Westport Vacations from $287

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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.
Courtyard by Marriott Poughkeepsie
Stamford Suites
The Armon Stamford Hotel & Conference
Courtyard by Marriott Yonkers Westchester County
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Discover the most popular places to visit in Westport

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 refundable
$131 nightly
The price is $151 total per night from Feb 15 to Feb 16
$151 total
Feb 15 - Feb 16
Total with taxes and fees
8.2/10 Very Good! (1,057 reviews)
Good

Reviewed on Jan 11, 2026

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
$146 nightly
The price is $167 total per night from Jan 29 to Jan 30
$167 total
Jan 29 - Jan 30
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
The customer service was absolutely amazing

Reviewed on Jan 4, 2026

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 Feb 14 to Feb 15
$121 total
Feb 14 - Feb 15
Total with taxes and fees
8.4/10 Very Good! (1,732 reviews)
Clean room, nice view, courteous staff and smooth check-in/check-out experience. Breakfast was a nice compliment.

Reviewed on Jan 12, 2026

Amsterdam Hotel
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, Connecticut, offers a delightful blend of outdoor and romantic activities, making it an ideal vacation spot. Visitors can explore beautiful scenic areas, enjoy a round of golf, and take advantage of the local recreational facilities. Popular attractions and entertainment options abound, providing plenty of outdoor fun, especially during surf weekends. Don't miss out on the charming atmosphere and engaging experiences that Westport has to offer.

Shopping

The Westport Farmers Market offers a vibrant local shopping experience with a mix of fresh produce and artisan goods. If you're up for a drive, the Stamford Town Center features a wide range of shops and entertainment just 11 miles away, while the Caldor Shopping Center is a convenient 3 miles from Westport.

Recreation

Experience invigorating events at the Hartford HealthCare Amphitheater, just 9 miles from Westport, where the electric sports atmosphere will uplift your spirits. In Westport, enjoy live performances at the Levitt Pavilion for entertainment vibes, or immerse yourself in culture and romance at the Westport Country Playhouse theater.

Adventure

Experience the thrill of ziplining and navigating ropes courses at The Adventure Park, 8 miles from Westport. Explore the scenic beauty of Blue Jay Orchards, 18 miles away, and hike the Ives Trail, 16 miles from Westport, immersing yourself in the great outdoors.

Nightlife

Westport offers a vibrant nightlife scene with venues like The Whelk for inventive seafood and cocktails, and Rive Bistro for a cozy dinner. For a lively atmosphere, check out The Black Duck Café, perfect for casual drinks and live music on weekends.

*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 a perfect destination for outdoor and romantic getaways, offering stunning scenery and a variety of attractions. Visitors can enjoy the beautiful beaches, explore urban parks, and experience the vibrant culture around modern colleges and universities. Whether you're looking for family-friendly activities or cultural experiences, Westport has something to offer for every traveler seeking adventure and relaxation.

  • Compo Beach: Enjoy a classic beach experience at Compo Beach, known for its sandy shores and vibrant beach vibes. Perfect for sunbathing, swimming, or picnicking, this local gem offers stunning views of the Long Island Sound.
  • Historic South Norwalk: Located 4 miles from Westport, this charming area brims with culture. Stroll through its historic streets, admire the architecture, and visit local shops and eateries that celebrate its rich heritage.
  • Bridgeport Downtown South Historic District: Just 9 miles away, this historic district showcases the cultural tapestry of Bridgeport. Explore its well-preserved buildings, galleries, and theaters, making it a vibrant spot for history and arts enthusiasts.

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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Westport.
  • Consider traveling to Westport during the low season (January to March) for more affordable options.
  • 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

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Frequently asked questions

How much does a Westport vacation package cost?
You can pick up a vacation package to this popular destination from $287 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.

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