Boston Vacations from $310

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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.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $414, price is now $310 per person
$310
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
Super clean rooms, really nice employees( front desk, bartender, server and doorman), valey parking was quick and easy.

Reviewed on Jan 24, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,726, price is now $1,096 per person
$1,096
per person
Apr 23 - Apr 27
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
7.8/10 Good! (203 reviews)
The room was clean. Just didn’t have the six bed and I didn’t have linen for my sixth guest.

Reviewed on Jan 25, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $2,100, price is now $1,448 per person
$1,448
per person
Apr 23 - Apr 27
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Kitchen was fully equipped with everything you would need. The rooms were clean and spacious, beautiful building and friendly staff. Parking is what you would expect in a downtown area but was very easy and the attendant was great.

Reviewed on Jan 14, 2026

Hilton Garden Inn Pittsburgh Airport

Hilton Garden Inn Pittsburgh Airport

3 out of 5
Save 100% on your flight
Price was $923, price is now $692 per person
$692
per person
Apr 23 - Apr 27
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9/10 Wonderful! (1,002 reviews)
Staff was great, room was clean.

Reviewed on Jan 18, 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
$107 nightly
The price is $122 total per night from Feb 12 to Feb 13
$122 total
Feb 12 - Feb 13
Total with taxes and fees
8.2/10 Very Good! (3,367 reviews)
Great location

Reviewed on Jan 20, 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
$155 nightly
The price is $177 total per night from Jan 28 to Jan 29
$177 total
Jan 28 - Jan 29
Total with taxes and fees
9/10 Wonderful! (1,929 reviews)
Room was very nice. The staff was extremely accommodating. Always stay here when in Pittsburgh.

Reviewed on Jan 22, 2026

Omni William Penn Hotel
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies Pittsburgh PA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $120 total per night from Feb 4 to Feb 5
$120 total
Feb 4 - Feb 5
Total with taxes and fees
8.4/10 Very Good! (1,424 reviews)
Clean room, friendly staff.

Reviewed on Jan 20, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,802 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 $310 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.