Boston Vacations

Hotel options

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

Room 1

Ages of children at time of trip (for pricing, discounts)

Boston Flight + Hotel packages

  

Earn up to 5% on hotels and 1% on flights - It's free!

By clicking, I agree to the terms and conditions.

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 Hotels

http://www.tnetnoc.com/hotelphotos/417/10417/2241284-The-Boston-Park-Plaza-Hotel-Hotel-Exterior-1-LP.jpg
50 Park Plaza at Arlington Street Map
3.7 / 5 799 reviews
  • Save 10% on this stay
  • Save 10% on this stay
From
$182

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
$182
http://www.tnetnoc.com/hotelphotos/442/249442/2631759-Kendall-Hotel-Hotel-Exterior-1-LP.jpg
350 Main St Map
4.5 / 5 29 reviews
From
$202

The Kendall Hotel in Boston offers 73 guest rooms and 4 luxury one-bedroom suites decorated in a classic American decor with reproduction furniture and luxurious bedding and bath amenities. Our rooms are inviting, spacious and decorated to bring comfort to our guests.... More

From
$202
http://www.tnetnoc.com/hotelphotos/680/1680/2631759-DoubleTree-by-Hilton-Hotel-Boston-Downtown-Hotel-Exterior-2-LP.jpg
821 Washington Street Map
3.9 / 5 136 reviews
  • Includes bkfast for up to 4 people, free internet
  • Includes bkfast for up to 4 people, free internet
From
$199

The newly-renovated DoubleTree by Hilton Hotel Boston - Downtown offers affordable, mid-scale comfort in the heart of the Theatre District. With access to the city's top attractions, including the Freedom Trail and Newbury Street's upscale boutiques, this full-service ... More

From
$199
http://www.tnetnoc.com/hotelphotos/769/42769/2241284-The-Eliot-Hotel-Hotel-Exterior-1-LP.jpg
370 Commonwealth Ave. Map
4.5 / 5 51 reviews
From
$336

Hushed hallways lead to European-inspired suites at The Eliot Hotel in fashionable Back Bay. Steps from the boutiques and restaurants of Newbury Street, bask in the warmth and comfort found in every nook of this traditionally elegant and romantic hotel. Two award-winning... More

From
$336
http://www.tnetnoc.com/hotelphotos/576/11576/2241284-Seaport-Boston-Hotel-Hotel-Exterior-1-LP.JPG
1 Seaport Lane Map
4.4 / 5 248 reviews
  • Advance Purchase Saving-nonrefundable
  • Advance Purchase Saving-nonrefundable
From
$272

City and harbor views, as well as close proximity to Boston's finest historic and cultural attractions, make the Seaport Boston Hotel a convenient choice. Start your day at the Aura Restaurant, which offers a large selection of breakfast items like omelets, French toast... More

From
$272
http://www.tnetnoc.com/hotelphotos/010/259010/2631759-The-Boxer-Boston-Hotel-Hotel-Exterior-2-LP.jpg
107 Merrimac Street Map
3.7 / 5 44 reviews
  • Advance Purchase Savings- nonrefundable
  • Advance Purchase Savings- nonrefundable
From
$235

  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 building which evokes a glamorous movie set. Located in the... More

From
$235
http://www.tnetnoc.com/hotelphotos/525/115525/2241284-Hotel-Commonwealth-Hotel-Exterior-1-LP.jpg
500 Commonwealth Avenue Map
4.6 / 5 77 reviews
From
$338

Boston Red Sox baseball fans might find a view of historic Fenway Park from an extra-spacious guest room at Hotel Commonwealth. Two blocks from the games, this independent Back Bay boutique hotel offers gracious service and an elegant atmosphere. Past the fresh flowers in... More

From
$338
http://www.tnetnoc.com/hotelphotos/748/190748/2631759-Hilton-Boston-DowntownFaneuil-Hall-Hotel-Exterior-2-LP.jpg
89 Broad Street Map
3.9 / 5 63 reviews
  • Bed & Breakfast
  • Bed & Breakfast
From
$247

Built in the 1920s as the city's first Art Deco skyscraper and recently undergoing a complete $10 million renovation, the Hilton Boston Financial District offers an enchanting blend of the old and the new. Winner of the AAA Four Diamond Award year after year, the hotel... More

From
$247
http://www.tnetnoc.com/hotelphotos/354/38354/2631759-Hilton-Boston-Back-Bay-Hotel-Exterior-1-LP.jpg
40 Dalton St Map
4.1 / 5 160 reviews
  • Includes parking, internet access OR breakfast
  • Includes parking, internet access OR breakfast
From
$297

Hilton Back Bay offers everything you've come to expect from a name like Hilton. Situated in the heart of the historic Back Bay, this hotel affords guests comfortable rooms with Hilton Serenity Collection bedding, a state-of-the-art fitness center, business services and... More

From
$297
http://www.tnetnoc.com/hotelphotos/225/302225/2241284-Boston-Hotel-Buckminster-Hotel-Exterior-1-LP.jpg
645 Beacon Street Map
3.6 / 5 131 reviews
  • Includes $10 Food Credit per room per night!
  • Includes $10 Food Credit per room per night!
From
$262

Built in 1897, the historic Boston Hotel Buckminster was one of the first hotels built in the Boston area. The hotel was designed by renowned architect Stanford White, who also designed the Boston Public Library as well as many of the elegant Back Bay townhouses on Beacon... More

From
$262
  • 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 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.

Sign up to receive our best deals

Get insider access to our best hotel deals, coupons and more!