Boston Vacations from $393

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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.
Americas Best Value Inn Pittsburgh Airport

Americas Best Value Inn Pittsburgh Airport

2 out of 5
Price was $492, price is now $393 per person
$393
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
6.6/10 (1,002 reviews)
I've stayed here a lot because it's affordable and you can get a smoking room. Usually it's not bad, you get what you pay for. This week long stay, the bed was only made twice and the floor was not swept AT ALL.

Reviewed on Jun 1, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $636, price is now $459 per person
$459
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,518 reviews)
Clean and comfortable room. Staff was friendly and knowledgeable. Nice location too:)

Reviewed on Jun 1, 2026

SpringHill Suites by Marriott Pittsburgh Bakery Square

SpringHill Suites by Marriott Pittsburgh Bakery Square

3 out of 5
Larimer
Price was $906, price is now $731 per person
$731
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Great location, good room. Good for family. Breakfast was free but very basic

Reviewed on Jun 4, 2026

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $561, price is now $457 per person
$457
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,564 reviews)
Our room was very clean and we had a nice view of the river. The shower was extremely small though and the bed was not very comfortable. The walls are quite thin so you could hear your neighbors quite well unfortunately. The pool area was quite small for a hotel that size. The hotel itself was in a great location making it easy to walk to where we wanted to go. Hotel itself is a bit on the older outdated side. Not sure if we’d stay here again.

Reviewed on Jun 2, 2026

DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was $738, price is now $601 per person
$601
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,009 reviews)
Customer experience should be prioritized over additional charges. If bottled water is not complimentary, it would be better not to place it in the room, as it can create confusion for guests. Similarly, breakfast should ideally be included in the stay, and if not, the pricing should be reasonable and provide good value. Small gestures like these go a long way in creating a positive guest experience.

Reviewed on May 30, 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
$131 nightly
The price is $150 total per night from Jun 14 to Jun 15
$150 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 $393 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.