Boston Vacations from $252

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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.
Cadiz Motel by OYO on route 250

Cadiz Motel by OYO on route 250

2.5 out of 5
Price was $314, price is now $252 per person
$252
per person
Aug 5 - Aug 8
found 1 hour ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
9/10 Wonderful! (83 reviews)
Beds were comfortable. Need instructions to get there. No complimentary breakfast. Water was to be boiled before using. Supplied water. Was an older motel.

Reviewed on Aug 7, 2025

Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
Central Oakland
Price was $1,109, price is now $806 per person
$806
per person
Aug 1 - Aug 8
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
My daughter has to go to Montefiore hospital and this hotel is in walking distance. You can still drive as well. Also, there are many restaurants in walking distance.

Reviewed on Jun 19, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $786, price is now $625 per person
$625
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8/10 Very Good! (293 reviews)
There's no receptionist on site will need communicate with an answering service to obtain entry code for the hotel. Also no onsite parking. I spent more money than I wished to.

Reviewed on Jun 16, 2026

Traveler's Rest Hotel

Traveler's Rest Hotel

2 out of 5
South Side Flats
Price was $628, price is now $506 per person
$506
per person
Jul 26 - Jul 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9.6/10 Exceptional! (104 reviews)
It was a realy cool place and I would definitely recommend it . Friendly, cozy and definitely differant but an awsome experience.

Reviewed on Jun 9, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $704, price is now $580 per person
$580
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.4/10 Very Good! (127 reviews)
The location was great. I was in town for Graduation at Carnegie Mellon and it was a great place to stay and it had paid parking which was useful for us. The premises were very clean and inviting and we enjoyed our stay in the place.

Reviewed on Jun 19, 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 Jul 19 to Jul 20
$127 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (3,581 reviews)
"Helpful staff"

Reviewed on Jun 20, 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
$126 nightly
The price is $144 total per night from Jun 29 to Jun 30
$144 total
Jun 29 - Jun 30
Total with taxes and fees
9.4/10 Exceptional! (1,866 reviews)
"Very clean and tidy room."

Reviewed on Jun 20, 2026

The Landing Hotel at Rivers Casino
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
$118 nightly
The price is $135 total per night from Jul 19 to Jul 20
$135 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,263 reviews)
"The staff were very accommodating and helpful."

Reviewed on Jun 20, 2026

Pittsburgh Marriott City Center
See all 1,916 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 $252 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.