Pinehurst Vacation Packages

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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.

Top Holiday Package Deals in Pinehurst

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

Downtown Boston
CA $1,021
per person
Nov 26 - Nov 29
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,007 reviews)
Beautiful hotel in a great location. The staff were lovely. My stepson loved the paddington bear bowl of cookies and sprinkles. Nice touch.

Reviewed on Sep 13, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
CA $1,229
per person
Nov 26 - Nov 29
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
What a great hotel

Reviewed on Sep 13, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
CA $1,689
per person
Nov 6 - Nov 9
found 14 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (484 reviews)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

Back Bay
CA $1,720
per person
Nov 6 - Nov 9
found 14 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (451 reviews)
Meco Hotel - Hostel

Meco Hotel - Hostel

West End
CA $1,092
per person
Oct 23 - Oct 26
found 6 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (531 reviews)
This place is perfect for solo travels

Reviewed on Sep 13, 2026

Where to stay in Pinehurst

Find the best Pinehurst areas and neighborhoods for the activities you enjoy most. Learn more about Pinehurst
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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.

Find hotels in Downtown Boston
A historic building with ornate architecture, a staircase, and a tree in front.

Back Bay

1 out of top 10 points of interest in this area

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.

Find hotels in Back Bay
A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.

Seaport District

1 out of top 10 points of interest in this area

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.

Find hotels in Seaport District
A street lamp with a lit bulb, surrounded by trees and a brick building.

Beacon Hill

1 out of top 10 points of interest in this area

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.

Find hotels in Beacon Hill
A bustling riverside area with a prominent building featuring a large arched entrance, a dock with a boat, and a crowd of people.

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.

Find hotels in North End

Pinehurst Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $357
CA $473 total
Sep 20 - Sep 21
includes taxes & fees
9.2/10 Wonderful! (4,820 reviews)
"Good location, easy parking with valet out front, clean rooms, nice bathrooms"

Reviewed on Sep 13, 2026

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $373
CA $482 total
Sep 20 - Sep 21
includes taxes & fees
9.6/10 Exceptional! (4,987 reviews)
"Fantastic hotel Lovely and clean Very polite and helpful staff In a great area"

Reviewed on Sep 14, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
CA $299
CA $348 total
Sep 20 - Sep 21
includes taxes & fees
9/10 Wonderful! (2,930 reviews)
"Great experience"

Reviewed on Sep 14, 2026

The Revolution Hotel
See all 3,799 properties in Pinehurst
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.
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Frequently asked questions

How much does a Pinehurst vacation package cost?
Explore the best of Pinehurst from as low as CA $1,021. Choose from a wonderful selection of flights, hotels and rental cars to suit your travel style. Pick up even more discounts when you add a few sightseeing activities to your vacation package.
How do I get a cheap travel package to Pinehurst?
You'll save big if you bundle your hotels, flights and car rentals into a Pinehurst travel package. Sometimes cheap means fewer choices. But not with Expedia. We offer over 550 air carriers and 1,000,000 hotels all over the world, so you'll always have plenty of options to choose from. Like to save even more? Add some popular activities to your package deal to unlock even more discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Pinehurst?
Stay close to the action. Many people favor hotels within easy reach of top sights, such as Clara Sexton House, Country Club of Billerica and Nutting Lake Conservation Land.
How far in advance should I book my Pinehurst vacation?
Travelers can normally browse international airfares on Expedia up to 12 months prior to departure. Booking late? With a little bit of luck, it's still possible to purchase a cheaper ticket only weeks before your journey.
What does an Expedia Pinehurst travel package include?
Expedia has all you need to book your Pinehurst escape, but what goes into your package is entirely up to you. Select from a combination of hotels, rental cars and flights. In search of some tours or activities to keep you on the move? Once you've made your booking, you can add them on too. No matter your budget or style, there's a package to match your needs.
What should I know before booking a Pinehurst travel package?
You'll land terrific savings when you bundle your hotels, flights and rental cars into a travel package. Not just that, booking everything together makes trip planning much easier. So why waste your money or time? Whether you're organizing a ritzy city getaway or a budget solo adventure, explore our vacation packages today.
Can I choose my airline with a Pinehurst Expedia vacation package?
With a vacation package, you're in charge. Whether you'd prefer to fly to Pinehurst in coach or first class, simply select from the available airline options. Expedia has access to over 550 airline partners across the world.
If I'm not able to travel, can I cancel my Pinehurst vacation package?
We get it — life can throw you the odd curveball. If you've locked in a Pinehurst vacation package and have to cancel or amend it, we're here to help. We suggest browsing our Customer Service Portal first for information. But in general, if you've taken out your package in the last 24 hours, you may be able to cancel or amend your itinerary free of charge. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a fee.

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $68
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $116
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $64
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.