Southeast Massachusetts Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Four Seasons Hotel Boston
Bay Village
CA $2,525
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (475 reviews)
It was our first visit to Boston. So glad we stayed at the Four Seasons on Boylston. It’s centrally located to all the attractions that were on our list. The city view trolley is located across the street from the hotel. Easy hop on and off. Staff were amazing - friendly and professional. We will definitely stay here again when we come back to Boston.
Reviewed on Aug 6, 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
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 Whaling Museum are top sights worth seeing.
Bass River
Estuary village Bass River offers kiteboarding at West Dennis Beach, windsurfing at Kalmus Beach, and attractions like Marsh Island and Windmill Beach. Enjoy a round at Bass River Golf Course too!
West of Town
While visiting West of Town, you might make a stop by sights like Nantucket Historical Association and Loines Observatory.
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
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
CA $248
CA $363 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (675 reviews)
"Clean room, family friendly and quiet!"
Reviewed on Aug 9, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
CA $190
CA $217 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very good! (330 reviews)
"Check in was easy and staff was friendly. Rooms were okay, the floors weren’t cleaned well but the bed was comfy."
Reviewed on Aug 9, 2026
Sonesta Select Boston Foxborough Mansfield
35 Foxborough Boulevard Foxborough MA
Fully refundableReserve now, pay when you stay
CA $149
CA $167 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (1,047 reviews)
"Everyone was very nice, bar in the lobby was open until 1, the gym was open all times, the pool was clean, We were at a concert in the area and they had the artists music playing which was a nice touch. Breakfast included but also had a starbucks right next door"
Reviewed on Aug 9, 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 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.
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.
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 $1,074, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
