Boston Vacations from $345

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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.
Davis Motel

Davis Motel

2 out of 5
Price was $430, price is now $345 per person
$345
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Pittsburgh (PIT)
8.6/10 Excellent! (833 reviews)
Staff were excellent. Room was very clean. It is an older motel. No complaints.

Reviewed on May 22, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $721, price is now $513 per person
$513
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (287 reviews)
The unit was more thsn adequate, clean, well equipped, and quiet. Great place and great value.

Reviewed on Jun 4, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $552, price is now $420 per person
$420
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,518 reviews)
I havnt slept that good in a while , right when I woke up I lifted the sheets to see what brand mattress and pillows they were. 100 out of 10

Reviewed on Jun 5, 2026

The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
Oakland
Save 100% on your flight
Price was $1,278, price is now $1,024 per person
$1,024
per person
Jul 28 - Aug 3
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
9.2/10 Wonderful! (780 reviews)
Great!!! John, the concierge was incredible!!! Thanks

Reviewed on Jun 1, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $570, price is now $458 per person
$458
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (112 reviews)
good location, perfect for family travel

Reviewed on Jun 3, 2026

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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 30 to Jul 1
$142 total
Jun 30 - Jul 1
Total with taxes and fees
8.2/10 Very Good! (3,576 reviews)
"very nice hotel. there are extra fees for parking."

Reviewed on Jun 3, 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! (1,787 reviews)
"Great"

Reviewed on Jun 4, 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
$189 nightly
The price is $215 total per night from Jun 7 to Jun 8
$215 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (2,011 reviews)
"Staff amazing. Room spacious"

Reviewed on Jun 4, 2026

Omni William Penn Hotel
See all 1,925 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.

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 $345 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.