Westport Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 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

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

Delamar Westport

4 out of 5
1595 Post Rd E Westport CT
The price is ₩412,110 per night from Jul 12 to Jul 13
₩412,110
₩496,496 total
Jul 12 - Jul 13
includes taxes & fees
9.6/10 Exceptional! (96 reviews)
"Enjoyed the breakfast buffet!"

Reviewed on Jul 3, 2026

Delamar Westport
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is ₩315,690 per night from Jul 26 to Jul 27
₩315,690
₩363,044 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,073 reviews)
"Beautiful hotel with a good restaurant"

Reviewed on Jul 9, 2026

Hyatt Regency Greenwich
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue Stamford CT
Fully refundableReserve now, pay when you stay
The price is ₩163,132 per night from Aug 2 to Aug 3
₩163,132
₩187,602 total
Aug 2 - Aug 3
includes taxes & fees
6.6/10 (1,529 reviews)
"This morning there was no water for the shower in the bathroom. No water hot or cold at all. We had to leave for the airport so we left without shower or shaving. It will be a long time before we come back here again."

Reviewed on Jul 9, 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,102 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.

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.
See properties

Frequently asked questions

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

  1. Choose your travel dates: The things you'd like to do in Westport and your favorite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.

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.