Boston 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 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.
Crowne Plaza Suites Pittsburgh South by IHG

Crowne Plaza Suites Pittsburgh South by IHG

3.5 out of 5
Price was CA $1,096, price is now CA $977 per person
CA $977
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.8/10 Excellent! (1,005 reviews)
The room was very clean, but not that big, we had a room with 2 queens and it was a little tight with three adults. Staff were incredibly helpful and friendly and breakfast had a nice selection.

Reviewed on Jun 30, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $1,788, price is now CA $1,330 per person
CA $1,330
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Pittsburgh (PIT)
8/10 Very good! (298 reviews)
Only one towel and one washcloth for a two night stay. AC is evident, but rooms have no control of it. Bed was lumpy, hard and uncomfortable.

Reviewed on Jun 25, 2026

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,535, price is now CA $1,355 per person
CA $1,355
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Pittsburgh (PIT)
8.2/10 Very good! (1,259 reviews)
Spent one night there to attend a concert at PPG Arena. Hotel and Valet were all very kind.

Reviewed on Jun 30, 2026

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,580, price is now CA $1,395 per person
CA $1,395
per person
Aug 23 - Aug 27
found 1 hour ago
Roundtrip non-stop flight included
Québec (YQB) to Pittsburgh (PIT)
9.2/10 Wonderful! (2,032 reviews)
Tout est parfait Très bien situé

Reviewed on Jun 30, 2026

Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
Central Oakland
Price was CA $1,177, price is now CA $1,042 per person
CA $1,042
per person
Aug 23 - Aug 27
found 1 hour ago
Roundtrip non-stop flight included
Québec (YQB) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
It seems dated (carpeting) but clean. The biggest issue I had was there was a small yappy dog somewhere on our floor and he never shut up. I reported it to the front desk and they sent someone to check it out. Otherwise, the stay was quiet and relaxing. We walked to our appointment and we were very safe in the neighborhood. Valet was terrific taking good care of the car bringing it back abd being helpful loading the car. We have stayed here before and at checkin the clerk recognized us. That made me feel appreciated as member of the rewards p program .

Reviewed on Jun 29, 2026

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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 $190 per night from Jul 9 to Jul 10
CA $190
CA $217 total
Jul 9 - Jul 10
includes taxes & fees
8.2/10 Very good! (3,579 reviews)
"The bathroom door lock was broken. The door itself has glass panes like a shower door that aren’t 100% see through you can see through them. The mirror on the wall of the room placement is if you’re standing up by the far bed you can see in the bathroom. Odd design choices. Would still go back"

Reviewed on Jul 1, 2026

Wyndham Grand Pittsburgh Downtown
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Jul 5 to Jul 6
CA $195
CA $222 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,908 reviews)
"We got there an hour before check-in and our room was not ready until an hour after check-in."

Reviewed on Jul 1, 2026

The Landing Hotel at Rivers Casino
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
1100 Liberty Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jul 7 to Jul 8
CA $179
CA $204 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (148 reviews)
"Bobbi was amazing and I can’t wait to come back, you guys made me feel at home!"

Reviewed on Jul 1, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian
See all 1,918 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

Stay near popular Boston attractions

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.
See properties

Frequently asked questions

How much does a Boston vacation package cost?
You'll find cheap prices from CA $977 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.

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