Boston Vacations from $438

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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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Stay Pittsburgh
Hilton Garden Inn Pittsburgh University Place
461 Melwood Suites Unit 102  Studio
The Westin Pittsburgh, a Marriott Hotel
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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
$125 nightly
The price is $142 total per night from Jun 21 to Jun 22
$142 total
Jun 21 - Jun 22
Total with taxes and fees
8.2/10 Very Good! (3,588 reviews)
"Room was small, thermostat wasn’t working right, no valet parking available, over priced"

Reviewed on Jun 7, 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
$135 nightly
The price is $154 total per night from Jun 14 to Jun 15
$154 total
Jun 14 - Jun 15
Total with taxes and fees
9.4/10 Exceptional! (1,797 reviews)
"Very clean and nice hotel. We made a mistake and booked the wrong nights so when we showed up a day late they said they cancelled both nights we had paid for and hotel staff were unwilling to help us or give any sort of refund because we had booked with hotels.com, said hotels.com could do it but ..."

Reviewed on Jun 6, 2026

The Landing Hotel at Rivers Casino
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $203 total per night from Jun 14 to Jun 15
$203 total
Jun 14 - Jun 15
Total with taxes and fees
9.2/10 Wonderful! (2,018 reviews)
"This gorgeous classic hotel in the heart of Pittsburgh is an easy walk to anywhere in the downtown area, the North Shore including PNC park and the Warhol Museum, and to the South Shore's Station Square area and the lower Monongahela incline. Our room was clean and comfortable and the staff was helpful. ..."

Reviewed on Jun 6, 2026

Omni William Penn Hotel
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

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Frequently asked questions

How much does a Boston vacation package cost?
You can grab a vacation package to this top destination from $438 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.