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.
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
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.
Downtown Nantucket
If you're spending some time in Downtown Nantucket, Nantucket Atheneum and Nantucket Ferry Terminal are top sights worth seeing.
West of Town
While visiting West of Town, you might make a stop by sights like Nantucket Historical Association and Loines Observatory.
Katama
While visiting Katama, you might make a stop by sights like South Beach and Norton Point Beach.
New Seabury
Travelers like the museums in New Seabury, and South Cape Beach State Park is a top attraction you might want to visit.
Ready to book your vacation to Southeast Massachusetts?
Southeast Massachusetts Hotel Deals
Best Western Adams Inn Quincy-Boston
29 Hancock St Quincy MA
Fully refundableReserve now, pay when you stay
CA $252
CA $281 total
Sep 28 - Sep 29
includes taxes & fees
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
CA $189
CA $297 total
Oct 25 - Oct 26
includes taxes & fees
8.6/10 Excellent! (775 reviews)
"Un muy buen lugar, perfecto en todas las estaciones del año, aquí hay mucha diversión"
Reviewed on Sep 23, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
CA $187
CA $214 total
Oct 12 - Oct 13
includes taxes & fees
8.4/10 Very good! (399 reviews)
"Clean room and friendly staff. Very good breakfast. Elevator made it very easy to access 2nd floor rooms."
Reviewed on Sep 23, 2026
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.
Stay near popular Southeast Massachusetts attractions
Photo by The Curious Zephyr
Gillette Stadium
9.0/10 (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.
Cape Cod National Seashore
9.6/10 (1,134 reviews)
Covering over miles of shoreline around Cape Cod, this national park offers endless things to see and do regardless of the season.
Photo by Elizabeth Sanders
Mayflower Beach
9.2/10 (224 reviews)
Why not spend a carefree afternoon at Mayflower Beach during your travels in Dennis? While you're in the area, stroll along the waterfront.
Inkwell Beach
9.0/10 (154 reviews)
If a restful vacation is part of your travel plans, Inkwell Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront, or simply enjoy its wineries.
Plymouth Rock
8.6/10 (1,102 reviews)
No American historical tour is complete without a personal encounter with this symbol of national identity and origins.
Photo by Jennywisearcade
Commercial Street
9.6/10 (523 reviews)
Enjoy a stop at Commercial Street, an entertaining place to visit in Provincetown. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
Xfinity Center
8.4/10 (299 reviews)
You can make plans for a show at Xfinity Center on your trip to Mansfield. Experience the area's acclaimed theater scene or attend a sporting event.
What to do in Southeast Massachusetts
Moby Dick's New Bedford Smartphone Guided Walking Tour
CA $11
per adult
Frequently asked questions
How much does a Southeast Massachusetts vacation package cost?
Starting from a low CA $1,066, 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.
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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.
