Southeast Massachusetts Vacation Packages

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Your Southeast Massachusetts Vacation

Our Southeast Massachusetts vacation packages provide an affordable, easy and immersive way to enjoy all that this exciting destination has to offer. If it's festivals and history you're looking for, this is the place to be. With so much to see on a trip to Southeast Massachusetts, it can be tricky to know where to start. Kick off your journey in Hyannis at Cape Codder Water Park and Cape Cod Inflatable Park — two much-loved attractions here. Another city worth adding to your itinerary is Braintree. Don't miss Nantasket Beach and Wollaston Beach. Expedia has flights, hotels and everything else you need to help you organize your very own tailored Southeast Massachusetts vacation today.

Top Southeast Massachusetts Vacation Deals

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

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,063, price is now CA $1,329 per person
CA $1,329
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Good room, and area. Paper thin walls. Amenity fees tacked on for your stay at the front desk. For WiFi!

Reviewed on Mar 25, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $5,481, price is now CA $3,434 per person
CA $3,434
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on Mar 23, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $5,543, price is now CA $3,624 per person
CA $3,624
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (238 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,402, price is now CA $2,226 per person
CA $2,226
per person
Apr 25 - Apr 29
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Room was spacious, clean & well set up. Nice that they use Dyptique hand soap shampoo & shower gel. That is a 5 star touch. Bed was nice and very quiet location.

Reviewed on Mar 22, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,524, price is now CA $1,652 per person
CA $1,652
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Where to stay in Southeast Massachusetts

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

Nantucket Town

5/5(2 area reviews)

Discover the charm of Nantucket, a historic New England seaport town, with its museums like the Nantucket Whaling Museum and picturesque landscapes. Enjoy local shops, restaurants, and explore key localities such as Surfside and Siasconset.

Find hotels in Nantucket Town

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Southeast Massachusetts Hotel Deals

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Mar 30 to Mar 31
CA $210
CA $320 total
Mar 30 - Mar 31
includes taxes & fees
8.6/10 Excellent! (502 reviews)
Hotel was clean and well decorated. Room had Keurig with coffee and tea pods as well as needed condiments for such. Bath items like a robe, shampoo, soap, moisturizer are provided along with plenty of fresh towels. Child enjoyed the splash pad and lazy river. A tad busy right after school, less crowded ...

Reviewed on Mar 25, 2026

Margaritaville Resort Cape Cod
Sonesta Select Boston Foxborough Mansfield

Sonesta Select Boston Foxborough Mansfield

3 out of 5
35 Foxborough Boulevard Foxborough MA
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Apr 19 to Apr 20
CA $131
CA $147 total
Apr 19 - Apr 20
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Good

Reviewed on Mar 23, 2026

Sonesta Select Boston Foxborough Mansfield
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Apr 1 to Apr 2
CA $157
CA $195 total
Apr 1 - Apr 2
includes taxes & fees
8.8/10 Excellent! (1,553 reviews)
Staff was very welcoming. The room I had was damp, and the carpet was quite musty.

Reviewed on Mar 22, 2026

Bayside Resort Hotel
See all 11,266 properties in Southeast 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 Southeast Massachusetts

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
Cape Cod National Seashore showing general coastal views and tranquil scenes

Cape Cod National Seashore

5/5(19 reviews)

Covering over miles of shoreline around Cape Cod, this national park offers endless things to see and do regardless of the season.

Cape Cod National Seashore
Hyannis Harbor featuring a sunset and a bay or harbour as well as a small group of people

Hyannis Harbor

4.5/5(33 reviews)

See the Cape Cod peninsula from a different perspective by riding a boat out of this picturesque harbor or wandering along its docks and jetties.

Hyannis Harbor

Frequently asked questions

Can I cancel my flight booking to Southeast Massachusetts due to COVID-19?
In response to these difficult times, many air carriers are offering greater flexibility. Click through to our Customer Service Portal to get important information about changing or canceling your flight due to COVID-19.
What's the best way to find cheap flights to Southeast Massachusetts that have flexible change policies?
By using our handy "No change fee" filter, that's how. Simply enter your travel details, click the "Search" button, then select the box directly underneath the "Flexible change policies" heading (to the left of your screen). Expedia makes it a snap to find flexible and affordable fares to Southeast Massachusetts.
What are some of the general tips for travelers to Southeast Massachusetts during the COVID-19 outbreak?
If it's your first time traveling during the COVID-19 pandemic, you'll notice plenty of new rules and standards in place. Take note of these tips and make your journey to Southeast Massachusetts a smooth one:
  • Before locking in your flight, find out if any travel restrictions or bans apply — in both your destination and origin. Get up-to-date information by reviewing government websites.
  • Wear a face mask even during airport screening. A TSA employee will require you to temporarily lower your mask for ID purposes.
  • You're no longer required to hand your boarding pass (paper or electronic) directly to a TSA employee. Instead, place your pass on the scanner and then hold it up for the agent to visually inspect it.
  • You're allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. You'll need to remove it for screening.
  • Empty everything from your pockets, such as your wallet, coins and keys, and put them in your carry-on rather than the bins. This will reduce handling during screening.
  • Separate any food you have for X-ray scanning. Putting it in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Southeast Massachusetts?
Cape Air is a popular carrier servicing Southeast Massachusetts. Search for a ticket to Logan Intl. Airport (BOS) and you'll have 1785 Cape Air flights a month to select from.
How can I find cheap tickets to Southeast Massachusetts?
For the best deal to Southeast Massachusetts, book well ahead of time. Also think about using Expedia's "flexible dates" feature at the top of your search results. This will display prices for nearby days. In the last seven days, was the best price for a flight to Southeast Massachusetts.
How much is a flight to Southeast Massachusetts?
In the last seven days, round-trip flights to Southeast Massachusetts sold for as little as and reached a maximum of . For one-way journeys departing from (), the lowest amount paid during this same period was .
What are the most popular airports to fly into in Southeast Massachusetts?
Book your flight to Logan Intl. Airport (BOS) and experience everything that Southeast Massachusetts has to offer. As the region's primary entry point, about 12051 flights land here each month.
When is the cheapest time to fly to Southeast Massachusetts?
Jetting off on a Tuesday, followed by a Monday, is usually the best way to score the cheapest fare. Avoid weekends if possible, because Saturday is typically the most expensive day of the week. Spend the cash you saved enjoying yourself in Southeast Massachusetts instead!
How much is a plane ticket to Southeast Massachusetts?
Fares to Southeast Massachusetts ranged from to in the last seven days. Generally, the sooner you book the better the price.
Which airlines with flights to Southeast Massachusetts employ COVID-19 cleanliness policies?
As travel restrictions start to lift, most airlines are back in business with new measures including social distancing and increased sanitization. Here's what a few 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.