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Boston Vacations

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

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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.

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 $128

1 The Boston Park Plaza Hotel

4 stars
3.6 / 5 683 reviews

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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 $177

2 Omni Parker House

4 stars
4.2 / 5 422 reviews

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Save 10% on your stay

The Omni Parker House, constructed in 1927, is one of the Historic Hotels of America. The original Parker House Hotel was established in 1855, and the modern venue maintains the Parker House commitment to luxury. At Parker's Restaurant, sample Baked Boston Schrod (cracker... More

Hotel only $206

3 Hyatt Regency Boston

4 stars
4.0 / 5 257 reviews

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Save 20% on your stay

Experience the excitement of the city at Hyatt Regency Boston, our award winning upscale hotel is centrally located in downtown Boston. All 502 guestrooms feature Sealy plush mattresses with feather down beds, full bath amenities and flat screen HD cable televisions with... More

Hotel only $217

4 Hyatt Regency Cambridge

4 stars
3.7 / 5 286 reviews

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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 $149

5 Club Quarters in Boston

3 stars
4.2 / 5 412 reviews

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Club Quarters hotels provide a secure, club-inspired atmosphere in prime locations throughout the United States. Free bottled water on each floor, flat-screen TVs, and an iPod docking station make this Boston hotel comfortably modern. Listen to your favorite tracks while... More

Hotel only $132

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

Hotel only $89

7 Nantasket Beach Resort

3 stars
4.1 / 5 69 reviews

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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 $139

8 Hyatt Boston Harbor

4 stars
4.2 / 5 146 reviews

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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 $247

9 Loews Boston Hotel

4 stars
4.3 / 5 19 reviews

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Save 10% on your stay

Luxurious living, historic charm and comfortable accommodations have come together to form the foundation for the Loews Boston Hotel. Built in the 1920s, this stately limestone building was actually once home to the Boston Police Headquarters. Contemporary guest rooms,... More

Hotel only $288

10 Sheraton Boston Hotel

3 stars
4.1 / 5 174 reviews

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Save 20% on your stay

With the Sheraton brand shining in neon from the top of this soaring tower block, a look out from most Sheraton Boston Hotel windows will take in glorious scenes of the river or the city of Beantown itself. Dark wood paneling and marble floors denote a simple New England... 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.