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.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was CA $1,077, price is now CA $764 per person
CA $764
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
The hotel grounds are extremely well maintained; the views of the water and benches to relax on are fantastic! We had a great stay with our two teenagers. It was out of the hustle and bustle of the city. A wonderful place!

Reviewed on Oct 26, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $1,539, price is now CA $982 per person
CA $982
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Excellent as always.

Reviewed on Oct 27, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $4,902, price is now CA $3,408 per person
CA $3,408
per person
Nov 26 - Dec 2
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (465 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $1,334, price is now CA $935 per person
CA $935
per person
Jan 8 - Jan 10
found 7 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
设施很新，SPA桑拿体验特别好，晚餐气氛很棒

Reviewed on Oct 20, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was CA $2,540, price is now CA $1,817 per person
CA $1,817
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)

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

Ready to book your vacation to Eastern Massachusetts?

 

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Eastern Massachusetts Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Nov 26 to Nov 27
CA $258
CA $357 total
Nov 26 - Nov 27
includes taxes & fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Nov 26 to Nov 27
CA $145
CA $169 total
Nov 26 - Nov 27
includes taxes & fees
The Revolution Hotel
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 $190 per night from Nov 26 to Nov 27
CA $190
CA $269 total
Nov 26 - Nov 27
includes taxes & fees
9.6/10 Exceptional! (5,160 reviews)
"."

Reviewed on Oct 26, 2026

Seaport Hotel Boston
See all 15,936 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

What to do in Eastern Massachusetts

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

CA $24
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

CA $71
per adult
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $71
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Eastern Massachusetts

Frequently asked questions

How much does an Eastern Massachusetts vacation package cost?
From as low as CA $764. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.