Westport Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Westport Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Amsterdam Hotel
Downtown Stamford
$513
per person
Oct 3 - Oct 7
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Center for the Arts are located nearby.
Luxury NY Home with Free Parking
$3,047
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to White Plains (HPN)
Book a stay at this family-friendly vacation home in White Plains. Enjoy free parking, dry cleaning or laundry services, and laundry facilities. Popular attractions Westchester County Center and Silver Lake Park are located nearby.
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.
Reviewed on Nov 8, 2025
Tarrytown House Estate
$991
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to White Plains (HPN)
Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Westchester County Center and Lyndhurst Mansion are located nearby.
Luxury NY Home 3BR with Easy Parking
Southeast Yonkers
$2,728
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to White Plains (HPN)
Book a stay at this business-friendly vacation home in Yonkers. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Bronx Zoo and Empire City Casino are located nearby.
Luxury NYC Home Game Room Free Parking
$1,598
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to White Plains (HPN)
Stay at this villa in White Plains. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Westchester County Center and Silver Lake Park are located nearby.
After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is that there was a plumbing problem and they would get us to another property from the original property manager and Expedia NOT doing a thing to help 4 of us stranded with no place to stay, we got to the other property. The new property was fine, but the most upsatting thing was dealing with Expedia trying to get a place for us to stay. Expedia tried saying they would cancel the accommodations and get us a Hotel but we would have to pay for the hotel and then wait for any credits or refund on our original booking. HIGHLY unacceptable by Expedia customer service. I am a GOLD member and spend quite a few thousand dollars a year for both business and pleasure and they did NOTHING to make me feel they were taking care of us. We basically lost a day of full work which cost my business over $1500 in non productive work.
Reviewed on May 4, 2026
Hyatt Regency Greenwich
$867
per person
Oct 3 - Oct 7
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Mianus Park are located nearby.
Yes
Reviewed on Aug 22, 2026
Westport Vacation Packages
Trying to save money and time on your upcoming vacation to Westport? Then look no further, as the AARP Travel Center Powered by Expedia® is here to help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Westport incredible. Our Travel Center is a one-stop shop where you can put together the best vacation package for you and your family. AARP Travel Center has an amazing selection of flights and lodgings, as well as Westport activities to select from.
Westport Hotel Deals
You can choose from around 1098 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Westport hot spots, we have plenty of options available.
We have fantastic rates on everything from family-friendly resorts that meet all the vacation must-haves to affordable accommodations perfect for those on looking to save. You can search all the options and choose the lodging that is ideal for you. With AARP Travel Center's Westport hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Westport
Westport has about 27,899 people that call this city their home. If you needed a break from the hustle of a big city, then you are in the right spot. If you are unsure where to start, head towards the town center. You'll usually find some great restaurants and some stores worth exploring. A lot of visitors appreciate the location close to New York City.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Book Together and Save
With so much going on in Westport, you'll be wanting to plan your outings, not spending time to finding the cheapest hotel. AARP Travel Center allows you to quickly get everything you wish for, and save money doing it. You can coordinate your whole trip, including activities in Westport from only one place. The hardest packing you'll have to do is for your suitcase. Bundle today and save!
Top Hotel Deals
Delamar Westport
1595 Post Rd E Westport CT
Stay at this hotel in Westport. Enjoy free breakfast, free valet parking, and free train station pick-up. Popular attractions Southport Beach and Burying Hill ...
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff ...
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
EVEN Hotel Norwalk by IHG
426 Main Ave, Route 7 Norwalk CT
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
La Quinta Inn & Suites by Wyndham Stamford / New York City
135 Harvard Avenue Stamford CT
Stay at this hotel in Stamford. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Norwalk Inn & Conference Center
99 East Avenue Norwalk CT
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
Amsterdam Hotel
19 Clarks Hill Ave Stamford CT
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Circle Hotel Fairfield
417 Post Road Fairfield CT
Book a stay at this beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Motel 6 Milford, CT
111 Schoolhouse Road Milford CT
Book a stay at this business-friendly motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Hartford HealthCare Amphitheater ...
Danfords Hotel and Marina
25 E Broadway Port Jefferson NY
Stay at this hotel in Port Jefferson. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Red Carpet Inn
1209 E Main St Stamford CT
Stay at this hotel in Stamford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Chelsea Piers and Cove Island Park are located ...
Hyatt Place Milford / New Haven
190 Old Gate Lane Milford CT
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Watershed
353 Main Ave Norwalk CT
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean ...
Red Roof Inn Milford - New Haven
10 Rowe Ave Milford CT
Stay at this hotel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Sep 14 - Mon, Sep 28
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$180
Roundtrip
found 11 hours ago
Mon, Sep 14 - Mon, Oct 5
CLT
Charlotte-Douglas Intl.
ISP
MacArthur
$188
Roundtrip
found 2 days ago
Mon, Sep 14 - Mon, Sep 28
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$246
Roundtrip
found 11 hours ago
Wed, Oct 14 - Sat, Oct 31
DJT
President Donald J. Trump Intl. Airport
ISP
MacArthur
$257
Roundtrip
found 4 days ago
Mon, Sep 14 - Tue, Sep 22
CLT
Charlotte-Douglas Intl.
ISP
MacArthur
$258
Roundtrip
found 2 hours ago
Best neighborhoods in Westport
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