Boston Vacations

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Boston skyline

Your Boston vacation

This city has bragging rights as the oldest of many things, but there’s more to Boston than first meets the eye. With a history dating back to the 17th century, the Athens of America is also home to cutting-edge museums, skyscrapers and infamous Harvard Square.

Take in the rejuvenated Boston Harbor by foot or hop a boat to the city’s islands. Watch a world-series team play baseball. Chow on fresh seafood or tour a local brewery. Marvel world-famous art collections (Museum of Fine Arts, ICA) or walk a historic trail.

Whatever you choose on your Boston vacation, let Orbitz guide you with the best time to go, top 10 highlights and insider gems.

  • For the quintessential Boston vacation, early fall delivers in every way: Gorgeous fall foliage, cool temperatures, rowing regattas -- like the nation’s largest Head of the Charles celebration -- Thanksgiving dinner and hot toddies. If you don’t mind cold temperatures and snow, visit in winter when some hotels offer deeper discounts.

    Spring is beautiful with blossoming trees, baseball at Fenway Park, Patriots Day and the annual Boston Marathon. Temperate weather is typical but often accompanied by rain through mid-June. Summers may be hot and humid, but there’s something special about a Boston summer vacation, especially over the 4th of July.

  • Boston cream pie

    Order Boston cream pie at the historic Omni Parker House, where the pie and state’s official desert was first invented.

  • Transportation

    Zip around to city hotels and landmarks on Boston’s 125-station underground "T" train system for only $2 USD (kids ride free).

  • Restaurant Week

    Come in August when more than 200 restaurants offer unique three-course prix fixe menus at a steal.

  • Self-guided walks

    Get to know Boston with popular self-guided walks of the Freedom Trail, Black Heritage Trail and Boston HarborWalk, all of which are free.

  • America's oldest restaurant

    Dine at The Union Oyster House, the oldest restaurant in continuous service in the U.S. with doors open since 1826. Enjoy New England faves like scallops, lobster, clams and scrod.

Boston Hotels

From $182

1 The Boston Park Plaza Hotel

4 stars
3.7 / 5 799 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

From $285

2 Boston Marriott Long Wharf

4 stars
4.2 / 5 83 reviews

296 State Map

Rate includes breakfast

Though only built in 1982, Boston Marriott Long Wharf hotel sits within an integral part of Boston's history and the 17th century focal point of Boston's sea trade. Emulating the warehouse-feel of the old city, the diamond structure is matched inside with the geometric... More

From $256

3 Royal Sonesta Boston

4 stars
4.1 / 5 253 reviews

40 Edwin H Land Boulevard Map

Save 25% On Your Stay

Located on the Charles River, the hotel places you directly between Boston and Harvard with quick city access in an idyllic setting. Equipped with many in-room and conference technologies, the hotel is perfect for business travelers and tourists wanting to soak up the... More

From $277

4 The Westin Boston Waterfront

4 stars
4.1 / 5 96 reviews

425 Summer Street Map

Save 25% on your stay

There are plenty of well-connected transport options in Boston, but fitness enthusiasts should take advantage of the Westin Waterfront hotel's New Balance Gear Lending Program, which saves guests the trouble of packing athletic shoes when traveling to the "Walkable City."... More

From $280

5 Nine Zero, a Kimpton Hotel

4 stars
4.5 / 5 102 reviews

90 Tremont Street Map

Save 10% on your stay

If you'll be traveling to Boston with your pet, then you'll appreciate the animal pampering the Nine Zero provides. The hotel does not have size or weight restrictions for pets; in fact, your furry friend will receive his or her own pet bowl and bed to use during your... More

From $290

6 Residence Inn Boston Downtown/Seaport

3 stars
4.5 / 5 2 reviews

370 Congress Street Map

Book early, Save big!ďż˝ Enjoy 15% Off!

Set a pace that suits you at Residence Inn by Marriott® Boston Downtown Seaport located minutes from the financial district. Whether you're with us for a few days, a few weeks, or a few months, our unique extended stay, Boston hotel will provide you with all you need.... More

From $241

7 Marlowe, a Kimpton Hotel

4 stars
4.5 / 5 121 reviews

25 Edwin H Land Blvd Map

Save 10% on your stay

The Hotel Marlowe is a AAA four diamond-rated boutique property emanating elegance and vibrancy with eclectic style throughout the space. Overlooking the Charles River, the hotel offers easy access to MIT and Harvard, as well as some of Boston's best attractions and... More

From $242

8 Renaissance Boston Waterfront Hotel

4 stars
4.2 / 5 127 reviews

606 Congress Street Map

Rate includes breakfast

The Renaissance Boston Waterfront Hotel keeps you close to a long list of entertainment and business venues, while maintaining a comfortable distance from downtown crowds. Rooms are modern, and the views are spectacular. For those new to Boston, the concierge desk is... More

From $235

9 Hyatt Regency Boston

4 stars
3.9 / 5 250 reviews

One Ave de Lafayette Map

Save 20% on your stay

Corner rooms tend to offer much more space than other guest rooms. There are other buildings nearby, so rooms on higher floors offer a better view of the city, in addition to being quieter than rooms on lower floors. Large guest parties in town for a conference,... More

From $256

10 Revere Hotel Boston Common

4 stars
4.2 / 5 60 reviews

200 Stuart Street Map

Save 20% on your stay

DISCOVER A DESTINATION THAT REDEFINES LUXURY AND PUTS ITS OWN SPIN ON THE BOSTON EXPERIENCE. JUST A SHORT BLOCK FROM BOSTON COMMONS REVERE HOTEL TAKES INSPIRATION FROM THE CITYS RICH HISTORY WHILE REVELING IN THE UNPREDICTABLE. THE DESIGN AND DECOR OF REVERE REFLECTS A... More

  • Promo Code Terms and Conditions

    50TRIP
    Book a qualifying 4+ night flight + hotel vacation package between July 24, 2015 12:00AM CT and September 30, 2015 11:59PM CT, for $1000 or more for travel between July 24, 2015 and December 31, 2015 via Orbitz and instantly receive $50 off the hotel portion of your booking through the use of the promotion code. Limit one discount per hotel room and one promotion code per booking. Discounts are not redeemable for cash for any reason. Promotion codes cannot be resold. Any attempt at fraud will be prosecuted to the fullest extent of the law. Void where prohibited, taxed or restricted. Orbitz reserves the right to change or limit the promotion in its sole discretion. Promo code not valid for Las Vegas, NV bookings.

  • Boston
  • Prudential Skywalk Observatory

    Who says you can’t sightsee and shop at the same time? Located on the 50th floor of Boston’s second tallest skyscraper, the Observatory offers a cutting-edge audio tour against 360-degree views of Boston and beyond. After a woozy, breathtaking twirl, take the elevator back down to shop at stores like Club Monaco, Sephora, Gucci and Saks.

  • Museum of Fine Arts

    Home to some of the most iconic American art collections in the world (this is Boston, after all) don't miss Paul Revere's Sons of Liberty Bowl, John Singer Sargent's The Daughters of Edward Darley Boit, and Joseph Stellas Old Brooklyn Bridge. The stunning Art of Americas Wing, new in 2010, is also worth a visit.

  • New England Aquarium

    Step inside to witness the jaw-dropping Giant Ocean Tank. This awesome, 4-story, 200-gallon centerpiece exhibit swims with sharks, stingrays, barracuda, reef-dwelling fish and more. Enjoy seals, sea lions, trainer interactions and hands-on activities at the Marine Mammal Center. Countless other exhibits reveal penguins, sea dragons, jellyfish and more.

  • The Freedom Trail

    Walk in the footsteps of America's forefathers on the 2.5-mile Freedom Trail. Highlights include Boston Common, Park Street Church, Granary Burying Ground, King's Chapel, the first public school in America, Old State House, Faneuil Hall, Paul Revere House and Bunker Hill Monument.

  • Institute of Contemporary Art

    For a twist on history, the ICA is living proof of the compelling tension between old and new. Founded in 1936, the museum re-opened in 2006 within a stunning glass and metal waterfront masterpiece. With a long-standing reputation for discovering Expressionists Edvard Munch and Cubist George Braque, the ICA’s exhibits are reliably provocative. The permanent collection includes works from Marlene Dumas, Thomas Hirschhorn and Shepard Fairey.

  • The Emerald Necklace

    Designed in 1896, Boston’s six connected public parks and waterways span from the Back Bay to Dorchester with green open spaces, rivers and ponds, bridges, monuments and wildlife. Parks include Boston Common, Public Garden, Black Bay Fens with its Victory Garden and Jamaica Pond -- a favorite among runners, dog-walkers and skippers.

  • The Boston HarborWalk

    Explore the city’s waterfront neighborhoods, downtown district and maritime industrial areas. (HarborWalk runs from Chelsea Creek to the Neponset River through East Boston, Charleston North End, downtown, South Boston, and Dorchester.) If you’re traveling by boat, hop off at boating centers and public launches connected to HarborWalk to see more of Boston Harbor.

  • The Museum of Science

    Follow the "oohs" and "ahhs" to countless exhibits, including the Elihu Thomson Theater of Electricity, the Charles Hayden Planetarium, the Mugar Omni Theater, the Gordon Current Science & Technology Center, the 3-D Digital Cinema and the Butterfly Garden.

  • The JFK Presidential Library and Museum

    Journey into the life of John F. Kennedy Jr. at this popular Boston attraction where exhibitions include the space program, the Cuban Missile Crisis, the Kennedy-Nixon Debate, the 1960s campaign and the famously sophisticated Jackie Kennedy.

  • Harvard Square

    Defined by the intersections of Massachusetts Avenue, Brattle Street, and John F. Kennedy Street in Cambridge, the Square is home to Brattle Theater, Club Passim (legendary jazz), Grendel’s Den (famous eats), and the American Repertory Theater. Make like a local genius and stop at notable bookstores like the 1882-established Harvard Coop or stroll the Harvard University campus.

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