A river with a stone wall on one side and a wooden house with a balcony on the other.

Westport Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
  • Jan 29 - Feb 1

    Eurostars The Boxer + Flight

    West End
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,640 reviews)
    "The hotel was well maintained, staff was great. Saw a cockroach in the lobby at check in, but the hotel appeared to be clean. Great location near td garden and train station."
    Reviewed November 14, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    CA $1,085
    CA $781
    per traveller
    found 1 day ago
    Eurostars The Boxer
  • Jan 29 - Feb 1

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    CA $2,104
    CA $1,203
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • Jan 29 - Jan 31

    The Newbury Boston + Flight

    Back Bay
    2 nights
    5.0 star property
    9.4/10 - Exceptional (750 reviews)
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    Save 100% on your flight
    CA $1,380
    CA $837
    per traveller
    found 9 hours ago
    The Newbury Boston
  • Jan 29 - Feb 1

    The Langham, Boston + Flight

    Downtown Boston
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    "Amazing time - custom service was top notch We will be back"
    Reviewed November 15, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    CA $1,507
    CA $1,043
    per traveller
    found 1 day ago
    The Langham, Boston
  • Jan 29 - Jan 31

    Raffles Boston + Flight

    Back Bay
    2 nights
    5.0 star property
    9.6/10 - Exceptional (360 reviews)
    "Everything was great except the view from my room. Overlooking a carpark was not what one would expect staying with RAFFLES. Maybe paint a beautiful mural on the walls of the parking infrastructure?"
    Reviewed November 15, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,810
    CA $1,361
    per traveller
    found 2 hours ago
    Raffles Boston

Discover the most popular places to visit in Westport

Westport Hotel Deals

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.

Frequently Asked Questions

How much does a Westport vacation package cost?

You can snap up a vacation package to this top destination from CA $781 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.