Boston Vacations from $580

Book a Hotel + Flight or Car together to unlock savings

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.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $805, price is now $580 per person
$580
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
7.8/10 Good! (203 reviews)
Very responsive and right in the heart of downtown Pgh

Reviewed on Nov 23, 2025

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 $1,039, price is now $728 per person
$728
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
All is well except for the communication. You can rarely get a hold of anybody at the front desk.

Reviewed on Nov 15, 2025

Renaissance Pittsburgh Hotel

Renaissance Pittsburgh Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,371, price is now $984 per person
$984
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
9/10 Wonderful! (1,001 reviews)
Greatest thing was location, next best thing was staff, very friendly and accommodating. The room was clean enough but we were short on towels a couple times and the hotel is getting somewhat older

Reviewed on Nov 22, 2025

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
North Shore
Save 100% on your flight
Price was $1,179, price is now $868 per person
$868
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8.6/10 Excellent! (1,318 reviews)
Good location for our needs, but they did not warn visitors of street closure for 10 mile race which blocked in cars until 10:30 am

Reviewed on Nov 20, 2025

Seven Springs Resort Properties

Seven Springs Resort Properties

4.5 out of 5
Price was $1,186, price is now $882 per person
$882
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Pittsburgh (PIT)
8.4/10 Very Good! (23 reviews)
The resort is amazing. The condo was very dated and had a lot of wear and tear. It didn't diminish our trip but could use updates and repairs.

Reviewed on Oct 1, 2025

Don't see what you're looking for?
See all available trips from Columbus to Boston
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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
$108 nightly
The price is $123 total per night from Dec 16 to Dec 17
$123 total
Dec 16 - Dec 17
Total with taxes and fees
8/10 Very Good! (3,208 reviews)
Friendly staff and great location! If needed, there’s public parking across the street, daily rates apply, but very convenient.

Reviewed on Nov 24, 2025

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
$163 nightly
The price is $186 total per night from Dec 12 to Dec 13
$186 total
Dec 12 - Dec 13
Total with taxes and fees
9/10 Wonderful! (1,791 reviews)
The spout on the bathtub was broken and the deposit costs were way too high. However the staff was very friendly and helpful. Everything costs extra though and is way over priced.

Reviewed on Nov 24, 2025

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
$99 nightly
The price is $113 total per night from Dec 4 to Dec 5
$113 total
Dec 4 - Dec 5
Total with taxes and fees
8.4/10 Very Good! (1,393 reviews)
Good times

Reviewed on Nov 21, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,753 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Boston vacation package cost?
You can grab a vacation package to this top destination from $580 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.