Boston Vacations from $315

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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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $419, price is now $315 per person
$315
per person
Apr 16 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,418 reviews)
The staff was very responsive and respectful. The hotel itself is beautiful and very cleaned. I will be booking again during the tattoo convention

Reviewed on Mar 1, 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 $1,934, price is now $1,264 per person
$1,264
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $1,282, price is now $927 per person
$927
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (67 reviews)
Room was clean , no curtains in the bedroom area which made sleeping after the sun came up hard but the room was great .

Reviewed on Feb 26, 2026

Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was $1,195, price is now $896 per person
$896
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,604 reviews)
This place is a hidden gem! I've never experienced anything like it. I dont want to give too much away because i feel like they don't know what they have. Amazing view of downtown in an apartment type setting. This place isn't like a traditional hotel, it is my favorite place downtown.

Reviewed on Mar 5, 2026

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was $1,035, price is now $794 per person
$794
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (1,154 reviews)
The gym was nice and overall my stay was excellent

Reviewed on Mar 3, 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 Mar 22 to Mar 23
$122 total
Mar 22 - Mar 23
Total with taxes and fees
8.2/10 Very Good! (3,428 reviews)
The staff was very responsive and respectful. The hotel itself is beautiful and very cleaned. I will be booking again during the tattoo convention

Reviewed on Mar 1, 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
$159 nightly
The price is $181 total per night from Mar 21 to Mar 22
$181 total
Mar 21 - Mar 22
Total with taxes and fees
9.2/10 Wonderful! (1,962 reviews)
Beautiful Lobby, convenient to many walkable venues, restaurants and coffee shops. We walked to the Incline from here and the point park.

Reviewed on Mar 4, 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
$102 nightly
The price is $117 total per night from Mar 16 to Mar 17
$117 total
Mar 16 - Mar 17
Total with taxes and fees
8.4/10 Very Good! (1,462 reviews)
Room was clean. Staff was friendly. There was a very strong smell in the hallways but it never got in our room and didn’t affect our stay.

Reviewed on Mar 5, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,840 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 $315 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.