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
- Rest easyPlan, book, and manage your trip all in one place
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.
Etage Executive Living
Downtown Pittsburgh
CA $1,651
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,909 reviews)
Checkin was quick, room was ready. Rooms are large and should be great for most stays. However, the room wasn’t really maintained well and definitely hadn’t been cleaned recently. There was a LOT of dust and dirt on the floor, the fume hood over the stove, the main hallway too. 2 TV’s in the room and neither worked. One came on, but the remote wouldn’t work. The other had a cable just hanging from it on the wall. I found the xfinity box it was supposed to connect to, connected it…that remote didn’t work either. Pull-out bed had no linens, so I had to ask and wait for those. The pillows for the pull out had what looked like dried blood on one of them…so they weren’t used. The fridge smelled like garlic. The smooth cooktop had baked on crud around 2 of the burners. When we checked out, they didn’t even ask how our stay was. Worse yet, we sat in the lobby for a few mins as my wife went to grab a coffee around the corner. My daughter was with us, having a broken foot and being on crutches, we sat in the lobby to wait before departure. One of the cleaning staff asked how long we’d be sitting there, as she had to mop the floor and we were in her way. Potential to be fantastic, but let down by poor maintenance and rude or uncaring staff.
Reviewed on Oct 1, 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
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $217
CA $247 total
Oct 16 - Oct 17
includes taxes & fees
8.2/10 Very good! (1,332 reviews)
"Staff at the front desk were amazing. So friendly!"
Reviewed on Oct 1, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
CA $186
CA $213 total
Oct 6 - Oct 7
includes taxes & fees
9.4/10 Exceptional! (2,383 reviews)
"No coffee maker or microwave in room."
Reviewed on Oct 1, 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 $1,059 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.
