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Boston Vacations

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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.

Best time to take a vacation to Boston

  • 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.

Insider tips for Boston travel

  • 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 Vacation Packages

Hotel only $149

1 The Boston Park Plaza Hotel

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Advance Purchase - Save 15%

Elegance and convenience in the heart of Boston's Back BayThis notable Back Bay hotel is a Historic Hotel of America and has long stood as an icon of this affluent neighborhood. Built as the Statler Hotel in 1927, it is within blocks of upscale shopping at Newbury Street... More

Hotel only $194

2 Omni Parker House

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Save 15% on your stay

Sleep in stately comfort at America's longest continually operating hotelThe Omni Parker House has welcomed travelers and socialites since 1855 and was listed by AAA in 2009 as one of the top 10 historic hotels. Omni Parker House is considered to be one of the longest... More

Hotel only $269

3 Hyatt Regency Boston

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Save 20% on your stay

Theater district hotel in the heart of downtown BostonThe Hyatt Regency Boston offers a luxurious stay for business and leisure travelers in a prime downtown location with easy access to the theater district, Freedom Trail and other popular attractions. The hotel's eco-... More

Hotel only $217

Upscale luxury with business conveniences on the Charles RiverThe Hyatt Regency Cambridge stands out as a beacon along the Charles River following a $15 million renovation of guestrooms and public spaces. The pyramid-shaped building lights up at night while looking out at... More

Hotel only $194

Convenient full-service hotel in the heart of downtown BostonLocated in the heart of downtown Boston, Club Quarters gives access to a host of the city's best features. From the Freedom Trail, Faneuil Hall and the Financial District to the North End, Club Quarters is in... More

Hotel only $144

Affordable accommodations near Logan Airport with easy access to BostonFour Points by Sheraton is located four miles from Logan International Airport, offering travelers a convenient and affordable lodging option with easy access to downtown Boston and nearby attractions... More

Hotel only $102

Oceanfront resort just 18 miles south of Boston and within driving distance of the historic Plymouth and Cape Cod. The Nantasket Beach Resort is a full-service resort, located in Hull, Massachusetts, just steps from the top-rated sandy Nantasket Beach. Here you can stay... More

Hotel only $173

8 Hyatt Boston Harbor

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Rate includes Free Valet Parking

Stylish Boston hotel with fine dining, gym and business amenitiesWith a location close to Boston's Logan International Airport, the HYATT Boston Harbor is popular with both holidaymakers and business visitors. Guests are within easy reach of Boston's attractions and the... More

Hotel only $239

9 Loews Boston Hotel

4 stars
4.3 / 5 14 reviews

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Save 10% on your stay

Loews Boston Hotel is one of the citys premier hotels. Housed in the former Boston Police Headquarters, the hotel is modern, but with a nod to Bostons rich history. The hotel features 225 well-appointed guest rooms decorated to maximize space and invigorate the senses. ... More

Hotel only $170

10 Sheraton Boston Hotel

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Save 20% on your stay

Modern comfort and amenities in centrally located Back Bay neighborhoodThe Sheraton Boston Hotel is situated adjacent to the Hynes Convention Center, Copley Place and the Prudential Center offering convenience for both business and leisure travelers. The hotel recently... More

Boston highlights

  • 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.