Boston Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith 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.
DoubleTree by Hilton Pittsburgh - Green Tree
CA $1,196
per person
Nov 13 - Nov 16
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,236 reviews)
Such a lovely hotel. So close to everything. Rooms were spotless, staff were friendly, parking was abundant, and always felt safe as mother traveling with small children. When we go back to Pittsburgh this is where we will stay.
Reviewed on Oct 6, 2026
The Inn on Negley
Shadyside
CA $1,285
per person
Nov 13 - Nov 16
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
10/10 Exceptional! (225 reviews)
This Inn is beautiful, perfectly located within a couple minutes of downtown, very well maintained, breakfast was wonderful, the room was super comfortable with quality linens and a very comfortable batch. Wonderful staff as well, Peter gave us some history of Pittsburgh and some ideas to make our trip back home even better! We plan on coming back to Pittsburgh and staying here again.
Reviewed on Sep 30, 2026
Ready to book your vacation to Boston?
Boston Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $176
CA $201 total
Oct 22 - Oct 23
includes taxes & fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $191
CA $218 total
Oct 18 - Oct 19
includes taxes & fees
DoubleTree by Hilton Pittsburgh - Green Tree
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $155
CA $177 total
Nov 3 - Nov 4
includes taxes & fees
8.8/10 Excellent! (1,250 reviews)
"Such a lovely hotel. So close to everything. Rooms were spotless, staff were friendly, parking was abundant, and always felt safe as mother traveling with small children. When we go back to Pittsburgh this is where we will stay."
Reviewed on Oct 6, 2026
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.
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.
Frequently asked questions
How much does a Boston vacation package cost?
You'll find cheap prices from CA $947 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?
- 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.
- 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.
- 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.
- 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.
