Boston Vacations

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Find the Best Boston Vacation Packages

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
The price is AED 545 per night from Jun 16 to Jun 17
AED 545
AED 622 total
16 Jun - 17 Jun
includes taxes & fees
8/10 Very Good! (2,877 reviews)
"Was very disappointed that valet and parking was not avail"

Reviewed on 3 June 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
The price is AED 585 per night from Jun 22 to Jun 23
AED 585
AED 667 total
22 Jun - 23 Jun
includes taxes & fees
9/10 Wonderful! (1,487 reviews)
"Always a pleasant place to stay."

Reviewed on 5 June 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
The price is AED 465 per night from Jun 15 to Jun 16
AED 465
AED 530 total
15 Jun - 16 Jun
includes taxes & fees
8.2/10 Very Good! (1,284 reviews)
"clean and cozy, and convenient location."

Reviewed on 6 June 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
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.

Frequently asked questions

How much does a Boston vacation package cost?
You can grab a vacation package to this top destination 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?
If you’re hoping to snag a cheap Boston vacation package, consider traveling in January, February and March. You’ll usually find better rates on flights and accommodations during these quieter months — ideal for travelers wishing to save money.
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.
How to plan a trip to Boston?

  1. Pick your dates: What you plan to do in Boston and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in costs like flights, food and transportation when calculating how much to put aside for your trip to Boston. Then, pick a hotel that suits your budget, whether that’s an economical stay or a swankier retreat.
  3. Determine how many days away: Start by making a list of all the attractions you’d like to experience in Boston. Then, estimate how long you’ll need at each, along with any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that’s left is to find a Boston vacation package that brings all your bookings together.

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