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Massachusetts Vacations

Your trip

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
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Your Massachusetts vacation

Forget cookie-cutter, pre-packaged vacations. When it comes to Massachusetts vacations, Orbitz lets you choose the flight and hotel that fits your calendar and price point. Mix and match your Massachusetts travel plans, and enjoy discounts you won't find when you book separately.

Get expert advice on Massachusetts travel
Narrow down the best hotels, attractions and activities for your lifestyle and budget. Orbitz offers free 24/7 support so you can plan your Massachusetts vacations with ease. Call a specialist anytime at 1-800-504-3248.

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See your vacation savings on the Orbitz Matrix Display. View all your flight and hotel options, and see what you can save on Massachusetts vacations when you book together. It's all you need to know in just one click.

Add activities to Massachusetts vacations
Skip those long lines, and bundle your flight and hotel vacation packages with activities ahead of time. Book tickets to sightseeing tours, sporting events and more.

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Massachusetts Vacation Packages

Hotel only $98

1 The Boston Park Plaza Hotel

4 stars
3.7 / 5 708 reviews

50 Park Plaza at Arlington Street Map

Save 10% on this stay

The Boston Park Plaza Hotel is designated as one of the Historic Hotels of America. This elegant hotel occupies a triangular block, which contributes to the unique appearance of both the exterior and the guestrooms themselves. The hotel features eight on-site restaurants... More

Hotel only $71

2 Red Roof PLUS Boston Woburn

2 stars
3.3 / 5 61 reviews

19 Commerce Way Map

Save 15% on your stay

The Newly Renovated 100 Percent Smoke-Free Red Roof Inn Boston - Woburn, MA has new Flat Screen TVs and is a pet friendly, family friendly hotel. This hotel is close to Winchester Hospital and Tufts University on I-93/I-95. The hotel is near Boston, Massachusetts and... More

Hotel only $99

3 Comfort Inn & Suites Logan International Airport

3 stars
4.0 / 5 186 reviews

85 American Legion Hwy. Map

Newly renovated hotel by Logan Airport with free breakfastComfort Inn & Suites is a multiple-award-winning, AAA three diamond-rated, green-certified hotel just a few miles from Logan International Airport offering easy access in and out of Boston. The hotel offers... More

Hotel only $101

4 Hyatt Regency Cambridge

4 stars
3.7 / 5 289 reviews

575 Memorial Dr Map

Includes buffet breakfast for up to 2 adts/2 chd

The Hyatt Regency Cambridge's distinctive pyramid stands out against the busy Boston skyline, its illuminations reflected in the Charles River at dusk. With unique amenities like a lending library and seasonal bike rentals, the hotel won the EPA's Energy Star Award and... More

Hotel only $109

5 Cape Codder Resort and Spa

3 stars
3.7 / 5 27 reviews

1225 Iyannough Road Map

The Cape Codder Resort & Spa offers comfortable Cape Cod lodging, romantic dining and family fun in amazing Indoor Wave Pool. The hotel offer hotel packages throughout the year and accommodate groups for functions, meetings or reunions. The resort can also assist in... More

Hotel only $179

6 W Boston

4 stars
4.4 / 5 59 reviews

100 Stuart Street Map

Save 25% on your stay

Chic accommodations and signature service set in hip theater districtFeaturing modern and sophisticated décor in its public spaces that perfectly compliment the beautiful glass façade of the building, W Boston is located in the heart of the theater district in Boston's... More

Hotel only $84

7 BEST WESTERN PLUS New Englander

3 stars
3.6 / 5 93 reviews

1 Rainin Road Map

Save 15% on your stay

Welcome to the BEST WESTERN PLUS New Englander! Our hotel provides a superior location, and has it all with plenty of free parking and an indoor pool for relaxing. Enjoy a free, full hot breakfast each morning that includes a buffet of hot waffles, fresh fruits and... More

Hotel only $69

8 Rodeway Inn Logan International Airport

2 stars
3.4 / 5 87 reviews

309 American Legion Highway Route 60 West Map

Save 20% on your stay

3 miles to Logan Airport. 5 miles to downtown Boston. Close to all universities and public transportation, Salem, Fenway Park, Faneuil Hall, JFK Library, Cheers Restaurant. Walk to beach. Great rates. Non-smoking hotel. Complimentary Shuttle service is available during... More

Hotel only $169

9 The Charles Hotel

4 stars
4.2 / 5 76 reviews

One Bennett Street Map

Winter Sale - Save 10% on 2 nights!

AAA four diamond renovated property in Harvard SquareSitting along the banks of the Charles River and steps from Harvard Square, the Charles Hotel acts as an extension of the storied scholastic institution. Known as Cambridge's most intellectual property, each of the... More

Hotel only $110

10 Resort and Conference Center At Hyannis

3 stars
3.4 / 5 23 reviews

35 Scudder Ave Map

Relax and rejuvenate at Cape Cods newly remodeled resort. The Resort and Conference Center at Hyannis sits on 52 beautifully landscaped acres in historic Hyannis Massachusetts. The resort is located across from the Cape Cod Melody Tent and within walking distance to... More