The Port Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in The Port

Price found within the past 48 hours. Click for updated prices.
Sesuit Harbor House

Sesuit Harbor House

CA $946
per person
Sep 10 - Sep 13
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (196 reviews)
Wonderful stay and would stay again

Reviewed on Aug 10, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
CA $2,525
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (475 reviews)
Overrated

Reviewed on Aug 10, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
CA $1,967
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,298 reviews)
The Mansion at Ocean Edge

The Mansion at Ocean Edge

CA $2,261
per person
Sep 10 - Sep 13
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (1,000 reviews)
We had a really nice time. We are a family of 5 with tweens. We stayed at the mansion. Pros: - the beach and the beach staff were lovely. the beach is just so cool. very clean. kids had fun with other kids, going out on the flats, playing with the hermit crabs, and wading in the water. as a parent i appreciated not fearing they were going to drown or get pulled by the waves (it was very calm). - the front lawn. kids enjoyed this during the evenings. it was a nice wat to unwind and let the kids run and play games. - the golf. my kids and husband enjoyed playing 18 and 9 holes. We also went over one evening and just used the range for an hour or so. very friendly staff and a very nice course. The cons - It did not have a high end feel to it. we were checked in and that was it. not a big deal, but it was touted as high end. I wouldn't have had that expectation otherwise. - the room air conditioning - the room itself was spacious and felt clean. the air conditioning was like a monster. it was one that came on and then turned off until the room got hot and then kicked back on. it literally woke us up every night multiple times because it was so loud - like an autobody shop or monster screeching. - inflated prices. I expect this because we're at a nice resort and a lot goes into that. but the prices were very elevated. $26 pizza on the lawn and a glass of wine and water was $30. if you're used to city/resort pricing this won't surprise you. Overall - It was a solid 'B' stay

Reviewed on Aug 11, 2026

The Charles Hotel

The Charles Hotel

West Cambridge
CA $1,637
per person
Sep 24 - Sep 27
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,006 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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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.

A historic building with ornate architecture, a staircase, and a tree in front.

Back Bay

1 out of top 10 points of interest in this area

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.

Seaport District

1 out of top 10 points of interest in this area

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

A street lamp with a lit bulb, surrounded by trees and a brick building.

Beacon Hill

1 out of top 10 points of interest in this area

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

A bustling riverside area with a prominent building featuring a large arched entrance, a dock with a boat, and a crowd of people.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

The Port Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $264
CA $354 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (4,737 reviews)
"We had a very nice stay. We picked this hotel because they had a pool. This was a special trip for my 5 year old son and I. The front desk told us that the pool was open until 10 pm. I'm very glad I checked in the room because it was only open until 8. Had we gone to dinner first we would have missed ..."

Reviewed on Aug 11, 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
CA $328
CA $439 total
Aug 30 - Aug 31
includes taxes & fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $190
CA $221 total
Aug 13 - Aug 14
includes taxes & fees
The Revolution Hotel
See all 4,151 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.

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 $946. 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 $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 $118
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 $48
per adult
86% 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.