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
Price found within the past 48 hours. Click for updated prices.
  • Game room
    Jul 28 - Jul 30

    Meco Hotel - Hostel + Flight

    West End
    2 nights
    2.0 star property
    8.6/10 - Excellent (449 reviews)
    "LOVED IT VERY MUCH"
    Reviewed June 8, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $1,517
    CA $849
    per traveller
    found 1 day ago
    Meco Hotel - Hostel
  • Property entrance
    Aug 26 - Aug 30

    Sea Crest Beach Resort + Flight

    North Falmouth
    4 nights
    3.5 star property
    7.8/10 - Good (304 reviews)
    "/"
    Reviewed June 10, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,863
    CA $1,022
    per traveller
    found 1 day ago
    Sea Crest Beach Resort
  • Suite, Multiple Beds (John Adams Presidential Suite)
    Aug 28 - Aug 30

    Boston Harbor Hotel + Flight

    North End
    2 nights
    5.0 star property
    9.8/10 - Exceptional (1,003 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,805
    CA $1,105
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • Breakfast meal
    Aug 26 - Aug 30

    By the Sea Guests Bed & Breakfast & Suites + Flight

    Dennis Port
    4 nights
    3.5 star property
    9.2/10 - Wonderful (188 reviews)
    "Yes"
    Reviewed June 4, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,743
    CA $1,086
    per traveller
    found 1 day ago
    By the Sea Guests Bed & Breakfast & Suites
  • Oceanfront Efficiency, 1 King Bed
    Aug 26 - Aug 30

    Chatham Tides + Flight

    South Chatham
    4 nights
    2.5 star property
    9.4/10 - Exceptional (708 reviews)
    "The room was spotless and nicely designed. We had a room right on the water and it was wonderful to wake up to the view every morning. The only amenity I would suggest would be a station to rinse off sandy feet."
    Reviewed June 7, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,054
    CA $1,380
    per traveller
    found 1 day ago
    Chatham Tides

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
Downtown Boston

Downtown Boston

4.5/5(197 area reviews)

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

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 $200 per night from Jul 5 to Jul 6
CA $200
CA $233 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (2,667 reviews)
"I loved this hotel"

Reviewed on Jun 9, 2026

The Revolution Hotel
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 $289 per night from Jun 14 to Jun 15
CA $289
CA $394 total
Jun 14 - Jun 15
includes taxes & fees
Omni Boston Hotel at the Seaport
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 $264 per night from Jul 5 to Jul 6
CA $264
CA $355 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (4,442 reviews)
"Great coffee maker. They left a coffee k cup inside it."

Reviewed on Jun 10, 2026

Seaport Hotel Boston
See all 4,124 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

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 . 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.

Discover the most popular places to visit in The Port

Fenway Park

Fenway Park

4.5/5(310 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Boston Harbor

Boston Harbor

4.5/5(93 reviews)

Adore Boston’s charming working harbor from the waterfront or head out by boat to get to know it more intimately.

Boston Harbor
Harvard University

Harvard University

4.5/5(284 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $73
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 $116
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
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.