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.
Surfside Hotel and Suites

Surfside Hotel and Suites

CA $913
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
8.6/10 Excellent! (1,007 reviews)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
CA $4,803
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9.4/10 Exceptional! (475 reviews)
It was our first visit to Boston. So glad we stayed at the Four Seasons on Boylston. It’s centrally located to all the attractions that were on our list. The city view trolley is located across the street from the hotel. Easy hop on and off. Staff were amazing - friendly and professional. We will definitely stay here again when we come back to Boston.

Reviewed on Aug 6, 2026

Crowne Pointe Historic Inn & Spa - Adults Only

Crowne Pointe Historic Inn & Spa - Adults Only

CA $1,233
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
9.2/10 Wonderful! (906 reviews)
Great experience from beginning to end. Great Breakfast

Reviewed on Aug 7, 2026

Harbor Hotel Provincetown

Harbor Hotel Provincetown

CA $970
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
8.2/10 Very good! (1,011 reviews)
La gentillesse du personnel

Reviewed on Aug 8, 2026

Good Hotels Boston

Good Hotels Boston

South End
CA $1,325
per person
Sep 9 - Sep 13
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8/10 Very good! (55 reviews)
Very nice people and had excellent help!

Reviewed on Aug 7, 2026

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
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.

Find hotels in Downtown Boston
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.

Find hotels in Back Bay
A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.

Seaport District

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.

Find hotels in Seaport District
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.

Find hotels in Beacon Hill
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

1 out of top 10 points of interest in this area

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.

Find hotels in North End

Ready to book your vacation to Eastern Massachusetts?

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Eastern Massachusetts 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! (4,694 reviews)
"Definitely worth the money & will stay there again anytime im in Boston"

Reviewed on Aug 7, 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $333
CA $445 total
Aug 20 - Aug 21
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 27 - Aug 28
includes taxes & fees
The Revolution Hotel
See all 16,450 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.
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Stay near popular Eastern Massachusetts attractions

A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

Fenway Park

9.2/10 (11,009 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
See properties
A soccer stadium with a crowd of spectators, a goalpost, and players in action.
Photo by The Curious Zephyr

Gillette Stadium

9.0/10 (1,182 reviews)
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's great live music and acclaimed theater scene.
See properties
A classical building with columns and a blue door, surrounded by trees and people walking.

Harvard University

9.2/10 (6,542 reviews)
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
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A park with manicured hedges, flowering plants, and a city skyline in the background.

Boston Common

9.4/10 (18,299 reviews)
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.
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A modern building with 'GARDEN' signage, a waterfront, and a cable-stayed bridge.

TD Garden

9.2/10 (7,449 reviews)
Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.
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A historic church with a pointed roof and a large tower, surrounded by modern buildings and a well-maintained park with flowers and trees.

Copley Square

9.4/10 (7,327 reviews)
Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax.
See properties
A waterfront scene with a boat docked at a pier, a city skyline in the background, and a red and white ferry on the right.

Boston Harbor

9.6/10 (5,623 reviews)
Adore Boston’s charming working harbor from the waterfront or head out by boat to get to know it more intimately.
See properties

Frequently asked questions

How much does an Eastern Massachusetts vacation package cost?
From as low as CA $913. 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.