Two swans on a calm lake at sunset.

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

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Your Westerly Vacation

With plenty of highlights as well as some hidden gems, this city is best explored with a Westerly vacation package. Find a place to stay in Watch Hill Historic District, which is good for views, dining and shopping. If your trip to Westerly includes some sightseeing, don't miss major attractions such as Misquamicut State Beach, Watch Hill Lighthouse and The Flying Horse Carousel. Expedia is here to help you escape the everyday. Tailor your vacation to Westerly to match your travel style, whatever that may be!

Top Westerly vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Dec 11 - Dec 13

    La Quinta Inn & Suites by Wyndham Stonington-Mystic Area + Flight

    Pawcatuck
    2 nights
    3.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    Roundtrip • Toronto (YTO) - Providence (PVD)
    YYZ - BDL • 1 stop BDL - YYZ • 1 stop
    CA $1,034
    CA $966
    per traveller
    found 1 day ago
    La Quinta Inn & Suites by Wyndham Stonington-Mystic Area
  • Dec 11 - Dec 13

    Winnapaug Inn + Flight

    Westerly
    2 nights
    2.0 star property
    8.4/10 - Very good (1,003 reviews)
    Roundtrip • Toronto (YTO) - Providence (PVD)
    YYZ - BDL • 1 stop BDL - YYZ • 1 stop
    CA $1,061
    CA $979
    per traveller
    found 1 day ago
    Winnapaug Inn
  • Dec 11 - Dec 13

    Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino + Flight

    North Stonington
    2 nights
    3.5 star property
    8.6/10 - Excellent (2,730 reviews)
    Roundtrip • Toronto (YTO) - Providence (PVD)
    YYZ - BDL • 1 stop BDL - YYZ • 1 stop
    CA $1,036
    CA $968
    per traveller
    found 1 day ago
    Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino
  • Dec 11 - Dec 13

    Residence Inn by Marriott Mystic Groton + Flight

    Mystic
    2 nights
    3.0 star property
    7.8/10 - Good (28 reviews)
    "Loved the bold coffee"
    Reviewed September 20, 2026
    Roundtrip • Toronto (YTO) - Providence (PVD)
    YYZ - BDL • 1 stop BDL - YYZ • 1 stop
    CA $1,695
    CA $1,588
    per traveller
    found 1 day ago
    Residence Inn by Marriott Mystic Groton
  • Dec 11 - Dec 13

    DELAMAR MYSTIC + Flight

    Rossie Velvet Mill Historic District
    2 nights
    4.0 star property
    9.6/10 - Exceptional (18 reviews)
    Roundtrip • Toronto (YTO) - Providence (PVD)
    YYZ - BDL • 1 stop BDL - YYZ • 1 stop
    CA $1,527
    CA $1,433
    per traveller
    found 1 day ago
    DELAMAR MYSTIC

Where to stay in Westerly

Find the best Westerly areas and neighborhoods for the activities you enjoy most.

Watch Hill

You'll enjoy the beaches and waterfront in Watch Hill. You might want to make time for a stop at East Beach Watch Hill or Napatree Point.

Misquamicut

The beaches and abundant dining options are top of the list for many visitors to Misquamicut. A stop by Misquamicut State Beach or East Beach Watch Hill might round out your trip.

Watch Hill Historic District

Coastal and private, this Rhode Island gem offers bird watching at Napatree Point and landmarks like Watch Hill Lighthouse and The Flying Horse Carousel. Enjoy the growing business district near the harbor.

Weekapaug

If you're spending some time in Weekapaug, East Beach and Weekapaug Beach are top sights worth seeing.

Downtown Westerly

If you're spending some time in Downtown Westerly, Wilcox Park and Westerly Public Library are top sights worth seeing.

Discover the most popular places to visit in Westerly

What to do in Westerly

Westerly 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 Westerly vacation package cost?

You'll find cheap prices from CA $966 on Expedia for your Westerly getaway. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Westerly costs.

What are the cheapest months to go to Westerly?

You can generally find reduced prices and better availability in January, March and December. Take a look at our cheap Westerly vacation packages and you could score some great off-season deals.

How many days is enough for Westerly?

Allow at least 2 days for your Westerly vacation to enjoy everything that makes this place special. Wander around popular neighbourhoods, including Haversham and Shelter Harbour. Then check out top attractions like The Flying Horse Carousel and Saltwater Farm Vineyard. With a well-organized itinerary, you'll be kept busy with room for some downtime too. Want to venture outside of Westerly? Consider fitting in an excursion or two.

Is it worth booking a vacation package to Westerly?

It's no wonder a Westerly vacation is on the to-do list of many travellers. Top attractions like Wilcox Park are just the beginning of things to keep you busy here.

How to find the best Westerly package deals?

Bagging a cheap Westerly package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most affordable Westerly 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 Westerly vacation as a package?

An Expedia vacation package could land you considerable savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Westerly getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.

When to book a vacation package to Westerly?

If you're planning a spur-of-the-moment Westerly getaway, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking well in advance.

How to plan a trip to Westerly?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Westerly.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your hotel will likely be the largest expense during your trip to Westerly.
  3. Work out your trip length: Consider how long you'd like to spend discovering Westerly. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Westerly 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.