The Port Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top Holiday Package Deals in The Port

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,504, price is now CA $667 per person
CA $667
per person
Dec 20 - Dec 23
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,202, price is now CA $1,658 per person
CA $1,658
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
!

Reviewed on Nov 10, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,556, price is now CA $1,032 per person
CA $1,032
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Price was CA $2,032, price is now CA $1,360 per person
CA $1,360
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (502 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,232, price is now CA $2,174 per person
CA $2,174
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

Where to stay in The Port

Find the best The Port areas and neighborhoods for the activities you enjoy most. Learn more about The Port
Quincy Market with an American flag, historic buildings, and a clock tower in the background.

Downtown Boston

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Find hotels in Downtown Boston

The Port Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Nov 22 to Nov 23
CA $187
CA $275 total
Nov 22 - Nov 23
includes taxes & fees
9.2/10 Wonderful! (5,020 reviews)
"Wonderful room and amenities including restaurants."

Reviewed on Nov 12, 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Nov 26 to Nov 27
CA $130
CA $152 total
Nov 26 - Nov 27
includes taxes & fees
9/10 Wonderful! (3,034 reviews)
"We thought the outside bathroom was going to be a problem, but it was not! They really make sure the bathroom is clean all the time and that we have everything we need. The decoration is great at the hotel. We will come back really soon:)"

Reviewed on Nov 12, 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Nov 23 to Nov 24
CA $134
CA $204 total
Nov 23 - Nov 24
includes taxes & fees
9.6/10 Exceptional! (5,215 reviews)
"I unfortunately had a not so good experience from the moment we walked in. The check in process took approximately twenty minutes (even though I pre-checked in), we weren’t greeted or acknowledged, the desk staff didn’t even try to help us or greet us and it was extremely uncomfortable and frustrating. ..."

Reviewed on Nov 12, 2026

Seaport Hotel Boston
See all 3,994 properties in The Port
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.
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Frequently asked questions

How much does a The Port vacation package cost?
Be ready to book, because a getaway to The Port starts from an enticing CA $667. When you bundle your flights, hotels and more into a package, you'll enjoy the biggest deals.
How do I get a cheap travel package to The Port?
Our The Port vacation packages mean plenty of savings for the savvy explorer. For the best deal, simply combine your hotel, flights and extras (such as activities) into an affordable package. But great bargains are only the start of your next memorable adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 hotel options worldwide to pick from. Whatever your budget or style, there's a vacation package here just for you.
Where should I stay in The Port?
Visitors come from near and far to see Harvard Square and Massachusetts Institute of Technology in The Port. Stay near these must-see attractions and visit them whenever you please.
What are the top hotels in The Port?
Get your vacation off to a good start by locking in a room at The Windsor Inn. It's one of most popular properties in The Port. Another comfortable option is Cambridge Urban Oasis Apartment Betw M. I. T. And Harvard.
How far in advance should I book my The Port vacation?
Your safest bet is to book early. Air carriers usually advertise flights up to a year ahead of departure, and this is an ideal opportunity to score some rock-bottom prices. Boss just told you to take some vacation time next week? No sweat. Expedia are never short of fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia The Port travel package include?
From airfares and hotels to rental cars, Expedia can help you shape a The Port package that works for you. Heading off for a few weeks? Look into a hotel, rental car and flight bundle. If you're taking a quick break, a hotel and flight deal could suit you better. Tours and activities can be added once you've made your booking. Our packages make it a breeze to save and plan.
What should I know before booking a The Port travel package?
So many places to explore, so many things to see and do. With a package, you'll be able to check more of them off your list. Bundle your flights, hotels and rental cars and score big savings.
Can I choose my airline with a The Port Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Simply select the carrier you want and craft your ideal The Port vacation.
If I'm not able to travel, can I cancel my The Port vacation package?
You sure can, and we're here to help. You may be able to amend or cancel your The Port vacation package at no cost within 24 hours of booking. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If your circumstances suddenly change, have a look at our Customer Service Portal for further information.

Stay near popular The Port attractions

Middlesex Lounge

After visiting Middlesex Lounge, make a plan to see the other sights and activities in Cambridge. While in this walkable area, you can savor the top-notch restaurants.
See properties

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $69
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $65
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.