Boston Vacations from $614

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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.
The Carriage House Inn Bed and Breakfast

The Carriage House Inn Bed and Breakfast

3 out of 5
Price was $792, price is now $614 per person
$614
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
10/10 Exceptional! (24 reviews)

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $949, price is now $644 per person
$644
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (313 reviews)
Very responsive, great location, awesome hosts! 10/10 would recommend.

Reviewed on Jul 31, 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 $1,849, price is now $1,310 per person
$1,310
per person
Oct 14 - Oct 18
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
The staff at the Westin was extremely helpful and proactive. The initial room they gave us had some issues, including a smoke-like smell (not cigarette smoke). As soon as we notified reception, someone handled it extremely professionally, and within minutes we were moved to a much better room.

Reviewed on Aug 3, 2026

The Maverick by Kasa

The Maverick by Kasa

3 out of 5
East Liberty
Price was $856, price is now $673 per person
$673
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
9/10 Wonderful! (1,011 reviews)

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $1,024, price is now $820 per person
$820
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,583 reviews)
The room was very clean and the bed was very comfortable

Reviewed on Aug 4, 2026

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Stay near popular Boston attractions

Northeast Paddleboard Company

Take the family on an outing to Northeast Paddleboard Company during your trip to Boston. Amble around the area's riverfront or attend a sporting event.
See properties

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 Sep 1 to Sep 2
$141 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (3,711 reviews)
"Great location. Friendly staff. We will stay again."

Reviewed on Aug 5, 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
$135 nightly
The price is $154 total per night from Aug 23 to Aug 24
$154 total
Aug 23 - Aug 24
Total with taxes and fees
9.4/10 Exceptional! (2,113 reviews)
"Stayed here many times. Never disappoints"

Reviewed on Aug 5, 2026

The Landing Hotel at Rivers Casino
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
$179 nightly
The price is $204 total per night from Aug 9 to Aug 10
$204 total
Aug 9 - Aug 10
Total with taxes and fees
Omni William Penn Hotel
See all 1,924 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 $614 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.