Boston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Boston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Only parking options are valet for $32 extra or park in the street on some very sketchy streets

Reviewed on Jul. 23, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8/10 Very Good! (2,882 reviews)
One of the front desk staff members was very rude and dismissive when I called about somebody screaming in the hallway at 6 a.m. The rest of the staff was nice. The hotel guests were pretty noisy most of the time.

Reviewed on Jul. 25, 2025

Placemakr Downtown Pittsburgh

Placemakr Downtown Pittsburgh

4 out of 5
Downtown Pittsburgh
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
7.2/10 Good! (10 reviews)
Practical and accessible

Reviewed on Jul. 12, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
Location, location, location. The property layout is super convenient with easy access to the convention center and local amenities. Like many properties, I felt the room was not as updated and fresh as the public areas were. Check-in was extremely fast and efficient. The value is in the proximity to the freeway and downtown life.

Reviewed on Jun. 22, 2025

TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
Lawrenceville
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.6/10 Excellent! (819 reviews)
We had a micro room and it was perfect for our three days in Lawrenceville! The history of the building was fascinating and the manager who let us in our room when we forgot our room key was so nice and very knowledgeable about the building and the area. We loved the accommodations especially the Beekman 1802 bath products!😃

Reviewed on Jul. 25, 2025

Ready to book your vacation to Boston?

 

Choose your dates

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 CA $163 per night from Jul 27 to Jul 28
CA $163
CA $186 total
Jul 27 - Jul 28
includes taxes & fees
8/10 Very Good! (2,960 reviews)
"Nice overall property! Parking was a bit chaotic and checkin took longer than it should have. Overall it did what we needed."

Reviewed on Jul. 25, 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 CA $196 per night from Aug 17 to Aug 18
CA $196
CA $224 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,571 reviews)
"Very nice hotel and staff"

Reviewed on Jul. 25, 2025

Omni William Penn Hotel
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr, Pittsburgh, PA
The price is CA $176 per night from Aug 24 to Aug 25
CA $176
CA $201 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (872 reviews)
"We had a wonderful 2 night stay at the Landing hotel. Beautiful property and surrounding area. Staff were amazing. Fastest Valet I've ever experienced. Couple minor issues, the power drapes didn't always work, the mini fridge popped the breaker once but again all minor. We will be back."

Reviewed on Jul. 24, 2025

The Landing Hotel at Rivers Casino
See all 1,715 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Boston

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.

Northeast Paddleboard Company

Frequently asked questions

How much does a Boston vacation package cost?
You'll find cheap prices from CA $774 on Expedia for your Boston break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Boston costs.
What are the cheapest months to go to Boston?
You're likely to find lower prices and greater availability in January, February and March. Browse our cheap Boston vacation packages and you could land some great off-season deals.
How many days is enough for Boston?
Dedicate around 2 days for your Boston vacation if you want to enjoy all that makes this place special. Stroll around key areas, including Versailles and Dravosburg. Then check out major sights such as Grand Theatre and Round Hill Park. With a well-organized itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Boston? Consider squeezing in an excursion or two.
How to find the best Boston package deals?
Finding a cheap Boston package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Boston package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Boston vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a customized Boston vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Boston?
If you're planning a spur-of-the-moment Boston vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Boston?

  1. Choose when to go: Check your diary and get packing. Your preferred time of year and the available activities will also help you decide when to visit Boston.
  2. Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will likely be the largest expense during your trip to Boston.
  3. Decide how long to go away for: Now that you're more familiar with Boston, you can figure out the ideal length of your vacation. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Boston vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.