Westport Vacations from ￥277,226

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The Latest Westport Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Yonkers - Westchester

Hampton Inn & Suites Yonkers - Westchester

2.5 out of 5
Northeast Yonkers
Price was ￥300,615, price is now ￥277,226 per person
￥277,226
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to White Plains (HPN)
9/10 Wonderful! (1,077 reviews)
This hotel was clean from the lobby to the room. Exceptional service and the free breakfast was a plus

Reviewed on Jul 3, 2026

Courtyard by Marriott Stamford Downtown

Courtyard by Marriott Stamford Downtown

3 out of 5
Downtown Stamford
Price was ￥341,210, price is now ￥318,079 per person
￥318,079
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to White Plains (HPN)
9/10 Wonderful! (873 reviews)
It was just a room. No luxuries, bad towels and had to ask for more. Nothing to brag about! $37 per day parking $32 + $5 tip. No microwave and the fridge froze my leftovers.

Reviewed on Jun 22, 2026

Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County

3 out of 5
Price was ￥324,874, price is now ￥304,801 per person
￥304,801
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to White Plains (HPN)
9/10 Wonderful! (1,004 reviews)
In addition to being a well-run hotel, the setting was unique and gracious.

Reviewed on Jul 2, 2026

Hyatt Place New York/Yonkers

Hyatt Place New York/Yonkers

3 out of 5
Southeast Yonkers
Price was ￥308,325, price is now ￥290,978 per person
￥290,978
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to White Plains (HPN)
9.2/10 Wonderful! (1,501 reviews)
Ty

Reviewed on Jun 29, 2026

Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown

3.5 out of 5
Price was ￥327,439, price is now ￥317,421 per person
￥317,421
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to White Plains (HPN)
9.4/10 Exceptional! (1,003 reviews)
Hotel was great and staff was very friendly. The valet parking is kind of a bummer although they were friendly…

Reviewed on Jul 4, 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

Delamar Westport

4 out of 5
1595 Post Rd E Westport CT
The price is ￥49,491 per night from Jul 6 to Jul 7
￥49,491
￥59,333 total
Jul 6 - Jul 7
includes taxes & fees
9.6/10 Exceptional! (95 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 ￥37,915 per night from Jul 26 to Jul 27
￥37,915
￥43,602 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,051 reviews)
"Loved the beautiful botanical interior. The pool and hot tub were nice after a long day. Then the bar and food were good too. The gym was perfect for morning WO. Great day spent ."

Reviewed on Jul 2, 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 ￥16,408 per night from Jul 5 to Jul 6
￥16,408
￥18,870 total
Jul 5 - Jul 6
includes taxes & fees
6.6/10 (1,505 reviews)
"The place was gross and I got stuck in the elevator and had to pry open the doors leaving myself with cuts on my forearms. The place should be closed down."

Reviewed on Jul 2, 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,094 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 from ￥277,226 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.

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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.