Boston Vacations from $305

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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.
Ambridge Inn

Ambridge Inn

3 out of 5
Price was $398, price is now $305 per person
$305
per person
Feb 25 - Mar 1
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (96 reviews)
Friendly staff. Clean room

Reviewed on Nov 28, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $732, price is now $492 per person
$492
per person
Feb 25 - Mar 1
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,142 reviews)
Didn’t have breakfast but I’m sure it would’ve been delicious! Great location, walkable to everything you need from the Acrisure Stadium to area dining & shopping!

Reviewed on Jan 19, 2026

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $446, price is now $324 per person
$324
per person
Feb 25 - Mar 1
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
Staff was extremely kind, friendly and helpful! The space was clean and beautiful! The breakfast was delicious!

Reviewed on Jan 11, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $651, price is now $487 per person
$487
per person
Apr 2 - Apr 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) 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

DoubleTree by Hilton Pittsburgh - Cranberry

DoubleTree by Hilton Pittsburgh - Cranberry

4 out of 5
Price was $615, price is now $468 per person
$468
per person
Feb 25 - Mar 1
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.8/10 Excellent! (913 reviews)
Awesome and helpful front desk staff!

Reviewed on Jan 5, 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
$111 nightly
The price is $127 total per night from Feb 12 to Feb 13
$127 total
Feb 12 - Feb 13
Total with taxes and fees
8.2/10 Very Good! (3,349 reviews)
Great location. Would stay there again. Rooms very clean and well maintained facility. $44 per day for parking at hotel. You can park right around the corner in Stanewicz (sp?) for $32 per day. Have fun in the Burgh!!

Reviewed on Jan 11, 2026

Wyndham Grand Pittsburgh Downtown
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Jan 22 to Jan 23
$145 total
Jan 22 - Jan 23
Total with taxes and fees
8/10 Very Good! (1,120 reviews)
Fast courteous check in

Reviewed on Jan 18, 2026

Pittsburgh Marriott City Center
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
$159 nightly
The price is $182 total per night from Jan 22 to Jan 23
$182 total
Jan 22 - Jan 23
Total with taxes and fees
9/10 Wonderful! (1,919 reviews)
Hotel was very clean and staff was great

Reviewed on Jan 14, 2026

Omni William Penn Hotel
See all 1,782 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 $305 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.