Westport Vacations from ￥235,058
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The Latest Westport Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Modern Comfort in the Heart of NYC
Southeast Yonkers
￥261,988
per person
Nov 10 - Nov 14
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.
Reviewed on Jun 29, 2026
Uscale 2BR Escape in the Heart of NYC
Bryn Mawr
￥262,242
per person
Nov 10 - Nov 14
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to White Plains (HPN)
8/10 Very Good! (1 review)
The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays.
Reviewed on Feb 21, 2026
Luxury 1BR located in Prime Yonkers Area
Bryn Mawr
￥265,870
per person
Nov 10 - Nov 14
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to White Plains (HPN)
4.8/10 (6 reviews)
C completely misrepresented did not stay there far from a luxury apartment advised to check into a different location no code or communication prior to check in time at 4 PM. Received emails and poor communication after 6:30 PM apartment smelled very musty and like a dead body was inside, extremely unprofessional and horrible experience.
Reviewed on May 5, 2026
Find the Best Westport Vacation Packages
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 5 kilometers 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 inches 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 Hotel Deals
Delamar Westport
1595 Post Rd E Westport CT
￥50,936
￥60,967 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (124 reviews)
"Great experience at this boutique hotel! Clean and chic and much better than any hotels around"
Reviewed on Aug 17, 2026
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
￥28,349
￥32,602 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (1,107 reviews)
"All good"
Reviewed on Aug 18, 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
￥23,754
￥27,317 total
Sep 1 - Sep 2
includes taxes & fees
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)
This 29-acre shoreline park offers pristine sandy beaches and stunning views of Long Island Sound. Enjoy swimming, volleyball, or simply relax on the boardwalk while watching sailboats drift across the horizon.
Levitt Pavilion
10.0/10 (7 reviews)
Nestled along the Saugatuck River, this outdoor venue has offered free summer concerts since 1974. Bring a picnic blanket and enjoy diverse musical performances under the stars.
Westport Country Playhouse
9.8/10 (6 reviews)
This historic theater, converted from an 1835 tannery, presents acclaimed productions in an intimate setting. Enjoy performances in a venue blending historic charm with modern comfort.
Westport Arts Center
Enjoy an outing to Westport Arts Center during your stay in Westport. Wander the waterfront or discover the area's sunsets.
Westport Historical Society
10.0/10 (3 reviews)
The Wheeler House showcases Westport's agricultural and maritime heritage through engaging exhibits. Explore this historical gem through guided tours and events that illuminate Connecticut's past.
Burying Hill Beach
10.0/10 (3 reviews)
This serene shoreline park offers a tranquil mix of sandy and rocky beach areas along Long Island Sound. Enjoy picnicking at tables overlooking the wildlife area or explore the coastal landscape at your leisure.
Westport Farmers Market
9.6/10 (5 reviews)
The Westport Farmers' Market offers 50+ vendors selling non-GMO, local produce and artisanal goods since 2006. Enjoy live music while browsing colorful stalls of fresh fruits, vegetables, and gourmet foods.
Alvord Beach
8.8/10 (3 reviews)
Tucked within Sherwood Island State Park, Alvord Beach offers a serene Connecticut shoreline with picturesque coastal views. Enjoy swimming in clear waters or a leisurely picnic against the backdrop of Long Island Sound.
Frequently asked questions
How much does a Westport vacation package cost?
You can pick up a vacation package to this popular destination from ￥235,058 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?
February, June and August are the best times to look for cheap Westport vacation packages. Opting to travel in quieter months means you can generally find better prices on hotels and flights.
How many days is enough for Westport?
We recommend booking a Westport vacation for a minimum of 2 days. This will give you enough time to check off popular sights such as Burying Hill Beach and Alvord Beach, as well as check out neighborhoods like Cranbury and Greens Farms. You might even be able to slot in a day trip or two from Westport.
Is it worth booking a vacation package to Westport?
Westport has all the ingredients you need for a fantastic getaway — golfing, history and nature are just the start. Whether you'd like to check out attractions like Compo Beach and Levitt Pavilion, or venture off the beaten track, you'll find plenty to experience on your Westport vacation.
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?
- Choose your travel dates: The things you'd like to do in Westport and your favorite season can help you decide when to travel.
- Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Westport. Then, pick a hotel that suits your budget, whether that's an affordable stay or a lavish getaway.
- Determine how many days away: Start by making a list of all the activities and attractions you want to experience in Westport. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Westport vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
