Westport Vacation Packages

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Your Westport Vacation

Lock in a Westport vacation package and get set for an awesome adventure. Famous for its coastal scenery and spectacular views, there's loads to love about this captivating city. A trip to Westport is a great opportunity to do a bit of sightseeing. Make sure you visit popular attractions like Horseneck State Beach, Coastal Vineyards and Gooseberry Island. Whatever your travel plans or the size of your budget, organizing a tailored Westport vacation is easy with Expedia.

Top Westport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,008, price is now CA $536 per person
CA $536
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Price was CA $2,417, price is now CA $1,572 per person
CA $1,572
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (139 reviews)
Clean. Great location.

Reviewed on Jul. 31, 2025

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2 out of 5
South End
Price was CA $2,281, price is now CA $1,491 per person
CA $1,491
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (118 reviews)
Property is located in a very nice area. No frill, what they advertise, you get.

Reviewed on May 23, 2025

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

2 out of 5
Coolidge Corner South Side
Price was CA $1,950, price is now CA $1,289 per person
CA $1,289
per person
Oct 25 - Nov 1
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (247 reviews)
We stayed here for a few days while visiting Boston, once at the beginning of our trip and once at the end and found it very convenient to hop on the train and walk to lots of shops and restaurants. The first room was on the third floor and was very small but was fine for two people. It was clean and had everything we needed. Our second room was in the basement and much larger and again, very clean and well-appointed. We did have some noise from the room above us but it wasn't a big issue. They provide earplugs in each room which was great. I will plan to stay here again the next time I am in town visiting and would recommend this location for anyone staying in Brookline.

Reviewed on Jul. 16, 2025

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,563, price is now CA $1,038 per person
CA $1,038
per person
Oct 5 - Oct 10
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
Phil’s property is immaculate and the rooms are very clean and will all required amenities. Phil’s hospitality is also top notch and it will be my place to stay in my future cape cod visits!!

Reviewed on Aug. 20, 2025

Westport Beach Vacation

Shake off life's daily stresses and let your body, mind and soul unwind on your Westport vacation. Few things are more invigorating than the cool sea breeze and the soothing rhythm of waves breaking onto the shore. Plan your trip to Westport the easy way by choosing one of our Westport packages. Many visitors opt to spend their nights near Horseneck Beach State Reservation, a local highlight only 8 kilometres from the downtown area.

Things You Should Know About Westport

Ready to book your vacation to Westport?

 

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Westport Hotel Deals

Hampton Inn Fall River/Westport

Hampton Inn Fall River/Westport

2.5 out of 5
53 Old Bedford Rd, Westport, MA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Sep 3 to Sep 4
CA $199
CA $218 total
Sep 3 - Sep 4
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"I liked that the room was spacious and quiet. I had booked a suite and the bed as well as the sofa bed were comfortable. The breakfast was fine except for the use of paper plates and plasticware. It would be better to have real plates and silverware."

Reviewed on Aug. 18, 2025

Hampton Inn Fall River/Westport
The Newport Harbor Hotel & Marina

The Newport Harbor Hotel & Marina

3 out of 5
49 America's Cup Ave, Newport, RI
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Sep 1 to Sep 2
CA $248
CA $336 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (1,219 reviews)
"Great location. Beautiful views of the harbor, very close to shops and restaurants. 10 minute walk to free hop on hop off shuttle to the Newport Mansions. Nice restaurant/bar onsite."

Reviewed on Aug. 21, 2025

The Newport Harbor Hotel & Marina
Omni Providence Hotel

Omni Providence Hotel

4 out of 5
1 W Exchange St, Providence, RI
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Sep 7 to Sep 8
CA $219
CA $252 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (2,689 reviews)
"Lovely stay!"

Reviewed on Aug. 21, 2025

Omni Providence Hotel
See all 3,104 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

Discover the most popular places to visit in Westport

Horseneck State Beach

If a restful vacation is part of your travel plans, Horseneck State Beach might be the perfect place to seek out during your trip to Westport. Wander the riverfront in this family-friendly area.

Horseneck State Beach

Westport Rivers Vineyard & Winery

You can enjoy a tasting or tour at Westport Rivers Vineyard & Winery during your travels to Westport. Stroll along this family-friendly area's riverfront, or simply enjoy its wineries.

Westport Rivers Vineyard & Winery

Frequently asked questions

How much does a Westport vacation package cost?
You can snap up a vacation package to this top destination from CA $536 on Expedia. However, how much your vacation to Westport costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Westport?
January, February and March are the best times to look for cheap Westport vacation packages. Travelling in less busy months means you can typically find better prices on flights and hotels.
How many days is enough for Westport?
Usually, a handful of days is enough to visit the main attractions during your Westport vacation. However, if you prefer to have some time to unwind or go on day tours, consider extending your itinerary.
Is it worth booking a vacation package to Westport?
It's easy to see why a Westport vacation is on the to-do list of many travellers. Top attractions like Acoaxet Club are just the beginning of what you can explore here.
How to find the best Westport package deals?
Finding a cheap Westport package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Westport package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Westport vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component individually. And you'll still get the freedom to create a tailored Westport vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Westport?
If you've got your Westport travel dates confirmed, book as soon as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Westport?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Westport.
  2. Calculate your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your accommodations will probably be the biggest expense during your trip to Westport.
  3. Decide your trip length: Consider how long you want to spend discovering Westport. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Westport vacation package that brings all your bookings together.

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