Waterfront Vacation Packages

Top Holiday Package Deals in Waterfront

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

The Whitney Hotel

Beacon Hill

CA $1,188

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (587 reviews)

Boston Harbor Hotel

North End

CA $1,642

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.8/10 Exceptional! (1,015 reviews)

Four Seasons Hotel Boston

Bay Village

CA $2,171

per person

Sep 21 - Sep 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (474 reviews)

perfecto

Reviewed on Jun 8, 2026

The Cove at Yarmouth by Westgate Resorts

CA $1,338

per person

Oct 1 - Oct 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.2/10 Wonderful! (268 reviews)

P Indoor pool and hot tub loved and the outdoor Shack was great

Reviewed on Jun 8, 2026

Good Hotels Boston

South End

CA $1,459

per person

Sep 9 - Sep 13

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

8/10 Very good! (55 reviews)

This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Where to stay in Waterfront

Find the best Waterfront areas and neighborhoods for the activities you enjoy most. Learn more about Waterfront

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.

Waterfront Hotel Deals

Boston Harbor Hotel

70 Rowes Wharf Boston MA

Fully refundableReserve now, pay when you stay

CA $750

CA $874 total

Aug 20 - Aug 21

includes taxes & fees

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Fully refundableReserve now, pay when you stay

CA $348

CA $463 total

Jul 31 - Aug 1

includes taxes & fees

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

CA $202

CA $235 total

Aug 2 - Aug 3

includes taxes & fees

9/10 Wonderful! (2,775 reviews)

"Located conveniently to everything. Very safe neighborhood. The rooms are comfortable and clean as were the communal bathrooms. It’s a very good value for Boston."

Reviewed on Jul 26, 2026

See all 4,158 properties in Waterfront

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 Waterfront vacation package cost?

The cheapest Waterfront package is CA $1,188, so your dream trip can become a reality — without spending an arm and a leg. Bundle flights, hotels, car rentals and more to custom build a package that fits you.

How do I get a cheap travel package to Waterfront?

Find flights that fit your schedule, add a hotel room to your booking and see how much you save with a Waterfront vacation package. It's that easy! From flights and hotels to activities and rental cars, Expedia makes traveling cheaply a cinch. And with over 550 airlines and 1,000,000 properties around the world to select from, you'll never be short of choice.

Where should I stay in Waterfront?

Urban adventurers come from near and far to see Fenway Park and TD Garden in Waterfront. Book a room close to these popular attractions and visit them whenever you please.

What are the top hotels in Waterfront?

If it's your very first time in Waterfront, book a room at Boston Marriott Long Wharf or Boston Harbor Hotel. Both will make you feel at home and are favorites with many travelers.

How far in advance should I book my Waterfront vacation?

Savvy travelers often reserve their seats as early as possible. You can normally compare international fares on Expedia up to 12 months before your intended flight. If you're late to book, fear not. Budget prices sometimes appear just weeks before departure.

What does an Expedia Waterfront travel package include?

Select from a combination of flights, rental cars and hotels. Once you've made your booking, you can add the fun stuff like activities and tours. Want to pick your airfare class? That's also easy to do. The choice is yours when it comes to arranging your dream Waterfront escape.

What should I know before booking a Waterfront travel package?

You'll pick up impressive savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything in one place will make your trip planning easier. So why waste time or money? Whether you're organizing a luxury romantic escape or a budget family adventure, browse our package deals today.

Can I choose my airline with a Waterfront Expedia vacation package?

Expedia has access to more than 550 airline partners worldwide, so you definitely can. Just choose the airline you want and put together your ideal Waterfront vacation.

If I'm not able to travel, can I cancel my Waterfront vacation package?

Because we understand life can throw you a few curveballs, the answer is yes. To learn more, visit our Customer Service Portal. But generally speaking, if you've booked your Waterfront vacation package in the last 24 hours, you may be able to change or cancel it free of charge. Your hotel, airline or car rental company may charge a fee if your booking is older than that.