Eastern Massachusetts Vacation Packages

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Your Eastern Massachusetts Vacation

Choose one of our vacation packages to Eastern Massachusetts and wander wherever your inner adventurer desires. Dining and culture are just a couple of the things you can look forward to in this exciting destination. Your trip to Eastern Massachusetts wouldn't be complete without experiencing some of its most well-known cities, starting with Boston. Two of the top attractions here include Fenway Park and TD Garden. Hyannis is another favourite city with Eastern Massachusetts travellers. Visitors to this exciting destination enjoy Cape Codder Water Park and Cape Cod Inflatable Park. From the instant you book your Eastern Massachusetts vacation to when you get back home, Expedia will be with you each step of the way.

Top Eastern Massachusetts Vacation Deals

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

Boston Lodge and Suites

4 out of 5
Dorchester
per person
Nov 1 - Nov 3
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
The Boston Harbor Hotel continues to be my absolute favorite place to stay in Boston, and my recent visit reminded me exactly why. From the moment I walked through the doors, I was greeted by the same welcoming and professional staff that makes this property truly special. The team went above and beyond by upgrading me to a suite, which was an unexpected and much-appreciated gesture that really enhanced my stay. The suite itself was beautifully appointed and comfortable, providing the perfect retreat after busy days exploring the city. What really sets this hotel apart is its unbeatable location. You simply cannot find a better spot in Boston - it's perfectly positioned for both business and leisure activities, with easy access to everything the city has to offer while maintaining that sense of waterfront tranquility. Every stay here has been delightful, and the consistency in service quality is remarkable. The Boston Harbor Hotel has earned my loyalty through their attention to detail and genuine hospitality. I'm already looking forward to my next visit!

Reviewed on Aug. 11, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on Aug. 11, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Oct 9 - Oct 13
found 18 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on Aug. 5, 2025

Where to stay in Eastern Massachusetts

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

Ready to book your vacation to Eastern Massachusetts?

 

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Eastern Massachusetts Hotel Deals

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 $257 per night from Sep 1 to Sep 2
CA $257
CA $306 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,214 reviews)
"Spacious, quiet, and sleek hotel. Also located in a super walkable area with lots to do!"

Reviewed on Aug. 13, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $280 per night from Aug 24 to Aug 25
CA $280
CA $382 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,828 reviews)
"Lovely upscale hotel. Staff are friendly, knowledgeable and helpful. This hotel is in an Ideal location, within walking distance walking distance of tourist attractions. Roof top pool is clean and enjoyable. The beds are comfortable, the bathroom and shower are clean and relaxing. I recommend staying ..."

Reviewed on Aug. 11, 2025

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 $221 per night from Sep 1 to Sep 2
CA $221
CA $313 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (3,203 reviews)
"The room and restroom were very small a bit outdated. The location was great, central to Boston areas, lobby and bar area was also very nice."

Reviewed on Aug. 11, 2025

Hilton Boston Park Plaza
See all 15,771 properties in Eastern Massachusetts
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

Discover the most popular places to visit in Eastern Massachusetts

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

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

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

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

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Eastern Massachusetts

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

CA $69
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $69
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

CA $23
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
See all activities in Eastern Massachusetts

Frequently asked questions

How much does an Eastern Massachusetts vacation package cost?
From as low as CA $759. Yes, you read that correctly. Our Eastern Massachusetts vacation packages are an awesome way to make your dollars go much further. Combine your flights, hotels and rental car and get out and see this popular destination.
How do I get a cheap travel package to Eastern Massachusetts?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got everything you need. Select the combination that best suits you and see your savings grow. We know a package deal is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 hotels across the world, which lets you customize your Eastern Massachusetts adventure.
Where should I stay in Eastern Massachusetts?
Boston is a great place to visit. This city is where you'll find impressive sights such as Fenway Park and Boston Common. Cambridge also draws in many jetsetters eager to check out some of the best attractions in Eastern Massachusetts. They include Harvard Square and Harvard University.
What are the top hotels in Eastern Massachusetts?
When it comes to properties in Boston, Hampton Inn Boston - Logan Airport and Boston Park Plaza are two excellent options. If you're also heading to Provincetown, Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel will make you feel right at home.
How far in advance should I book my Eastern Massachusetts vacation?
Savvy travelers often book as early as possible. You can generally browse through international fares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, don't despair. Discounted prices sometimes appear just weeks prior to departure.
What does an Expedia Eastern Massachusetts travel package include?
Flights, hotels and rental cars — we've got them all. With Expedia, you can create your Eastern Massachusetts package just how you like it. All you have to do is decide just what you need. Once you've made your booking, you can add extras like experiences and activities. The more you bundle, the more you save!
What should I know before booking an Eastern Massachusetts travel package?
A travel package can be easier on the credit card than individually booking everything you need for your getaway. For example, bundle your hotels, flights and rental cars and save a tidy sum. No matter your vacation goals, you're sure to find a package that best suits your budget.
Can I choose my airline with an Eastern Massachusetts Expedia vacation package?
With a vacation package, you're the boss. Whether you want to fly to Eastern Massachusetts in economy or business class, simply select from the available airline options. Expedia has access to more than 550 airline partners across the world.
If I'm not able to travel, can I cancel my Eastern Massachusetts vacation package?
Your situation can change unexpectedly, so yes. You may be able to cancel or amend your Eastern Massachusetts vacation package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your airline, hotel or car rental company may charge additional fees. Need more information? Check out our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.