A calm sea with a sandy beach and a distant landmass under a partly cloudy sky.

Wareham Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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Your Wareham Vacation

The rich history and coastal scenery are just the start of the things Wareham has on offer. Experience the sights and sounds of this lively city your way with a personalized Wareham vacation package. You'll want to do some exploring during your trip to Wareham. Carve out some time for big-name attractions such as Onset Beach, Swifts Beach and Myles Standish State Forest. No matter your travel plans or budget, putting together the ultimate tailored Wareham vacation is a breeze with Expedia.

Top Wareham vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 29 - Feb 1

    Boston Lodge and Suites + Flight

    Dorchester
    3 nights
    4.0 star property
    8.4/10 - Very good (194 reviews)
    "The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
    Reviewed October 17, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,412
    CA $707
    per traveller
    found 1 day ago
    Boston Lodge and Suites
  • Jan 29 - Jan 31

    Boston Harbor Hotel + Flight

    North End
    2 nights
    5.0 star property
    9.8/10 - Exceptional (1,006 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    CA $1,530
    CA $963
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • Jan 29 - Feb 1

    Four Seasons Hotel Boston + Flight

    Bay Village
    3 nights
    5.0 star property
    9.4/10 - Exceptional (496 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YYZ • Nonstop
    CA $2,397
    CA $1,548
    per traveller
    found 1 day ago
    Four Seasons Hotel Boston
  • Jan 14 - Jan 17

    Raffles Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.6/10 - Exceptional (354 reviews)
    "Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    Save 100% on your flight
    CA $2,235
    CA $1,488
    per traveller
    found 1 day ago
    Raffles Boston
  • Jan 14 - Jan 17

    The Newbury Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.4/10 - Exceptional (747 reviews)
    "Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    Save 100% on your flight
    CA $1,789
    CA $1,298
    per traveller
    found 1 day ago
    The Newbury Boston

Discover the most popular places to visit in Wareham

Wareham 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 Wareham vacation package cost?

You can grab a vacation package to this top destination from CA $707 on Expedia. But how much your vacation to Wareham costs will depend on your hotel choice, length of stay and season.

What are the cheapest months to go to Wareham?

January, February and March are great times to search for cheap Wareham vacation packages. Choosing to travel in quieter months means you can typically find reduced prices on accommodations and flights.

How many days is enough for Wareham?

You can easily see all the leading sights in Wareham in a few days, including the popular Myles Standish State Forest. If you're looking for a longer Wareham vacation, check out what sort of excursions and activities are available in the area.

How to find the best Wareham package deals?

Start your search for a Wareham package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Wareham package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Wareham escape off to a flying start.

Is it cheaper to book a Wareham vacation as a package?

You can enjoy significant savings on your next Wareham getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Wareham?

If you have your Wareham travel dates confirmed, book as soon as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for setting off on a whim.

How to plan a trip to Wareham?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Wareham.
  2. Budget wisely: On top of the cost of your hotel, you should consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Wareham.
  3. Decide how long to go for: Now that you're more familiar with Wareham, you can work out the ideal length of your vacation. Put together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Wareham vacation package.

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