Massachusetts Vacations & Trips from $401

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Your Massachusetts Vacation

Our Massachusetts vacation packages provide an affordable, easy and engaging way to experience all that this exciting destination has to offer. If it's dining and culture you're after, this is the place to be. A trip to Massachusetts wouldn't be complete without exploring some of its most well-known cities, starting with Boston. A couple of the top attractions here include Fenway Park and TD Garden. Hyannis is another favorite city with Massachusetts travelers. Visitors to this destination enjoy Cape Codder Water Park and Cape Cod Inflatable Park. Expedia has everything you need when it comes to planning your Massachusetts vacation. From hotels and flights, to activities and more, we know how to curate a travel experience like no other.

Top destinations in Massachusetts

The Latest Massachusetts Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites Boston Logan Airport
Raffles Boston
The Whitney Hotel
The Inn at Hastings Park, Relais & Chateaux - Boston
Club Quarters Hotel Faneuil Hall, Boston

Where to stay in Massachusetts

Get a lay of the land and find the perfect place to stay Learn more about Massachusetts

Best Places to Vacation in Massachusetts

1. Find your perfect Boston vacation

Nantucket, Massachusetts is the perfect destination for a beach vacation. With its stunning geography, you can enjoy cocktails and dancing while taking in the beautiful views. Excursions to nearby islands and beach tours are popular activities, and you can explore the island by walking or biking. Nantucket also offers a variety of museums and ferry rides for a unique cultural experience. Whether you're looking for relaxation or adventure, Nantucket has it all. Don't miss out on the vibrant atmosphere and unforgettable experiences that await you on this charming island.

  • Travelers tend to stay 2 days in Boston

2. Experience Nantucket with a travel package

Salem, Massachusetts, is a cultural haven for travelers. With its rich history and stunning architecture, it's a perfect destination for museum enthusiasts and history buffs. The city offers a range of activities such as art tours, walking tours, and shopping. You can also indulge in delicious dining experiences and enjoy the friendly atmosphere. For those looking for a vibrant nightlife, Salem has a variety of bars to choose from. Whether you're interested in exploring museums or immersing yourself in the local culture, Salem has something for everyone.

  • The peak season is from June to August
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Nantucket

3. Create memories in Provincetown with a vacation package

Cambridge, Massachusetts is an ideal destination for a family vacation. With its proximity to prestigious universities, museums, and urban attractions, there's plenty to explore. Take a leisurely stroll along the picturesque river, visit world-renowned museums, and marvel at the stunning architecture. For the active family, there are ample opportunities for sports and running. Cambridge also offers a diverse dining scene, perfect for trying out different cuisines. And if you're in the mood for shopping, you'll find a variety of boutiques and shops to browse. Whether you're interested in art, academia, or simply enjoying the local atmosphere, Cambridge has something for everyone.

  • The peak season is from June to August
  • The off-peak season is from November to January
  • Travelers tend to stay 3 days in Provincetown

4. Discover Salem with our vacation deals

Provincetown, located in Massachusetts, offers a unique and diverse atmosphere for outdoor vacation seekers. With its proximity to the ocean, visitors can indulge in delicious seafood and relax on beautiful beaches. The town is also known for its biking trails, providing an opportunity to explore the picturesque surroundings. Provincetown is a small town with a vibrant entertainment scene, boasting theaters and art galleries. It is renowned for being LGBTQ+ friendly, creating a welcoming environment for all travelers. Birdwatching enthusiasts will be delighted by the variety of species found in the area. The town's historic port and monuments offer a glimpse into its rich maritime history, while boating excursions provide an adventurous experience. Whether you're looking for relaxation, entertainment, or outdoor exploration, Provincetown has something for everyone.

  • The peak season is from August to October
  • The off-peak season is from November to January
  • Travelers tend to stay 2 days in Salem

6. Book your ideal Hyannis with a vacation package

Chatham, located in Massachusetts, offers a charming coastal atmosphere perfect for a beach vacation. With its proximity to the sea and port, visitors can enjoy fresh seafood, fishing excursions, and breathtaking sunsets. The town is also known for its trendy shops and vibrant art scene. For sports enthusiasts, Chatham is home to a popular baseball team. However, it's important to note that the area is also known for its shark sightings. Overall, Chatham provides a unique and diverse experience for travelers looking to relax and enjoy the beauty of the beach.

  • The peak season is from June to August
  • The off-peak season is from November to January
  • Travelers tend to stay 2 days in Hyannis

5. Enjoy Cambridge with a travel package

Hyannis, located in Massachusetts, is an ideal destination for a beach vacation. With its proximity to the ocean, visitors can indulge in seafood delicacies and enjoy activities like ferry rides, shopping, and dining. The port area offers opportunities for boating and sports, while the beaches provide a relaxing atmosphere for sunbathing and swimming. Excursions and cafes are also popular among travelers. Whether you're looking for a day at the beach or exploring the local attractions, Hyannis has something to offer for everyone.

  • The peak season is from March to May
  • The off-peak season is from November to January
  • Travelers tend to stay 2 days in Cambridge

Find the Best Massachusetts Vacation Packages

Massachusetts Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Top Sights
New England Aquarium, Boston Common and Cape Cod National Seashore

Massachusetts Hotel Deals

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $120 total per night from Nov 23 to Nov 24
$120 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (2,193 reviews)
Nice service. But the shawer Water is not hot enough.

Reviewed on Oct 29, 2025

The Revolution Hotel
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $236 total per night from Nov 24 to Nov 25
$236 total
Nov 24 - Nov 25
Total with taxes and fees
9.4/10 Exceptional! (6,638 reviews)
Very clean and friendly staff. We LOVED the sweet little man in the hat that greeted us each day and asked if we needed help with our bags! Was a bit noisy throughout the night but was outside noise, street sweepers, honking cars etc. not hotels fault.

Reviewed on Oct 28, 2025

The Dagny Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $208 total per night from Nov 27 to Nov 28
$208 total
Nov 27 - Nov 28
Total with taxes and fees
9/10 Wonderful! (4,199 reviews)
About to check in at 11am, no charge.

Reviewed on Oct 27, 2025

Omni Boston Hotel at the Seaport
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.

Frequently asked questions

How much does a Massachusetts vacation package cost?
Explore the best of Massachusetts from as low as $401. Choose from a wonderful selection of flights, rental cars and hotels to suit every budget. Score even better deals when you add some tours or activities to your package.
How do I get a cheap travel package to Massachusetts?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got it all. Pick a combination that best fits you and watch your savings pile up. We know a package deal is never a one-size-fits-all. That's why Expedia offers over 550 airlines and 1,000,000 hotel options throughout the world, which lets you customize your Massachusetts getaway.
Where should I stay in Massachusetts?
To explore fantastic attractions like Fenway Park and TD Garden, Boston is the place to be. Many travelers also rave about Plymouth, home to Plymouth Rock and National Monument to the Forefathers. If you've got an extended vacation in Massachusetts, why not visit both cities?
What are the top hotels in Massachusetts?
Check out Hampton Inn Boston - Logan Airport and The Dagny Boston. They're top picks for many travelers headed to Boston. If Provincetown is on your itinerary, Copley Square Hotel, a FOUND Hotel and Hilton Boston Park Plaza are a couple of popular options.
How far in advance should I book my Massachusetts vacation?
Savvy travelers often book as early as possible. You can normally compare international airfares on Expedia up to a year before your intended flight. If you've left things to the last minute, don't stress. Low prices sometimes appear just weeks before departure.
What does an Expedia Massachusetts travel package include?
You can choose from any combination of flights, hotels and rental cars. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to organizing your ideal Massachusetts trip.
What should I know before booking a Massachusetts travel package?
You'll save plenty with an Expedia travel package. Bundle your airfares, rental cars and hotels and land exciting discounts. Hotels aren't your only option, though. We have beachside villas, rural cottages and even ranches and treehouses!
Can I choose my airline with a Massachusetts Expedia vacation package?
You sure can. We offer more than 550 partner airlines across the globe, so select the carrier that fits your needs.
Does Expedia offer Book Now, Pay Later Massachusetts vacation packages?
Your bank balance shouldn't prevent you from having a fabulous vacation, so Expedia has devised a plan to help. Thanks to our partnership with online lender Affirm, it's easier than ever to book the perfect getaway that won't drain your wallet. Simply Book Now, Pay Later and take the financial strain out of planning for your journey.
If I'm not able to travel, can I cancel my Massachusetts vacation package?
You can cancel your Massachusetts booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

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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.