Boston Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Your Boston Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Boston vacation package. Check out places to stay in Squirrel Hill South, which is great for cycling, golfing and dining. A trip to Boston is a superb opportunity to do a bit of sightseeing. Make sure you visit well-known attractions like Kennywood, McKeesport Little Theater and Round Hill Park. Don't put off your visit to this destination any longer. The ultimate Boston vacation is a few quick clicks away with Expedia.

Top Boston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $962, price is now CA $754 per person
CA $754
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
7.8/10 Good! (169 reviews)
Only a couple of visible stains, nothing out of the ordinary. Very convenient hotel booking with affordable rates. Support was very responsive to questions. Would absolutely stay again.

Reviewed on Aug. 26, 2025

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was CA $2,031, price is now CA $1,554 per person
CA $1,554
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Our toilet was clogged and we were right next to the elevators

Reviewed on Aug. 26, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $1,813, price is now CA $1,401 per person
CA $1,401
per person
Oct 3 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
7.6/10 Good! (16 reviews)
Unique, incredible preservation of the historical aspects of the property fused with modern design in the condos .

Reviewed on Aug. 25, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $1,887, price is now CA $1,465 per person
CA $1,465
per person
Oct 3 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Everything was great

Reviewed on Aug. 12, 2025

Springhill Suites by Marriott Pittsburgh Mt. Lebanon

Springhill Suites by Marriott Pittsburgh Mt. Lebanon

2 out of 5
Mount Lebanon
Price was CA $1,318, price is now CA $1,030 per person
CA $1,030
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (760 reviews)
The room was very spacious and well appointed. The property itself was conveniently located to everything. The staff was very eager to provide information and directions. I am definitely staying at this property upon my return visit Pittsburgh.

Reviewed on Aug. 25, 2025

Ready to book your vacation to Boston?

 

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Boston Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Aug 28 to Aug 29
CA $210
CA $240 total
Aug 28 - Aug 29
includes taxes & fees
8/10 Very Good! (2,990 reviews)
"."

Reviewed on Aug. 25, 2025

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Sep 10 to Sep 11
CA $220
CA $251 total
Sep 10 - Sep 11
includes taxes & fees
Omni William Penn Hotel
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Sep 7 to Sep 8
CA $163
CA $190 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (1,341 reviews)

Reviewed on Aug. 21, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,693 properties in Boston
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 Boston

Northeast Paddleboard Company

Take the family on an outing to Northeast Paddleboard Company during your trip to Boston. Amble around the area's riverfront or attend a sporting event.

Northeast Paddleboard Company

Frequently asked questions

How much does a Boston vacation package cost?
You'll find cheap prices from CA $754 on Expedia for your Boston break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Boston costs.
What are the cheapest months to go to Boston?
You're likely to find lower prices and greater availability in January, February and March. Browse our cheap Boston vacation packages and you could land some great off-season deals.
How many days is enough for Boston?
Dedicate around 2 days for your Boston vacation if you want to enjoy all that makes this place special. Stroll around key areas, including Versailles and Dravosburg. Then check out major sights such as Grand Theatre and Round Hill Park. With a well-organized itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Boston? Consider squeezing in an excursion or two.
How to find the best Boston package deals?
Finding a cheap Boston package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Boston package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Boston vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a customized Boston vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Boston?
If you're planning a spur-of-the-moment Boston vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Boston?

  1. Choose when to go: Check your diary and get packing. Your preferred time of year and the available activities will also help you decide when to visit Boston.
  2. Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will likely be the largest expense during your trip to Boston.
  3. Decide how long to go away for: Now that you're more familiar with Boston, you can figure out the ideal length of your vacation. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Boston vacation package.

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