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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,379, price is now CA $901 per person
CA $901
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (189 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year

Reviewed on Jun 18, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,154, price is now CA $1,883 per person
CA $1,883
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $2,645, price is now CA $1,753 per person
CA $1,753
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (713 reviews)
Property is located on the beach, and that’s a huge plus. Rooms are clean, and the staff was pleasant to deal with. I met fellow travelers that book the same room on the same weeks for many years in a row, and that should tell you something.

Reviewed on Jun 23, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $1,491, price is now CA $1,012 per person
CA $1,012
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (150 reviews)
New and well presented hotel in a great location to access Cambridge and Boston

Reviewed on Jun 23, 2026

Ashworth by the Sea

Ashworth by the Sea

3 out of 5
Hampton Beach
Price was CA $2,482, price is now CA $1,775 per person
CA $1,775
per person
Jul 26 - Aug 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (1,345 reviews)
Access and location to beach was great and staff was helpful. Elevator did not work, fridge in room would not get cold, water never turned hot and had to ask for refill for shampoo and conditioner.

Reviewed on Jun 25, 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
Nantucket Town

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

Garner Hotel Brockton - Boston by IHG

Garner Hotel Brockton - Boston by IHG

2.5 out of 5
405 Westgate Dr. Brockton MA
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Jul 12 to Jul 13
CA $153
CA $170 total
Jul 12 - Jul 13
includes taxes & fees
8.4/10 Very good! (1,041 reviews)
"Great hotel"

Reviewed on Jun 24, 2026

Garner Hotel Brockton - Boston by IHG
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 $382 per night from Jul 6 to Jul 7
CA $382
CA $519 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (600 reviews)
"Outdoor pool was closed and so was the hot tub. Small water area, pool and slides are for young kids. I’ll stick with Great Wolf Lodge from now on."

Reviewed on Jun 24, 2026

Margaritaville Resort Cape Cod
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Jul 1 to Jul 2
CA $221
CA $253 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (267 reviews)
"I did not use the amenities. The breakfast was nice. It was a comfortable, safe, clean place, good value for the dollar."

Reviewed on Jun 23, 2026

Iris Hotel Cape Cod
See all 11,710 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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Stay near popular Southeast Massachusetts attractions

Photo by The Curious Zephyr
Open Photo by The Curious Zephyr

Gillette Stadium

9.0/5 (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

What to do in Southeast Massachusetts

Moby Dick's New Bedford Smartphone Guided Walking Tour

Moby Dick's New Bedford Smartphone Guided Walking Tour

CA $11
per adult
Moby Dick's New Bedford Smartphone Guided Walking Tour
See all activities in Southeast Massachusetts

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.