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 $1,096 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.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was CA $1,023, price is now CA $769 per person
CA $769
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (254 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.

Reviewed on Jan 31, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,301, price is now CA $1,497 per person
CA $1,497
per person
May 16 - May 18
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!

Reviewed on Mar 14, 2026

enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Price was CA $1,466, price is now CA $1,063 per person
CA $1,063
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
My go to whenever in Boston

Reviewed on Mar 13, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $1,328, price is now CA $989 per person
CA $989
per person
May 16 - May 18
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Beachside Village Resort

Beachside Village Resort

3 out of 5
Price was CA $1,284, price is now CA $969 per person
CA $969
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (101 reviews)
Very clean and quiet place to relax. Very friendly and professional! We will come back!

Reviewed on Nov 10, 2025

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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(193 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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
The price is CA $211 per night from Apr 5 to Apr 6
CA $211
CA $302 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (4,524 reviews)
Great room and amenities

Reviewed on Mar 17, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Mar 22 to Mar 23
CA $195
CA $283 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (3,128 reviews)
AI automated the services. It was difficult to obtain a crib, a rollaway bed, etc., and there was no room service. I would not stay here again unless necessary.

Reviewed on Mar 18, 2026

Hilton Boston Park Plaza
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 $157 per night from Apr 5 to Apr 6
CA $157
CA $230 total
Apr 5 - Apr 6
includes taxes & fees
9.6/10 Exceptional! (4,066 reviews)
It was okay. We liked the location of the hotel.

Reviewed on Mar 17, 2026

Seaport Hotel Boston
See all 4,134 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
Family Vacations
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 CA $769. 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 featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

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

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

4.5/5(27 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 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 $72
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 $108
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $32
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.