Boston Vacation Packages

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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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
per person
Nov. 8 - Nov. 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8/10 Very Good! (843 reviews)
Average hotel, uninterested staff

Reviewed on Sep. 15, 2024

Kimpton Hotel Monaco Pittsburgh, an IHG Hotel

Kimpton Hotel Monaco Pittsburgh, an IHG Hotel

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Nov. 8 - Nov. 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,040 reviews)
The room was spotless and the staff was incredible.

Reviewed on Sep. 11, 2024

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
Nov. 8 - Nov. 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,004 reviews)
Centrally located to restaurants and clubs. Fifteen minute walk to PNC and twenty minute ride from airport. Only one thing the Hotel needs is a good quality complementary coffe for its guest and maybe some lemon water for the lobby....not a biggie thou. Definitely Definitely staying here again!!

Reviewed on Sep. 9, 2024

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
per person
Nov. 8 - Nov. 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.4/10 Very Good! (1,008 reviews)
We were delighted at check in to get upgraded for no additional cost the most wonderful room. Thanks!

Reviewed on Sep. 20, 2024

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
Nov. 8 - Nov. 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
7.6/10 Good! (70 reviews)
Communication was a bit lacking, they picked up after I called 4 times when the code to the front door wasn’t working. I also emailed but got a response pretty late, and by that time someone already let me in the door. Code to the room also took a few tries to work. I entered the same code a couple of times for it to actually open. Property itself was good! Relatively clean with a full kitchen, mainly it’s just the communication that was lacking.

Reviewed on Aug. 13, 2024

Ready to book your vacation to Boston?

 

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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
The price is CA $194 per night from Oct. 10 to Oct. 11
CA $194
CA $221 total
includes taxes & fees
Oct 10 - Oct 11
7.6/10 Good! (2,862 reviews)
"Overall this was a great hotel. It was conveniently located close to everything we wanted to see and do. It was clean and the staff where good. The room itself was clean however there was no safe in the room and the sliding door on the bathroom was broken and required effort to operate. We had to ..."

Reviewed on Sep. 19, 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
The price is CA $216 per night from Oct. 8 to Oct. 9
CA $216
CA $246 total
includes taxes & fees
Oct 8 - Oct 9
9/10 Wonderful! (1,021 reviews)
"Close walk to lots of things in downtown area"

Reviewed on Sep. 19, 2024

Homewood Suites by Hilton Pittsburgh Downtown
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 CA $202 per night from Sep. 29 to Sep. 30
CA $202
CA $230 total
includes taxes & fees
Sep 29 - Sep 30
8/10 Very Good! (865 reviews)
"Cute hotel, right downtown. Easy valet parking, walkable to red line train. Room was small but perfect for 2."

Reviewed on Sep. 15, 2024

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,522 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

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 $1,036. 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.