Massachusetts Vacations & Trips

Choose one or more items to build your trip:
Choose one or more items to build your trip:

Top destinations in Massachusetts

  • Boston Common featuring a monument, a city and a statue or sculpture
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    Boston
    Boston
  • Plymouth featuring shopping
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    Plymouth
    Plymouth
  • Nantucket which includes cbd, boating and a small town or village
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    Nantucket
    Nantucket
  • Hyannis showing a marina and a bay or harbor
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    Hyannis
    Hyannis
  • Springfield featuring night scenes, a high rise building and skyline
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    Springfield
    Springfield
  • FlightsFlightsHotelsHotels
    Gloucester
    Gloucester
  • FlightsFlightsHotelsHotels
    Oak Bluffs
    Oak Bluffs

Massachusetts Flight and Hotel Deals

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Theatre District
Price was $3,536, price is now $2,230 per person
per person
Nov 7 - Nov 13
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
4.4/5 Excellent! (251 reviews)
I was transferred to this property after a horrible experience at a nearby hotel. The Ritz gave me a beautiful room with a beautiful view, it was cleanly and the staff were so sweet. 10/10

Reviewed on Jul 29, 2022

Freepoint Hotel Cambridge, Tapestry Collection by Hilton

Freepoint Hotel Cambridge, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flightPrice was $644, price is now $470 per person
per person
Dec 12 - Dec 16
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
4.2/5 Very Good! (1,001 reviews)
Good hotel but overpriced for the amenities and the environment

Reviewed on Sep 25, 2022

Holiday Inn Express & Suites Boston - Cambridge, an IHG Hotel

Holiday Inn Express & Suites Boston - Cambridge, an IHG Hotel

2.5 out of 5
East Cambridge
Save 100% on your flightPrice was $543, price is now $446 per person
per person
Dec 12 - Dec 16
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
4.2/5 Very Good! (999 reviews)
Staff was friendly and helpful. Breakfast was good. Room was clean.

Reviewed on Sep 14, 2022

Aloft Boston Seaport District, a Marriott Hotel

Aloft Boston Seaport District, a Marriott Hotel

3 out of 5
Seaport District
Price was $548, price is now $452 per person
per person
Nov 2 - Nov 4
Roundtrip flight included
Miami (MIA) to Boston (BOS)
4.4/5 Excellent! (1,000 reviews)
Aloft is always comfortable, easy and convenient. The location is accessible to everywhere and staff are very accommodating.

Reviewed on Sep 26, 2022

Staybridge Suites Boston Logan Airport - Revere, an IHG Hotel

Staybridge Suites Boston Logan Airport - Revere, an IHG Hotel

3 out of 5
Price was $491, price is now $414 per person
per person
Dec 12 - Dec 16
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
4.5/5 Wonderful! (276 reviews)
The only problem with this property is that you have to pay for parking. Why do I have to pay for parking for where I paid to stay.

Reviewed on May 30, 2022

Where to stay in Massachusetts

Find the best Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Massachusetts
  • Downtown Boston which includes night scenes and a city as well as a small group of people

    Downtown Boston

    2 out of top 10 points of interest in this area

    4.5/5Wonderful!(2,415 area reviews)

    The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

    Find hotel + flight trips in Downtown Boston
  • Back Bay featuring a city, heritage architecture and street scenes

    Back Bay

    1 out of top 10 points of interest in this area

    4.5/5Wonderful!(3,595 area reviews)

    Parisian boulevards and elegant brownstones conjure a truly romantic atmosphere, perfect for strolling and window shopping.

    Find hotel + flight trips in Back Bay
  • Seaport District which includes a city, a river or creek and a high rise building

    Seaport District

    4.5/5Wonderful!(1,075 area reviews)

    Join excited crowds enjoying harbor-side views, Revolutionary War-era landmarks, as well as superb restaurants and museums along this thriving waterfront.

    Find hotel + flight trips in Seaport District
  • Boston Harbor which includes performance art, music and a bay or harbor

    North End

    4.5/5Wonderful!(330 area reviews)

    An eventful Revolutionary history combines with Italian culture and cuisine to form one of Boston’s most exciting neighborhoods, a great first stop for a city visit.

    Find hotel + flight trips in North End
  • Kenmore Square showing street scenes

    Fenway–Kenmore

    2 out of top 10 points of interest in this area

    4.5/5Wonderful!(826 area reviews)

    Art galleries, museums, and historic sites highlight some notable features of Fenway–Kenmore. Make a stop by Fenway Park or Isabella Stewart Gardner Museum while you're visiting, and jump aboard the metro at Museum of Fine Arts Station or Fenway Station to get around town.

    Find hotel + flight trips in Fenway–Kenmore

Massachusetts Hotel Deals

Copley Square Hotel
Copley Square Hotel
4 out of 5
47 Huntington Ave, Boston, MA, 02116
Fully refundableReserve now, pay when you stay
The price is $208 per night from Oct 30 to Oct 31
4/5 Very Good! (1,009 reviews)
"easy check in. clean, friendly staff. was expecting room service and a bar but this area was under construction. i think they need to charge less per day for this inconvenience."

Reviewed on Sep 29, 2022

The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA, 02116
Fully refundableReserve now, pay when you stay
The price is $215 per night from Oct 31 to Nov 1
4.2/5 Excellent! (1,058 reviews)
"The parking is about 3-4 blocks away (and $30 per day) which was inconvenient but the hotel itself is great."

Reviewed on Sep 28, 2022

Hampton Inn Boston - Logan Airport
Hampton Inn Boston - Logan Airport
2.5 out of 5
230 Lee Burbank Hwy, Revere, MA, 02151
Fully refundableReserve now, pay when you stay
The price is $215 per night from Oct 30 to Oct 31
3.9/5 Good! (2,621 reviews)
"Every 30 min free shuttle to the airport or car rentals. Free breakfast. This is a new hotel, very clean, with all basic needs. Pricey for 2.5 star, but very nice."

Reviewed on Sep 29, 2022

See all 13234 properties in 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.

Frequently asked questions

How much does a Massachusetts vacation package cost?
Discover the best of Massachusetts from as low as $414. Choose from a great selection of rental cars, hotels and flights to suit every budget and style. Land even better deals when you add a couple of tours or activities to your vacation package.
If I'm not able to travel, can I cancel my Massachusetts vacation package?
Whether it’s your hotel, flight or rental car, yes, you can cancel or amend it. Locked in your Massachusetts vacation package in the last 24 hours? You may be able to make changes at no cost. For older bookings, you may incur a charge from your hotel, airline or car rental company. For more details, check out our Customer Service Portal. We’re here to help you every step of the way.
How do I get a cheap travel package to Massachusetts?
You can save up to $366 if you combine your car rentals, hotels and flights into a Massachusetts travel package. Sometimes cheap means fewer options. But not with Expedia. We offer over 550 partner airlines and 1,000,000 properties across the world, which means you’ll always have plenty of variety to choose from. Eager to save even more? Add some fun activities to your package deal and unlock even more discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Massachusetts?
To see famous attractions like Fenway Park and Boston Common, Boston is where you need to be. Lots of travelers also adore Provincetown, home to Pilgrim Monument and Herring Cove Beach. If you’ve got an extended vacation in Massachusetts, why not check out both cities?
What are the top hotels in Massachusetts?
Take a look at Boston Park Plaza and Embassy Suites Boston Logan Airport. They’re top picks for lots of travelers to Boston. If Provincetown is on your travel itinerary, Harbor Hotel Provincetown and Surfside Hotel and Suites are two great options.
When is the best time of year to visit Massachusetts?
Massachusetts is very popular in . If you’re not fond of big crowds and prefer a calmer pace, book your trip for . Watching your vacation finances? Take advantage of the cheap deals on offer in . is typically when prices go up and hotel rates are at their peak.
How far in advance should I book my Massachusetts vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can generally browse through international airfares on Expedia up to 12 months before your intended flight. If you’re booking last minute, don’t stress. Cheap prices occasionally occur in the last weeks prior to departure.
What does an Expedia Massachusetts travel package include?
It’s up to you! You can select from a variety of Massachusetts packages, such as a rental car, flight and hotel. You can also book a flight with a hotel, or a rental car with a flight. Once you’ve made your booking, you can add on the fun stuff like tours and activities. Whatever your perfect Massachusetts trip looks like, get set to save!
What should I know before booking a Massachusetts travel package?
Find deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we’re a one-stop shop for all of them. You’ll save precious cash just for combining your bookings. Whether you’re going on a snow and ski adventure or sipping cocktails on a beach, your perfect vacation is only a few clicks away.
Does Expedia offer Book Now, Pay Later Massachusetts vacation packages?
If you’re aching to see the world but aren’t able to pay full price, Expedia can lend a hand with a custom payment option. Thanks to our partnership with online lender Affirm, you can Book Now, Pay Later and start planning your journey today.
Can I choose my airline with a Massachusetts Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to choose from around the globe. With so many choices, finding the perfect carrier to whisk you off to Massachusetts will be a breeze.
Can I travel to Massachusetts right now?
Our Covid-19 Travel Advisor is the place to find up-to-date information regarding quarantine policies and travel restrictions for Massachusetts. Get clued up before you take off!

Popular places to visit

Image for Fenway Park

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Image for Harvard University

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Image for Copley Square

Copley Square

Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax.

Copley Square

Things to do

Image for Boston Old Town Trolley Hop-on Hop-Off City Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

$66
Per adult
88% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Image for Go City: Boston All-Inclusive Pass with 40+ Attractions

Go City: Boston All-Inclusive Pass with 40+ Attractions

$69
Per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 40+ Attractions
Image for History & Hauntings of Salem Guided Walking Tour

History & Hauntings of Salem Guided Walking Tour

$32
Per adult
98% of travellers recommend
History & Hauntings of Salem Guided Walking Tour
See all activities in Massachusetts

More trip options