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.
Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
per person
Jul. 8 - Jul. 12
Roundtrip non-stop flight included
Québec (YQB) to White Plains (HPN)
7.8/10 Good! (1,001 reviews)
The Hotel NoMa, Trademark Collection by Wyndham is clean and convenient. The bed was very comfortable. The breakfast I had at the hotel restaurant was plentiful and delicious. Two complaints: 1) The bathroom floors and bathtub/shower are VERY slippery and potentially unsafe. There is no bath mat available. 2) There is a $15.00 per day “Boutique Fee”, which is not mentioned anywhere on the Expedia.com listing for the hotel. When I asked what it was for, I was told it was for amenities such as parking. However, on the Expedia.com listing for the Hotel NoMa, Trademark Collection by Wyndham, it states, “Parking Included”.

Reviewed on May 21, 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
Jun. 28 - Jul. 1
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
No reviews
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
per person
Jul. 29 - Aug. 3
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.4/10 Very Good! (1,078 reviews)
my shower drain clogged

Reviewed on May 19, 2024

The Stamford Hotel

The Stamford Hotel

3.5 out of 5
Downtown Stamford
per person
Aug. 14 - Aug. 17
Roundtrip flight included
Québec (YQB) to White Plains (HPN)
7.8/10 Good! (1,085 reviews)
First off the staff was AMAZING from check in to check out. 3 girls at check in were so great with my family. Lady with dual citizenship beyond friendly and helpful! Lady with mask was super nice and help with parking for making us “wait”. It was not long at all in my opinion despite a tired kid. The other kind lady hooked us up with a special off the menu from the kitchen for the kids! Bartender Mo also took great care of us. Pizza is as advertised and fantastic! Rooms and facilities were great. Can’t say enough about this place. We will be back next time through! Thank you!

Reviewed on May 22, 2024

The Armon Hotel & Conference

The Armon Hotel & Conference

3 out of 5
per person
Jul. 8 - Jul. 12
Roundtrip flight included
Montreal (YUL) to White Plains (HPN)
7.6/10 Good! (153 reviews)
Easy and prompt check in and out. The hotel has an excelent location. It is very close to dinning and shopping options. It is a little dated, but is clean and comfortable. We'll stay here again.

Reviewed on May 8, 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 $242 per night from May 27 to May 28
CA $242
CA $279 total
includes taxes & fees
May 27 - May 28
9/10 Wonderful! (107 reviews)
"Lovely"

Reviewed on May 13, 2024

Inn at Longshore
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
The price is CA $136 per night from May 26 to May 27
CA $136
CA $158 total
includes taxes & fees
May 26 - May 27
8.4/10 Very Good! (1,505 reviews)
"Relatively old but clean, safe and quiet."

Reviewed on May 20, 2024

Amsterdam Hotel
The Circle Hotel Fairfield
The Circle Hotel Fairfield
3 out of 5
417 Post Road, Fairfield, CT
The price is CA $173 per night from May 27 to May 28
CA $173
CA $198 total
includes taxes & fees
May 27 - May 28
8.8/10 Excellent! (1,089 reviews)
"Room was spotless as was the bath. Decor is rather stark, light fixtures have too much glare(no shades) and Roku tv sucks. Id much rather watch local stations than 1 day or 1 hour old news from Detroit."

Reviewed on May 16, 2024

The Circle Hotel Fairfield
See all 977 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.

Explore other types of vacation packages

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 $772. 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
Image for Bridgeport Scavenger Hunt: Connecticut's Biggest Sights

Bridgeport Scavenger Hunt: Connecticut's Biggest Sights

CA $17
Per adult
Bridgeport Scavenger Hunt: Connecticut's Biggest Sights
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.