Westport Vacation Packages

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Your Westport Vacation

Reserve a Westport vacation package and prepare to experience all this city has to offer. Think about staying in the neighborhood 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 vacation to Westport to suit your style of travel, whatever that may be.

Top Westport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
Downtown Stamford
per person
Aug. 20 - Aug. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.4/10 Very Good! (1,504 reviews)
Good location. Reasonable continental breakfast.

Reviewed on Jun. 14, 2024

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Jul. 18 - Jul. 21
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
No reviews
Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains

2 out of 5
per person
Aug. 19 - Aug. 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
6.2/10 (1,001 reviews)
Ok for the Price and location

Reviewed on Jun. 10, 2024

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

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

2.5 out of 5
per person
Aug. 2 - Aug. 8
found 3 hours ago
Roundtrip flight included
Vancouver (YVR) to White Plains (HPN)
5.6/10 (1,073 reviews)
Needed to use freight elevator to transfer luggage cart to passenger elevator.stains n rips on carpet n blankets

Reviewed on Jun. 15, 2024

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
per person
Jul. 29 - Aug. 1
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to White Plains (HPN)
7.8/10 Good! (1,003 reviews)
I liked the layout of the room, it did seem a bit outdated but it still felt comfortable overall. The bathtub was very worn and had some old stains and cracks. The phone in my room didn't work, and I hadn't noticed until I tried calling the front desk the day after checking in. Some of the staff were very kind and helpful. It's about a 10-minute walk to the train station, which worked for me but could be a dealbreaker for those with mobility issues. My biggest issue was the wifi, it did not work for me at all. It was pretty useless on my laptop and so-so on my phone, but I ended up just using my data after a while. I decided to check out early because I really needed reliable wifi for my trip and it wasn't worth it trying to find a coffee shop or public space whenever I needed to use my laptop.

Reviewed on Jun. 13, 2024

Westport Beach Vacation

Salty sea air and gorgeous ocean views are some things to look forward to on your Westport vacation. If you want to save on your trip to Westport, we'll let you in on a secret — book one of our Westport vacation packages. Lock in one near Compo Beach, only 3 kilometres 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 Hotel Deals

Inn at Longshore
Inn at Longshore
2.5 out of 5
260 Compo Rd S, Westport, CT
The price is CA $232 per night from Jun. 17 to Jun. 18
CA $232
CA $267 total
includes taxes & fees
Jun 17 - Jun 18
9/10 Wonderful! (110 reviews)
"Lovely"

Reviewed on May 13, 2024

Inn at Longshore
Westport Paradise With Every Amenity!
Westport Paradise With Every Amenity!
Westport
The price is CA $803 per night from Jun. 16 to Jun. 17
CA $803
CA $1,154 total
includes taxes & fees
Jun 16 - Jun 17
10/10 Exceptional! (14 reviews)
Weekend Getaway
"The guest house was spacious and well appointed. The furnishings were very comfortable. The grounds at the house are beautiful. We thoroughly enjoyed our stay."

Reviewed on May 20, 2024

Westport Paradise With Every Amenity!
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Jun. 28 to Jun. 29
CA $133
CA $155 total
includes taxes & fees
Jun 28 - Jun 29
8.4/10 Very Good! (1,520 reviews)
"Great hotel for a night or extended stay . Professional staff , clean rooms and breakfast"

Reviewed on Jun. 13, 2024

Amsterdam Hotel
See all 970 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Westport vacation package cost?
We make it easy to see the world, with Westport packages starting from as little as CA $531. You’ll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to Westport?
Just think of all the fun things you could do in Westport with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your hotel and flights into a Westport vacation package. You have plenty of choice with Expedia too. In fact, you can pick from more than 550 airlines and 1,000,000 hotel options globally. Whether you’re taking a break with the family or traveling solo, exploring Westport is better with a package.
Where should I stay in Westport?
With popular attractions such as Compo Beach and Levitt Pavilion in this neighborhood, look for a hotel situated near either one. Westport Country Playhouse is another Westport sight that visitors flock to.
What are the top hotels in Westport?
Many people like to stay at Inn at Longshore in Greens Farms. If it’s your very first time in Westport, you’ll get a warm welcome here.
How far in advance should I book my Westport vacation?
To score discount prices, book as soon as you can. Airlines typically start selling tickets, along with some of the lowest fares, around 12 months in advance. Hotels, activities and car rental should also be booked well in advance so you can have the pick of the bunch. If you’re in need of a last-minute getaway to Westport, there are always plenty of great deals on Expedia. Book your escape today!
What does an Expedia Westport travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to create your ideal Westport travel package. Once you’ve made your booking, you can add on fun stuff like tours and experiences. Remember — the more you bundle, the more discounts you’ll get!
What should I know before booking a Westport travel package?
Whether it’s relaxation or adventure you’re chasing, a Westport vacation package lets you plan your escape your way. Plus, you’ll get access to great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Westport Expedia vacation package?
With a vacation package, you’re in control. Whether you’re eager to fly to Westport in economy or business class, simply select from the available airline options. Expedia has access to over 550 airline partners across the world.
If I'm not able to travel, can I cancel my Westport vacation package?
It’s impossible to predict what tomorrow might bring, so it’s comforting to know that you can cancel or change your Westport vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for further details.

Discover the most popular places to visit in Westport

Image for Compo Beach

Compo Beach

Why not spend a carefree afternoon at Compo Beach during your travels in Westport? Stroll along the seaside or experience the area's art scene.

Compo Beach
Image for Levitt Pavilion

Levitt Pavilion

You can make plans for a show at Levitt Pavilion during your stay in Westport. While you're in the area, stroll along the beautiful beaches.

Levitt Pavilion
Image for Westport Country Playhouse

Westport Country Playhouse

You can get tickets for a performance at Westport Country Playhouse during your stay in Westport. While you're in the area, stroll along the beautiful beaches.

Westport Country Playhouse

What to do in Westport

Image for 2-Hour Kayak Sunset Tour in Westport

2-Hour Kayak Sunset Tour in Westport

CA $115
Per adult
2-Hour Kayak Sunset Tour in Westport
See all activities in Westport

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.