Westport Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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    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 Hotel Deals

Delamar Westport

Delamar Westport

4 out of 5
1595 Post Rd E Westport CT
The price is AEDĀ 1,060 per night from Aug 3 to Aug 4
AEDĀ 1,060
AEDĀ 1,274 total
3 Aug - 4 Aug
includes taxes & fees
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 AEDĀ 680 per night from Aug 9 to Aug 10
AEDĀ 680
AEDĀ 781 total
9 Aug - 10 Aug
includes taxes & fees
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 AEDĀ 364 per night from Aug 17 to Aug 18
AEDĀ 364
AEDĀ 418 total
17 Aug - 18 Aug
includes taxes & fees
6.6/10 (1,546 reviews)
"The property is being renovated, however it is above average. The Staff is very helpful and most importantly the room was clean"

Reviewed on 16 July 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,103 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?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Westport costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Westport?
If you're hoping to book a cheap Westport vacation package, consider visiting in February, June and August. You'll typically find lower prices on hotels and airfares during these months ā€” perfect for budget-conscious travelers.
How to find the best Westport package deals?
Begin 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 discover offers that come with huge savings. If you don't find the perfect Westport package deal right 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 adventure underway.
Is it cheaper to book a Westport vacation as a package?
You can enjoy significant savings on your next Westport getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Westport?
If you've got your Westport vacation dates finalized, book early to snap up some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Westport?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Westport.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to Westport.
  3. Set the duration of your trip: Start by listing all the activities and attractions you want to get to in Westport. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Westport vacation package that brings all your bookings together.