Pinehurst Vacations from $501

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Your Pinehurst Vacation

When a getaway to the city is calling, answer it with a vacation package to Pinehurst. The neighborhood of Ballardvale, which is great for watersports, nature and history, makes a fantastic base for your adventures. A trip to Pinehurst is a terrific opportunity to take in the sights. Make sure you visit well-known attractions like Clara Sexton House, Nutting Lake Conservation Land and Country Club of Billerica. Browse Expedia's extensive range of travel options and begin planning your perfect vacation to Pinehurst now.

The Latest Pinehurst Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.
    Jan 15 - Jan 18

    Iris Hotel Cape Cod + Flight

    Falmouth
    3 nights
    3.0 star property
    8.4/10 - Very good (437 reviews)
    Roundtrip • Miami (MIA) - Boston (BOS)
    MIA - BOS • Nonstop BOS - MIA • Nonstop
    $847
    $501
    per traveler
    found 22 hours ago
    Iris Hotel Cape Cod
  • A modern kitchen with white cabinets, stainless steel appliances, and a dining area set for four.
    Dec 21 - Dec 26

    Boston Lodge and Suites + Flight

    Dorchester
    5 nights
    4.0 star property
    8.4/10 - Very good (194 reviews)
    "The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
    Reviewed October 17, 2026
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • Nonstop
    $1,565
    $769
    per traveler
    found 12 hours ago
    Boston Lodge and Suites
  • A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
    Jan 25 - Jan 29

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • 1 stop
    $1,994
    $1,147
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • A hotel with a well-maintained garden, a central fire feature, and a sign reading "Sea Crest".
    Jan 15 - Jan 18

    Sea Crest Beach Resort + Flight

    North Falmouth
    3 nights
    3.5 star property
    7.6/10 - Good (550 reviews)
    Roundtrip • Miami (MIA) - Boston (BOS)
    MIA - BOS • Nonstop BOS - MIA • Nonstop
    $710
    $503
    per traveler
    found 23 hours ago
    Sea Crest Beach Resort
  • An indoor swimming pool with a wooden ceiling and tiled floor.
    Jan 15 - Jan 18

    Brewster Green Resort + Flight

    Brewster
    3 nights
    3.5 star property
    9.4/10 - Exceptional (153 reviews)
    Roundtrip • Miami (MIA) - Boston (BOS)
    MIA - BOS • Nonstop BOS - MIA • Nonstop
    $757
    $540
    per traveler
    found 23 hours ago
    Brewster Green Resort

Where to stay in Pinehurst

Find the best Pinehurst areas and neighborhoods for the activities you enjoy most. Learn more about Pinehurst
Learn more about Pinehurst
Quincy Market with an American flag, historic buildings, and a clock tower in the background.

Downtown Boston

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

Back Bay

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

A city skyline at dusk with illuminated buildings reflecting on the water, a prominent bridge, and a large chain barrier along the waterfront.

Seaport District

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.

Beacon Hill

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

Pinehurst Hotel Deals

A spacious lobby with a reception desk, seating area, and a staircase leading to an upper level.

Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
1.4 mi from Pinehurst
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice place and people"
$105 nightly
The price is $118
Nov 13 - Nov 14
Total with taxes and fees
Hampton Inn Boston Bedford Burlington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Pinehurst
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.