Westport Holidays from £852
Book a Hotel + Flight or Car together to unlock savings
Your Westport Holiday
Reserve a Westport holiday package and prepare to experience all this city has to offer. Think about staying in the neighbourhood 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 holiday to Westport to suit your style of travel, whatever that may be.
Top Westport Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Modern Comfort in the Heart of NYC
Southeast Yonkers
£852
per person
2 Nov - 8 Nov
found 20 hours ago
Return flight included
Manchester (MAN) 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 29 Jun 2026
Upscale Modern Luxury 3BR Home
£1,366
per person
31 Oct - 7 Nov
just found
Return flight included
London (LHR) to White Plains (HPN)
4/10 (1 review)
Property was missing needed items and it took two days to get them(coffee maker). For the price you get what you’d expect. Older property with some updates needed. Everything worked but older appliances.
Reviewed on 23 Jan 2026
Luxury 3BR Family Home Game Room Parking
Bryn Mawr
£1,066
per person
31 Oct - 7 Nov
found 1 hour ago
Return flight included
London (LHR) to White Plains (HPN)
6.8/10 (3 reviews)
This is a scam. Arrived at the supposed address only to be met by the owner of the property nextdoor informing me that address did not exist and unfortunately we weren’t the only ones that experienced this. Was a a terrible start to a family vacation, luckily a Hampton inn was right down the road and had vacancies so were able to book same day.
Reviewed on 29 Aug 2026
Westport Beach Holiday
Salty sea air and gorgeous ocean views are some things to look forward to on your Westport holiday. If you want to save on your trip to Westport, we'll let you in on a secret — book one of our Westport holiday packages. Lock in one near Compo Beach, only 2 miles from the downtown area and a must-do while here. Alternatively, select a package that puts you close to Burying Hill Beach, another beautiful strip of coast. Whichever you choose, you'll be left with extra money in your travel budget to spend.
Westport Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Westchester County Airport (HPN) |
Population | 26,400 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Norwalk Maritime Aquarium, Compo Beach and Jennings Beach |
Top hotels in Westport
Delamar Westport
1595 Post Rd E Westport CT
£208
27 Sept - 28 Sept
includes taxes & fees
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
£166
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (1,124 reviews)
"Great hotel, great location! Our go-to halfway point to stay the night."
Reviewed on 31 Aug 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
£127
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"Website said there was a hot tub but there wasn’t one. Otherwise it was a good experience."
Reviewed on 30 Aug 2026
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 theatre, converted from an 1835 tannery, presents acclaimed productions in an intimate setting. Enjoy performances in a venue blending historic charm with modern comfort.
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 colourful stalls of fresh fruits, vegetables, and gourmet foods.
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 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.
Frequently asked questions
How much does a Westport travel package cost?
The most affordable Westport travel package is £852, so your dream holiday can become a reality — without burning a hole in your pocket. Bundle flights, hotels, car rentals and more to create a package that suits your travel style.
If I'm not able to travel, can I cancel my Westport travel package?
Your situation can change without warning, so yes, you can. You may be able to cancel and rebook your Westport travel package for free within 24 hours of booking. For older bookings, you can still make changes, but your car rental company, hotel or airline may impose a fee. Looking for more information? Have a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Westport?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got it all. Choose the combination that suits you and watch your savings grow. Of course, a travel package is never one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 hotels from all over the world, which lets you customize your Westport getaway.
Does Expedia offer Book Now, Pay Later Westport holidays?
Good news! We do. Expedia has teamed up with online lender Klarna to help you easily pay for your holiday in instalments. Simply click on the payment plan that suits you best during checkout and take the stress out of budgeting for your next trip. Be sure to bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your holiday buck. Browse our flexible payment options below:
- Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your trip over multiple transactions.
- Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan with Klarna.
Where should I stay in Westport?
A trip to Westport wouldn't be complete without stopping by Westport Country Playhouse, Compo Beach and Levitt Pavilion. Spend your nights near these tourist attractions and make sightseeing easy.
What are the top hotels in Westport?
Sunny Studio Apt Above Historic Westport Mill in the Greens Farms neighbourhood is a fantastic choice for a Westport escape. Book a room here and you'll be well-placed to get out and discover all that this city has to offer.
How far in advance should I book my Westport holiday?
While not all air carriers release tickets early, it's usually possible to look up international airfares on Expedia up to 12 months in advance. This is the time you can score some incredible bargains. If you're purchasing tickets last minute, there's a chance you could get lucky. Sometimes the lowest prices become available just weeks prior to departure.
What does an Expedia Westport travel package include?
Flights, hotels and rental cars, or any combination of the three — the choice is all yours! Whether you're venturing to Westport with the family or travelling by yourself, there's a package to fit your budget and style. Once you've made your booking, why not add on a couple of tours as well?
What should I know before booking a Westport travel package?
You can save big by bundling your airfares, hotels and rental cars. Once you've created your package, you can add on things like activities or sightseeing tours. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Westport Expedia travel package?
Yes, so take your pick! We have access to over 550 partner airlines around the world, so you can tailor your Westport getaway according to your travel preferences.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.