Boston Vacations from $516
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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.
The Latest Boston vacation packages
Price found within the past 48 hours. Click for updated prices.
Oakmont Inn
Plum
$682
per person
Dec 5 - Dec 8
found 15 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
10/10 Exceptional! (38 reviews)
From the minute we arrived to the minute we checked out, an amazing stay, very clean, beds comfortable, convenient location. Great space downstairs for family, gym, and breakfast each morning was wonderful. Will stay here again and recommend to friends and family
Reviewed on Jul 5, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
$775
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Pittsburgh (PIT)
8.6/10 Excellent! (1,004 reviews)
I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!
Reviewed on Sep 14, 2026
South Broadway Manor
$744
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Pittsburgh (PIT)
9.8/10 Exceptional! (119 reviews)
The manor was beautifully decorated and Wendy invited us to look around the whole house. Each room was unique in its interior. Next time we will stay in the carriage house, incredible accommodations! Breakfast was delicious and beds were super comfy!!!!
Reviewed on Sep 15, 2026
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.
Boston Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$124 nightly
$141 total
Oct 12 - Oct 13
Total with taxes and fees
8.4/10 Very Good! (3,797 reviews)
"No USB outlets in rooms, expensive breakfast, Hallways look old and dingy,Expensive valet, problems with wall mounted with Ac at various times, Rooms reflect older hotels from many years ago with scratched up furniture.Bright spot is best view river side of the hotel in Pittsburgh"
Reviewed on Sep 20, 2026
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$152 nightly
$173 total
Oct 16 - Oct 17
Total with taxes and fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
$149 nightly
$170 total
Oct 21 - Oct 22
Total with taxes and fees
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.
Find the Best Boston Vacation Packages
Boston Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Pittsburgh Intl. Airport (PIT) |
Population | 550 |
Top Sights | Kennywood, Sandcastle Water Park and Carnegie Museum of Natural History |
More vacations you might like
Frequently asked questions
How much does a Boston vacation package cost?
You can grab a vacation package to this top destination from $516 on Expedia. But how much your vacation to Boston costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Boston?
You can typically find reduced prices and better availability in November, December and January. Browse our cheap Boston vacation packages and you could score some great off-season deals.
How many days is enough for Boston?
Usually, a handful of days is enough to tick off the major attractions during your Boston vacation. But if you prefer to have more time to rest or go on day tours, think about extending your itinerary.
How to find the best Boston package deals?
Bagging a cheap Boston package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Boston package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Boston vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights individually. Better still, you can personalize your Boston getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Boston?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Boston vacation.
Does Expedia offer Book Now, Pay Later Boston vacation packages?
If you're like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Boston trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
