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 Vacation Packages

Hotel only $128

1 The Boston Park Plaza Hotel

4 stars
3.7 / 5 818 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 $159

2 Holiday Inn Express & Suites BOSTON GARDEN

3 stars
3.3 / 5 57 reviews

280 FRIEND STREET Map

Welcome to the Holiday Inn Express Hotel and Suites Boston Garden The hotel is located across from North Station and the TD Bank Garden making it the closest hotel to the Garden, home to both the Boston Celtics and the Bruins. Boston is a walking city and the hotel is... More

Hotel only $157

3 The Boxer Boston Hotel

3 stars
3.5 / 5 43 reviews

107 Merrimac Street Map

Advance Purchase Savings- nonrefundable

A taste of 19th century grandeur in the heart of Boston  Lovers of stylish architecture should head straight for The Boxer Hotel. Constructed in the triangular flatiron style popular in many East Coast cities, The Boxer Hotel is a fully restored 19th century... More

Hotel only $220

4 Nine Zero, a Kimpton Hotel

4 stars
4.5 / 5 98 reviews

90 Tremont Street Map

Save 10% on your stay

The Nine Zero is a superior boutique hotel in Boston that offers renowned hospitality from the Kimpton Company. The hotel's exterior is constructed from traditional red brick, and the rooms feature stylish yet comfortable design elements. Guests of the Nine Zero will... More

Hotel only $179

5 Hyatt Regency Boston

4 stars
4.0 / 5 267 reviews

One Ave de Lafayette Map

Save 20% on your stay

The Hyatt Regency Boston hotel offers modern amenities in the historic heart of Boston. Large windows offer spectacular views of the waterfront and the dome of the Massachusetts State House, allowing guests some of the city's best sights without having to leave their... More

Hotel only $198

6 The Westin Copley Place, Boston

4 stars
4.3 / 5 118 reviews

10 Huntington Avenue Map

Save 15% on your stay

The Westin Copley Place Boston Hotel provides its guests with a relaxing experience in the midst of one of America's most exciting cities. It is situated right next to Copley Place-a premier shopping destination-and within walking distance of many of Boston's most popular... More

Hotel only $209

7 W Boston

4 stars
4.4 / 5 67 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 $255

8 Lenox Hotel

4 stars
4.6 / 5 242 reviews

61 Exeter St Map

The Lenox Hotel is designated as one of the Historic Hotels of America, as well as being an outstanding' green' venue with sustainability practices and recycling initiatives. Since 1900, luxurious European-themed accommodations have hosted rich and famous guests,... More

Hotel only $169

9 Marlowe, a Kimpton Hotel

4 stars
4.5 / 5 125 reviews

25 Edwin H Land Blvd Map

Save 10% on your stay

Award-winning luxury boutique hotel overlooking the Charles RiverThe 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... More

Hotel only $199

10 Boston Marriott Cambridge

3 stars
4.3 / 5 118 reviews

Two Cambridge Center Map

Rate includes breakfast

Explore historic Cambridge from the modern comfort and convenience of the Boston Marriott Cambridge. Located steps away from the popular Kendall Square, our hotel is situated next to the city's top shopping, dining, and entertainment venues, and offers superb access to... More

  • Promo Code Terms and Conditions

    150VACA
    Book a qualifying 4-night flight + hotel vacation package between January 1, 2014 12:00AM CST and June 30, 2015 11:59PM CST, for $1000 or more for travel between January 1, 2014 and September 30, 2015 via Orbitz and instantly receive $150 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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