Boston Vacations from $340

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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.
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was $429, price is now $340 per person
$340
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (1,058 reviews)
Perfect place to stay downtown !! Walking distance to everything! Wonderful staff! Highly recommend!

Reviewed on May 5, 2026

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $759, price is now $473 per person
$473
per person
Jun 12 - Jun 15
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,506 reviews)
Room was run down/old. Shower head was coming out of the wall and couldnt get the water hot. The phone in the room was making a loud buzzing noise so I just disconnected the cord. Rest of venue and area was super.l, staff was friendly. Room was clean. Easy access.to a late.checkout that was needed.

Reviewed on May 6, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $671, price is now $517 per person
$517
per person
Jul 14 - Jul 18
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8.4/10 Very Good! (97 reviews)
Pros: cRoom was clean and nice size. Kitchen had everything we have it at home except for food. Bed was very comfortable. Staff and valet were very helpful. We arrived to town early and were checked in at 1pm which was nice, because we wanted to walk to the NFL draft. Cons: one side of the hotel is next to train tracks, Friday night we counted four trains and could hear the trains loud and clear. We counted 4 trains pass by our room between 11 PM and 3:30 AM, so we didn’t sleep most of the night. The hotel has virtually no amenities, no restaurant, and no free breakfast.

Reviewed on Apr 26, 2026

Crowne Plaza Suites Pittsburgh South by IHG

Crowne Plaza Suites Pittsburgh South by IHG

3.5 out of 5
Price was $670, price is now $522 per person
$522
per person
Jul 14 - Jul 18
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
The stay was perfect.

Reviewed on May 6, 2026

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
Oakland
Price was $977, price is now $780 per person
$780
per person
Jul 14 - Jul 18
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
9/10 Wonderful! (692 reviews)
Menu could use more variety

Reviewed on May 2, 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
$161 nightly
The price is $184 total per night from Jun 7 to Jun 8
$184 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (3,532 reviews)
Room was run down/old. Shower head was coming out of the wall and couldnt get the water hot. The phone in the room was making a loud buzzing noise so I just disconnected the cord. Rest of venue and area was super.l, staff was friendly. Room was clean. Easy access.to a late.checkout that was ...

Reviewed on May 6, 2026

Wyndham Grand Pittsburgh Downtown
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
$219 nightly
The price is $250 total per night from May 10 to May 11
$250 total
May 10 - May 11
Total with taxes and fees
9.2/10 Wonderful! (2,003 reviews)
Staff were nice and the rooms are clean.

Reviewed on May 5, 2026

Omni William Penn Hotel
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 May 10 to May 11
$154 total
May 10 - May 11
Total with taxes and fees
9.4/10 Exceptional! (1,683 reviews)
Not many breakfast options

Reviewed on May 6, 2026

The Landing Hotel at Rivers Casino
See all 1,945 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 $340 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.