo Beach are among the leading attractions you'll want to explore. Expedia can help you escape your routine. Tailor your vacation to Westport to suit your style of travel, whatever that may be.

The Latest Westport vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Price was $371, price is now $271 per person
$271
per person
Jan 30 - Feb 2
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
8/10 Very Good! (1,264 reviews)
Bed was comfortable, room clean,

Reviewed on Dec 24, 2025

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,120, price is now $1,451 per person
$1,451
per person
Mar 2 - Mar 9
found 12 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to White Plains (HPN)
No reviews
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
Ridgeway-Bullshead
Save 100% on your flight
Price was $412, price is now $284 per person
$284
per person
Feb 3 - Feb 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
7.8/10 Good! (674 reviews)
Overall the hotel was decent but if like me you have any sensitivy to the toxic chemicals in perfumes, be warned they use a super strong perfumed air freshener in all rooms and you have no ability to open a window. This gave me a headache from the second I checked in that didn’t go away. The staff was mediocre-to-lazy in terms of service. I found myself a couple occasions (including check in at 6pm) waiting at the front desk with no one there. The person was on their cellphone once with a friend and continued talking loudly to the friend throughout their entire conversation with me. The whole lobby had the air of a large casino or resort lobby that had been partially abandoned. The breakfast buffet was nice. The location was convenient for where I needed to be. They have a gigantic garage but the parking costs money.

Reviewed on Dec 20, 2025

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
Cranbury
Price was $387, price is now $274 per person
$274
per person
Jan 30 - Feb 2
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
8.4/10 Very Good! (1,012 reviews)
This was our second stay here - clean, well-stocked and friendly staff. Easy parking. We'll stay again!

Reviewed on Dec 26, 2025

Don't see what you're looking for?
See all available trips from Columbus to Westport
View all trips

Discover the most popular places to visit in Westport

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

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 Hotel Deals

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Jan 1 to Jan 2
$123 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.2/10 Very Good! (1,029 reviews)
Great hidden gem

Reviewed on Dec 16, 2025

EVEN Hotel Norwalk by IHG
DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

3.5 out of 5
1 First Stamford Pl Stamford CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Jan 4 to Jan 5
$155 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
Overall it was a good place to stay

Reviewed on Dec 17, 2025

DoubleTree by Hilton Stamford
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $121 total per night from Jan 24 to Jan 25
$121 total
Jan 24 - Jan 25, 2026
Total with taxes and fees
8.4/10 Very Good! (1,731 reviews)
Clean room and friendly staff. Great inexpensive hotel. We’ll be back

Reviewed on Dec 26, 2025

Amsterdam Hotel
See all 1,084 properties in Westport
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.

Find the Best Westport Vacation Packages

Things to do in and around Westport

Westport offers a delightful mix of outdoor fun, family-friendly activities, and romantic getaways. Enjoy popular attractions like local theaters and recreational areas, perfect for both relaxation and entertainment. Don't miss the chance to surf on weekends, adding an adventurous twist to your visit. Whether you're exploring educational sites or soaking up the vibrant atmosphere, Westport has something for everyone.

Shopping

In Westport, you can shop at Caldor Shopping Center, only 3 miles away, offering a mix of family and city vibes. The Westport Farmers Market provides a local experience right in town. If you're up for a drive, check out The SoNo Collection, located 4 miles away, featuring entertainment and diverse shopping options.

Recreation

At Hartford HealthCare Amphitheater, enjoy invigorating outdoor events with a vibrant sports atmosphere, just a short drive from Westport. The Levitt Pavilion offers soothing evenings filled with music and entertainment, while the Westport Country Playhouse provides a charming cultural experience perfect for families and romantic outings.

Adventure

Experience the thrill of ziplining at The Adventure Park at Discovery Museum, located 8 miles from Westport. Enjoy fruit picking at Blue Jay Orchards, 18 miles away, or hike the scenic Ives Trail, 16 miles from town, surrounded by beautiful outdoor landscapes.

Nightlife

Westport's nightlife offers a vibrant atmosphere with cozy bars and lively restaurants. Enjoy craft cocktails at The Whelk, or try the local flavors at Elvira's. For a more relaxed vibe, visit Saugatuck Craft Butchery for artisanal bites and great wines.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Westport

Westport, Connecticut, is perfect for outdoor, family, and romantic getaways. Visitors can explore beautiful beaches, urban parks, and modern colleges and universities. The area's attractions provide a rich cultural experience, making it an ideal destination for travelers seeking adventure and relaxation. Whether you’re looking to spend quality time with family or enjoy a romantic escape, Westport offers a variety of activities to suit every preference.

  • Fairfield University: Experience the vibrant atmosphere of this modern university located just 5 miles from Westport. With its beautiful campus and engaging events, you can soak in the city vibes while exploring art exhibits, lectures, and student performances.
  • Compo Beach: Enjoy a relaxing day at Compo Beach, nestled within Westport. This picturesque beach offers stunning views, soft sands, and various recreational activities, making it the perfect spot for sunbathing, swimming, or picnicking with family and friends.
  • Historic South Norwalk: Discover the charm of Historic South Norwalk, located 4 miles from Westport. This area is rich in culture, featuring historic architecture, delightful shops, and restaurants that showcase the local heritage, perfect for a leisurely stroll.

Best time to go to Westport

The best time to visit Westport can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Westport falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Westport falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.5°F (-0.3°C)Light RainMostly SunnySlightly LowSlightly Low
February32.7°F (0.4°C)Light RainMostly SunnySlightly LowSlightly Low
March39.2°F (4.0°C)Light RainMostly SunnyAverageSlightly Low
April49.5°F (9.7°C)Light RainMostly SunnySlightly HighAverage
May59.4°F (15.2°C)Light RainMostly SunnySlightly HighSlightly High
June68.4°F (20.2°C)Light RainMostly SunnyAverageSlightly High
July75.4°F (24.1°C)Light RainMostly SunnySlightly HighSlightly High
August74.1°F (23.4°C)Light RainMostly SunnyAverageAverage
September67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
October57.4°F (14.1°C)Light RainMostly SunnySlightly LowAverage
November45.9°F (7.7°C)Light RainMostly SunnyAverageAverage
December37.9°F (3.3°C)Light RainMostly SunnyAverageAverage

Tips to save on your trip to Westport

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Westport.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Westport Beach Vacation

A Westport vacation makes it simple to kick back and unwind. Whether you like the thought of sitting around by the water's edge or wandering along the shoreline collecting seashells, a trip to Westport is difficult to say no to. If you want to be close to the town center, stay in the vicinity of Compo Beach. This strip of coast is only 3 miles away. We also offer Westport vacation packages around Burying Hill Beach and Alvord Beach, two other stunning nearby options.

Things You Should Know About Westport

  • Book one of our Westport beach hotels to enjoy this destination at its very best. Wander along the water's edge and be amazed by the stunning sunsets just steps from your doorstep.
  • You can also browse our range of private vacation homes. They're popular with people planning a stay in Westport. Check out Inn at Longshore and The Westport Inn, an Ascend Collection Hotel.
  • Be sure to visit our Westport things to do page for some trip planning inspiration. With a population of around 26,400 in Westport, we're sure there'll be a few locals who'll be happy to give you some extra advice!
  • Get some great deals with a Westport vacation package. With all that extra cash in your pocket, you won't regret indulging in this destination's best offerings. Compo Beach, Compo Beach and Levitt Pavilion are excellent places to start.

Westport Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Population
26,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Jennings Beach, Norwalk Maritime Aquarium and Compo Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Westport vacation package cost?
You can pick up a vacation package to this popular destination from $271 on Expedia. However, how much your vacation to Westport costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Westport?
You can usually find lower prices and better availability in April, May and November. Check out our cheap Westport vacation packages and you could land some excellent off-season deals.
How many days is enough for Westport?
Allow at least 2 days for your Westport vacation in order to enjoy everything that makes this place unique. Wander around popular neighborhoods, including Cranbury and Greens Farms. Then check out top attractions such as Burying Hill Beach and Alvord Beach. With a well-planned itinerary, you can keep busy with room for some relaxation too. Want to travel beyond Westport? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Westport?
Whether you'd like to explore top sights such as Compo Beach and Levitt Pavilion on your Westport vacation, or coming for its excellent golfing, history and nature, there's something for everyone here. With so much to do, you'll soon learn why so many visitors think Westport is a good vacation destination.
How to find the best Westport package deals?
Start your search for a Westport package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Westport package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Westport escape off to a flying start.
Is it cheaper to book a Westport vacation as a package?
You can enjoy significant savings on your next Westport escape by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Westport?
If you're planning an impromptu Westport vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Westport?

  1. Choose your travel dates: What you'd like to do in Westport and your favorite season will help you decide when to travel.
  2. Set your budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Westport. Then, pick a property that suits your budget, whether that's an affordable stay or a high-end getaway.
  3. Use our trip planning tool to discover Westport: Research every aspect of your trip to Westport with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by making a list of all the activities and sights you want to get to in Westport. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Westport vacation package.
  6. Add on excursions and experiences: Read our travel guide to find some incredible things to do in Westport. Book tickets or make reservations as soon as you can to save time and avoid the stress of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Westport vacation packages?
Set off on your perfect trip to Westport with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or hold off until your next paycheck — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snap up travel deals while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.