Boston Vacations from $478

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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
Save 100% on your flight
Price was $707, price is now $478 per person
$478
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
6.6/10 (1,002 reviews)
In the room, under the chair was dirty clothing left behind by someone else. No coffee pot in room. Facility is nice, the room was otherwise nice, staff were super friendly.

Reviewed on Jun 13, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,111, price is now $660 per person
$660
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,527 reviews)
Nothing stood out about this hotel. I would not stay here again. The room was very small and if there are amenities we didn’t know about them.

Reviewed on Jun 14, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $931, price is now $581 per person
$581
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
8/10 Very Good! (290 reviews)
Third time staying at the property. Minor issue with the elevator being out of service for a couple of days, but otherwise another pleasant stay. Will definitely be back when I’m in the area.

Reviewed on Jun 14, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $2,046, price is now $1,375 per person
$1,375
per person
Aug 27 - Sep 3
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
It’s a nice hotel with friendly staff. I think you should give a discount or free parking for people staying at the hotel. The cost to parks adds up quick.

Reviewed on Apr 10, 2026

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Save 100% on your flight
Price was $733, price is now $540 per person
$540
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
8/10 Very Good! (1,000 reviews)
This hotel is beautiful. I will be back again.

Reviewed on Jun 11, 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
$124 nightly
The price is $141 total per night from Jul 9 to Jul 10
$141 total
Jul 9 - Jul 10
Total with taxes and fees
8.2/10 Very Good! (3,639 reviews)
"Great stay."

Reviewed on Jun 14, 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
$174 nightly
The price is $198 total per night from Jun 29 to Jun 30
$198 total
Jun 29 - Jun 30
Total with taxes and fees
9.2/10 Wonderful! (2,035 reviews)
"Helpful staff and great location."

Reviewed on Jun 14, 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
$129 nightly
The price is $147 total per night from Jun 30 to Jul 1
$147 total
Jun 30 - Jul 1
Total with taxes and fees
9.4/10 Exceptional! (1,831 reviews)
"The breakfast wasnt good pancakes were hard."

Reviewed on Jun 14, 2026

The Landing Hotel at Rivers Casino
See all 1,918 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 $478 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.