Boston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • 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

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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.
Hyatt Regency Pittsburgh International Airport

Hyatt Regency Pittsburgh International Airport

3.5 out of 5
Price was CA $1,396, price is now CA $1,163 per person
CA $1,163
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,793 reviews)
We stayed one night since we had an early flight. The hotel is clean and has all the amenities but was the loudest hotel we have stayed in. There was noise from the rooms around and above us and from the hallway. We also were woken up at 4am by some loud vibrations within the wall. No one could have slept through the noise. When we brought it to their attention, they apologized but that didn’t help with our sleepless night before a long day of travel. We would stay again only if absolutely necessary.

Reviewed on Nov 14, 2026

Villagio Boutique Hotel

Villagio Boutique Hotel

4 out of 5
North Side
Price was CA $1,621, price is now CA $1,194 per person
CA $1,194
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9.4/10 Exceptional! (175 reviews)

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $1,812, price is now CA $1,445 per person
CA $1,445
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)

The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
Oakland
Price was CA $1,679, price is now CA $1,352 per person
CA $1,352
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9.2/10 Wonderful! (846 reviews)
Great stay at the Oaklander! Convenient location while visiting our son at Pitt. Friendly staff, clean rooms, will come again!

Reviewed on Nov 15, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,533, price is now CA $1,264 per person
CA $1,264
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
great

Reviewed on Nov 14, 2026

Ready to book your vacation to Boston?

 

Choose your dates

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 $176 per night from Nov 30 to Dec 1
CA $176
CA $201 total
Nov 30 - Dec 1
includes taxes & fees
8.4/10 Very good! (3,913 reviews)
"Rooms themselves are small and show their age, clean and functional though. Staff was very helpful...even during a busy convention. My coffee maker didn't work so they dropped off a new one quickly."

Reviewed on Nov 15, 2026

Wyndham Grand Pittsburgh Downtown
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Dec 16 to Dec 17
CA $154
CA $176 total
Dec 16 - Dec 17
includes taxes & fees
DoubleTree by Hilton Pittsburgh - Green Tree
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 $196 per night from Nov 24 to Nov 25
CA $196
CA $223 total
Nov 24 - Nov 25
includes taxes & fees
9.4/10 Exceptional! (2,578 reviews)
"Perfect spot if you’re going to a game! Walkable, parking is included in the rate, which was a huge plus, breakfast was great with lots of options"

Reviewed on Nov 15, 2026

The Landing Hotel at Rivers Casino
See all 1,795 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 $1,163 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.