Boston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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

Top Boston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kasa South Side Pittsburgh

Kasa South Side Pittsburgh

4 out of 5
South Side Flats
per person
Jul. 19 - Jul. 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.8/10 Excellent! (56 reviews)
Directions regarding parking were at times confusing...counter tops were sticky...had to clean before using...otherwise everything was as expected

Reviewed on Jun. 2, 2024

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
per person
Jul. 19 - Jul. 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.4/10 Very Good! (1,003 reviews)
Easy check inn never went to the front desk to check in or out

Reviewed on Jun. 3, 2024

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
Jul. 19 - Jul. 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Modern clean hotel .

Reviewed on May 13, 2024

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Jul. 19 - Jul. 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
7.6/10 Good! (2,724 reviews)
The hotel was very easy to get to from out of town, conveniently located a very short walk across the bridge to both Acrisure and PNC, stadiums and bars and restaurants downtown. Beautiful park and scenery. Nothing was too far to walk to or subway was super convenient and free. Staff were friendly and knowledgeable. Saur at the concierge‘s desk was absolutely wonderful. You can tell that he really likes helping people. Very kind man. The only thing and it’s totally personal is the brown colour in the hallways and curtains could be updated to a more fun colour. The gray on the 4th floor was a little better of a choice. Thank you for a great weekend

Reviewed on Jun. 3, 2024

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
per person
Jul. 19 - Jul. 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.2/10 Very Good! (659 reviews)
Staff at front desk were very friendly and helpful. Hotel was clean. Although room was small it had everything we needed. Would stay again!

Reviewed on Jun. 3, 2024

Boston Hotel Deals

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 $238 per night from Jun. 30 to Jul. 1
CA $238
CA $272 total
includes taxes & fees
Jun 30 - Jul 1
9/10 Wonderful! (1,335 reviews)
"Nice hotel"

Reviewed on Jun. 3, 2024

Omni William Penn Hotel
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 $226 per night from Jun. 13 to Jun. 14
CA $226
CA $258 total
includes taxes & fees
Jun 13 - Jun 14
7.6/10 Good! (2,742 reviews)
"The hotel was very easy to get to from out of town, conveniently located a very short walk across the bridge to both Acrisure and PNC, stadiums and bars and restaurants downtown. Beautiful park and scenery. Nothing was too far to walk to or subway was super convenient and free. Staff were friendly ..."

Reviewed on Jun. 3, 2024

Wyndham Grand Pittsburgh Downtown
Homewood Suites by Hilton Pittsburgh Downtown
Homewood Suites by Hilton Pittsburgh Downtown
3 out of 5
1410 Smallman Street, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Jul. 2 to Jul. 3
CA $231
CA $264 total
includes taxes & fees
Jul 2 - Jul 3
8.8/10 Excellent! (1,004 reviews)
"Easily walkable to Strip and nearby attractions. Awesome location!"

Reviewed on Jun. 4, 2024

Homewood Suites by Hilton Pittsburgh Downtown
See all 1,487 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

Frequently asked questions

How much does a Boston vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Boston from just CA $1,069. And the more you bundle, the more money you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Boston?
Crafting your own Boston vacation package with Expedia is one of the easiest ways to save. We offer access to over 550 airlines and 1,000,000 hotels worldwide. With such a broad range to pick from, you’ll have no trouble pulling together your perfect getaway.
Where should I stay in Boston?
There’s plenty to do in Boston, so stay close to its best sights and spend more time sightseeing. McKeesport Little Theater is one place to put on your itinerary.
How far in advance should I book my Boston vacation?
Savvy travelers often reserve their seats as early as possible. You can usually browse through international airfares on Expedia up to 12 months before your flight. If you’re purchasing your ticket at the last minute, don’t stress. Low prices occasionally appear just weeks prior to departure.
What does an Expedia Boston travel package include?
It comes down to what you’re looking for. If you’re traveling by yourself, you might decide to bundle hotels and flights. Bringing the whole crew to Boston? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility to customize your travel package.
What should I know before booking a Boston travel package?
Bundling your bookings into a Boston vacation package is the easiest way to organize your trip. Not only that, you’ll save when you combine your flights, hotels and car rentals. Once you’ve booked, why not add on an activity or a tour?
Can I choose my airline with a Boston Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines all over the world. Our vacation packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Boston vacation package?
Because we understand life is full of surprises, the answer is yes. For further information, check out our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change it for free. Your hotel, airline or car rental company may impose a fee if your booking is older than that.

Discover the most popular places to visit in Boston

Image for Northeast Paddleboard Company

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

Other vacations you might like

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