Westport Vacation Packages

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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.

Top Westport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Modern Comfort in the Heart of NYC
Luxury 3BR Family Home Game Room Parking
Luxury NYC Home Game Room Free Parking
Luxury 3BR Home Game Room Free Parking
3BR Prime Luxury near NYC w Arcade Room

Things to do in and around Westport

Westport, Connecticut, is an ideal destination for outdoor and romantic getaways, boasting stunning scenery. Visitors can enjoy whale watching, relaxing on the beach, and engaging in various beach activities. Additionally, the area features recreational spots and a golf course, along with fun activities like a guided scavenger hunt in Bridgeport. With its blend of nature and adventure, Westport offers an enriching experience for all tourists.

Shopping

In Westport, you can enjoy shopping at the Westport Farmers Market for local goods. For a broader selection, visit Center Seven Shopping Center, only 4.8km away, or Springdale Shopping Center, 14.5km away, which offers a variety of shops and family-friendly vibes.

Recreation

The Hartford HealthCare Amphitheater offers an energetic atmosphere, perfect for sports enthusiasts looking to enjoy live events. For a cultural experience, the Downtown Cabaret Theatre provides a romantic setting with diverse entertainment options. Meanwhile, the Levitt Pavilion hosts captivating concerts, creating an enjoyable ambiance for music lovers in Westport.

Adventure

Experience the thrill of ziplining and navigating ropes courses at The Adventure Park at Discovery Museum, located 12.9km from Westport. For a fun outdoor tennis experience, visit Scalzi Park Tennis Center, 17.7km away. Explore the scenic Blue Jay Orchards, situated 112.9km from Westport for a delightful retreat.

Nightlife

In Westport, Connecticut, enjoy a vibrant nightlife with venues like The Westport Country Playhouse for live theatre, or grab a drink at the local bars along Main Street. Explore the lively atmosphere at Compo Beach during summer nights, where social gatherings and music create a festive spirit.

*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 an ideal destination for outdoor enthusiasts and romantics alike, boasting beautiful beaches, urban parks, and modern colleges. Visitors can explore popular attractions such as Compo Beach, the picturesque Westport Marina, and Westport House, which offers a rich cultural experience. With its blend of scenic views and family-friendly activities, Westport promises an enjoyable getaway for travelers looking to immerse themselves in nature and local charm.

  • Compo Beach: Experience the quintessential beach vibes at Compo Beach, a local favourite in Westport. With its sandy shores, picnic areas, and scenic views of Long Island Sound, it’s perfect for sunbathing, swimming, or simply relaxing with family and friends.
  • The Glass House: Located 14.5km from Westport, this unique museum showcases modern architecture and design. The Glass House offers guided tours that immerse you in the cultural significance of its transparent structure, blending art with nature in a stunning setting.
  • Sheffield Island Lighthouse: A historic gem situated 11.3km from Westport, Sheffield Island Lighthouse invites you to explore its rich maritime history. Enjoy scenic boat rides to the island, where you can appreciate the stunning coastal views and learn about its significance in navigation.

Best time to go to Westport

The best time to visit Westport is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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 centre, stay in the vicinity of Compo Beach. This strip of coast is only 5 kilometres 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 67,056 cm 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.

Ready to book your vacation to Westport?

 

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Westport Hotel Deals

Delamar Westport

Delamar Westport

4 out of 5
1595 Post Rd E Westport CT
The price is CA $292 per night from May 5 to May 6
CA $292
CA $356 total
May 5 - May 6
includes taxes & fees
9.6/10 Exceptional! (51 reviews)
Everything was terrific

Reviewed on Apr 10, 2026

Delamar Westport
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
Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
The price is CA $85 per night from Apr 28 to Apr 29
CA $85
CA $98 total
Apr 28 - Apr 29
includes taxes & fees
6.4/10 (1,008 reviews)
The best part of my state was the lady that checked me in she was very amazing she was the only one there but she got her job done she was very instrumental and very excellent horrible position

Reviewed on Apr 12, 2026

Motel 6 Milford, CT
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.

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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.