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.
Studio Allston Hotel

Studio Allston Hotel

4 out of 5
Brighton
Price was CA $2,128, price is now CA $1,481 per person
CA $1,481
per person
May 13 - May 20
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (1,247 reviews)
It's a nice hotel. Quirky, but it's quiet and conveniently located.

Reviewed on Mar 8, 2026

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Price was CA $2,767, price is now CA $1,771 per person
CA $1,771
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (435 reviews)
All accommodations was absolutely amazing! The experiece started with thw doorman upon arrival ,the concierge service, room awrvice, reataurants, gym, everything was perfect! The location was great. Will stay again on our next visit.

Reviewed on Mar 2, 2026

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Price was CA $2,735, price is now CA $1,843 per person
CA $1,843
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (2,266 reviews)
The valet parking is an additional $60.00

Reviewed on Mar 11, 2026

Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham

3.5 out of 5
Price was CA $2,500, price is now CA $1,721 per person
CA $1,721
per person
May 13 - May 20
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8/10 Very Good! (2,788 reviews)
Very nice breakfast.

Reviewed on Mar 9, 2026

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Price was CA $2,771, price is now CA $1,968 per person
CA $1,968
per person
May 13 - May 20
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
7.4/10 Good! (851 reviews)
Clean room, adequate breakfast, friendly staff. Free parking. Only issue was it took a long time for the shower water to get hot. Good budget option in an are where few exist.

Reviewed on Mar 4, 2026

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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

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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 $207 per night from Mar 22 to Mar 23
CA $207
CA $297 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (4,505 reviews)
Nice

Reviewed on Mar 11, 2026

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 $184 per night from Mar 23 to Mar 24
CA $184
CA $270 total
Mar 23 - Mar 24
includes taxes & fees
8.4/10 Very Good! (3,114 reviews)
Choose the wicked small room and it was perfectly fine for my wife and I.

Reviewed on Mar 12, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $207 per night from Mar 19 to Mar 20
CA $207
CA $241 total
Mar 19 - Mar 20
includes taxes & fees
9.2/10 Wonderful! (6,345 reviews)
Terrific location for seeing the Boston sites!

Reviewed on Mar 12, 2026

Harborside Inn Of Boston
See all 16,145 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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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

4.5/5(305 reviews)

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

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

4.5/5(27 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium
Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 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.

Boston Common

What to do in Eastern Massachusetts

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
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

CA $23
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

CA $69
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
See all activities in Eastern Massachusetts

Frequently asked questions

Can I cancel my flight booking to Eastern Massachusetts due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for most travel queries, including about flight changes due to COVID-19. For greater peace of mind, look over the terms and conditions of your preferred carrier before booking.
What's the best way to find cheap flights to Eastern Massachusetts that have flexible change policies?
When it comes to traveling these days, flexibility is key. That's why we've added a "No change fee" filter to help you find flexible, low-priced flights to Eastern Massachusetts. It's to the left of your screen just underneath the "Flexible change policies" subheading.
What are some of the general tips for travelers to Eastern Massachusetts during the COVID-19 outbreak?
With new safety guidelines in place, travel looks a bit different these days. Here's what you should know before you get on that plane to Eastern Massachusetts:
  • Find out if any travel restrictions apply to your origin and destination before booking your flight. Also check if there are any special conditions you'll need to follow on arrival, such as mandatory quarantining.
  • Keep your face mask on during airport screening. A TSA employee will require you to temporarily lower your mask for ID purposes.
  • Rather than handing a TSA employee your boarding pass, position it straight on the scanner yourself. When that's done, hold it up for inspection.
  • You can take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. This will need to be taken out for X-ray screening.
  • Remove items from your pockets, such as your wallet and phone, and place them in your carry-on instead of the bins. This will reduce handling during the screening process.
  • If you're taking food on board, put it in a clear plastic bag and then into a scanning bin. This lessens the likelihood that a TSA employee will need to handle your carry-on bag or food container for closer inspection.

Which airlines fly to Eastern Massachusetts?
Cape Air offers flights into or near Eastern Massachusetts, including 1785 that touch down at Logan Intl. Airport (BOS) each month. Choose your vacation dates and then secure your airfare early to get the best deal.
How can I find cheap tickets to Eastern Massachusetts?
One of the easiest ways to snare cheap tickets to Eastern Massachusetts is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It'll reveal the cheapest prices for nearby days. The best price for a flight to Eastern Massachusetts in the last seven days was . Booking well ahead of time will usually help you pick up an even better deal.
How much is a flight to Eastern Massachusetts?
One-way flights departing from () sold for just in the last seven days. During this time, the price of a return air ticket to Eastern Massachusetts varied between and . If you spot a good deal, grab it quickly — these prices don't stick around for long.
What are the most popular airports to fly into in Eastern Massachusetts?
Start organizing your Eastern Massachusetts trip by securing a seat on one of the 12051 monthly flights to Logan Intl. Airport (BOS). This is the region's main point of entry.
When is the cheapest time to fly to Eastern Massachusetts?
If you'd rather spend your cash on having fun in Eastern Massachusetts rather than on flying there, take off early in the week. The cheapest day to travel is usually Tuesday, followed by Monday. With many people traveling on weekends, Saturday often has the most expensive fares.
How much is a plane ticket to Eastern Massachusetts?
Flights to Eastern Massachusetts ranged from to in the last seven days. Generally, the earlier you make a reservation, the bigger the bargain.
Which airlines with flights to Eastern Massachusetts employ COVID-19 cleanliness policies?
As travel restrictions start to lift, many airlines are now servicing flights with new strategies including physical distancing and enhanced disinfection measures. Here's what multiple carriers are doing to help stop the spread of COVID-19:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.