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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $2,106, price is now CA $926 per person
CA $926
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,819, price is now CA $1,480 per person
CA $1,480
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
We had a wonderful stay at the Boston Harbor Hotel - the staff was friendly and our room excellent! Thank you!

Reviewed on Aug. 31, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,594, price is now CA $1,409 per person
CA $1,409
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.

Reviewed on Aug. 28, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,911, price is now CA $1,187 per person
CA $1,187
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
First rate hotel. Definitely a Luxury hotel stay!

Reviewed on Sep. 1, 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
Price was CA $1,456, price is now CA $956 per person
CA $956
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,329 reviews)
It’s our go-to hotel in Boston whenever we visit our son who’s a student at BU. Super convenient to everything and everywhere.

Reviewed on Sep. 1, 2025

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 which includes boating, a marina and a bay or harbour

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 $219 per night from Sep 14 to Sep 15
CA $219
CA $329 total
Sep 14 - Sep 15
includes taxes & fees
Margaritaville Resort Cape Cod
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
180 Water St, Plymouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 7 to Sep 8
CA $197
CA $261 total
Sep 7 - Sep 8
includes taxes & fees
Hotel 1620 Plymouth Harbor
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 3 to Sep 4
CA $197
CA $247 total
Sep 3 - Sep 4
includes taxes & fees
Falmouth Inn
See all 11,070 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Southeast Massachusetts

Gillette Stadium

Gillette Stadium

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

Gillette Stadium
Hyannis Harbor featuring a sunset and a bay or harbour as well as a small group of people

Hyannis Harbor

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
Cape Cod National Seashore showing general coastal views and tranquil scenes

Cape Cod National Seashore

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

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.