Deals on vacations and trips to Massachusetts

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Boston Common featuring a monument, a city and a statue or sculpture

Boston

Vacations
Boston

Massachusetts flight + hotel vacation packages

The Boxer

The Boxer

4 out of 5
West End
Price was $760, price is now $575 per person
per person
Oct 27 - Oct 29
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Business travelers can take advantage of the business center. Express check-in, express check-out, and a computer station are also on offer.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flightPrice was $1,228, price is now $974 per person
per person
Oct 26 - Oct 29
Roundtrip non-stop flight included
San Francisco (SFO) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flightPrice was $1,033, price is now $820 per person
per person
Oct 27 - Oct 29
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flightPrice was $1,116, price is now $911 per person
per person
Oct 27 - Oct 29
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
Government Center
Price was $597, price is now $493 per person
per person
Oct 27 - Oct 29
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.
Prices and availability subject to change. Additional terms may apply.

Top Massachusetts hotels deals

Boston Park Plaza

Boston Park Plaza

4 out of 5
50 Park Plaza at Arlington Street, Boston, MA
Free Cancellation
Reserve now, pay when you stay
The price is $244 per night
$244
per night
Oct 9 - Oct 10
This historic hotel's 2 restaurants, 3 bars/lounges, and gym are some of the featured amenities. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi. Valet parking, a 24-hour business center, and a garden are also offered.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4.5 out of 5
450 Summer Street, Boston, MA
Free Cancellation
Reserve now, pay when you stay
The price is $287 per night
$287
per night
Sep 28 - Sep 29
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
The price is $208 per night
$208
per night
Oct 9 - Oct 10
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.
The Arcadian powered by Sonder

The Arcadian powered by Sonder

3.5 out of 5
1200 Beacon St, Brookline, MA
The price is $188 per night
$188
per night
Oct 1 - Oct 2
Free WiFi in public areas and luggage storage are available at this hotel. Staff at the 24-hour front desk can provide around-the-clock assistance.
Copley Square Hotel

Copley Square Hotel

4 out of 5
47 Huntington Ave, Boston, MA
Free Cancellation
Reserve now, pay when you stay
The price is $275 per night
$275
per night
Oct 9 - Oct 10
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, express check-out, and luggage storage are also offered.
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
Free Cancellation
Reserve now, pay when you stay
The price is $322 per night
$322
per night
Oct 15 - Oct 16
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a grocery/convenience store, and a library are also on offer.
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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.

Popular places to visit

Image for Fenway Park

Fenway Park

4.5/5(2,499 reviews)

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

4.5/5(1,966 reviews)

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 Boston Common

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Frequently asked questions

How much are vacation packages to Massachusetts?
With deals starting at just $493, hotel and flight packages are a superb way to stretch your travel budget. Massachusetts, here you come!
Where can I get the best vacation package deals for Massachusetts?
You can pick up awesome Massachusetts package deals with Travelocity. Pick and choose from as many as 400 partner airlines and 1,000,000 worldwide properties and turn your travel dreams into reality.
Why should I purchase my Massachusetts vacation bundle via Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you can rest easy knowing you’ll always get the best deal available.
Can I save on my Massachusetts car rental if I bundle it with a hotel or flight?
Bundling your bookings into a Massachusetts vacation package will leave you with some serious savings. You can combine a car and flight; a car, hotel and flight; or a car and hotel. There’s no better way to explore the greater Massachusetts area than with your own set of wheels. You can also add activities and experiences to your Travelocity package.
What is the best time of year to go to Massachusetts?
If you want to avoid costly airfares, crowds and full hotels, organize your getaway outside of June, July and August. The quietest time to travel to Massachusetts is November, December and January. You’ll find hotel rates are the highest in and the most affordable in .
Which airport is best for Massachusetts?
For anyone journeying to and from Massachusetts, the most popular airports are Logan Intl. Airport (BOS), T.F. Green Airport (PVD) and Manchester-Boston Regional Airport (MHT).
What is there to do in Massachusetts?
Massachusetts has hidden surprises around every turn, but make sure you plan a trip to Fenway Park and Boston Common while you’re in town. These two attractions can’t be missed.

Where to stay in Massachusetts: Best areas for travelers