Southeast Massachusetts Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Location is perfect. A lots of places to see within walking distance and good restaurants nearby too. The service is great. Friendly and professional staff. The room is clear and spacious. The gym is very big with all the equipments and have personal training rooms too. We stayed 5 nights and were very lucky to get room on 16th floor with a balcony!

Reviewed on Jul. 14, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,009 reviews)
We booked through Expedia. They charge rooms that booked through discount sites an “urban fee of $35 per night for your convenience”. Whether you want something or not, you are charged an additional $35 and this is only for rooms that book with a discount rate. We were given a room with no working refrigerator- they brought a banged up one up and it was placed in the room randomly. We were not able to access a movie which was part of their “urban deal”. Phone to concierge either wasn’t working or no one was answering around 9:30 pm so had to get redressed and head downstairs to ask a question. It’s a beautiful hotel and the people behind the scenes were so kind but we were definitely treated like reduced rate guests.

Reviewed on Jul. 14, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Beautiful, spacious, kind and attentive staff. Great location. Room was lovely.

Reviewed on Jul. 12, 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 a marina, boating and a bay or harbor

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

Ready to book your vacation to Southeast Massachusetts?

 

Choose your dates

Southeast Massachusetts Hotel Deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane, Nantucket, MA
The price is CA $715 per night from Jul 27 to Jul 28
CA $715
CA $799 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (484 reviews)
"Great"

Reviewed on Jul. 8, 2025

Nantucket Inn
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 $270 per night from Jul 24 to Jul 25
CA $270
CA $309 total
Jul 24 - Jul 25
includes taxes & fees
8/10 Very Good! (45 reviews)
Did the trick
"Clean room, building and rooms are a bit dated. Would return, fairly priced."

Reviewed on Jul. 13, 2025

Iris Hotel Cape Cod
Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Jul 16 to Jul 17
CA $176
CA $202 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very Good! (1,013 reviews)
"Close to many things. Walls are thin but can deal with it"

Reviewed on Jul. 14, 2025

Cape Sands Inn
See all 11,330 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

4.5/5(27 reviews)

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

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
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

Frequently asked questions

How much does a Southeast Massachusetts vacation package cost?
Starting from a low CA $798, a package is your gateway to inexpensive travel. Custom build your Southeast Massachusetts adventure by selecting from our comprehensive range of airfares, hotels and rental cars.
How do I get a cheap travel package to Southeast Massachusetts?
One word: bundle. Flights, rental cars and hotels --- combine whatever you need into a Southeast Massachusetts vacation package and save. Score even better deals when you include extras such as activities or tours to your booking. But that's not the only impressive part. You have the freedom to customize your trip your way. We offer over 550 airlines and 1,000,000 hotel options in all corners of the globe, so that everyone has a chance to travel and fulfill those vacation fantasies.
Where should I stay in Southeast Massachusetts?
Plymouth is a fantastic place to include in your itinerary. It's where you'll find well-known sights including Plymouth Rock and Mayflower II. Provincetown also draws in many wanderers eager to explore some of the best attractions in Southeast Massachusetts. Two of the best are Pilgrim Monument and Herring Cove Beach.
What are the top hotels in Southeast Massachusetts?
When it comes to hotels in Provincetown, Hampton Inn Boston - Logan Airport and Boston Park Plaza are two terrific options. If you're also visiting Brewster, 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 Southeast Massachusetts vacation?
While not all air carriers release tickets early, customers are usually able to start comparing international fares on Expedia up to a year in advance. This is the time you'll score some fantastic deals. If you're booking late, you could still be in luck. Discounted prices occasionally emerge a few weeks prior to departure.
What does an Expedia Southeast Massachusetts travel package include?
Flights, rental cars and hotels --- you'll find them all here. With Expedia, you can shape your Southeast Massachusetts package the way you want. All you have to do is decide exactly what you need. Once you've made your booking, you can add extras like activities and tours. The more you bundle, the greater your savings!
What should I know before booking a Southeast Massachusetts travel package?
Bundling your bookings into a Southeast Massachusetts vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Southeast Massachusetts Expedia vacation package?
Yes --- that's one of the best things about an Expedia package. You're the boss! We have more than 550 partner airlines all over the world, so you have options galore when arranging your Southeast Massachusetts adventure.
If I'm not able to travel, can I cancel my Southeast Massachusetts vacation package?
You can. We understand that life doesn't always go to plan, so we're happy to help if you have to make changes to your Southeast Massachusetts vacation package. You may be able to cancel or change your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

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.