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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,004, price is now CA $517 per person
CA $517
per person
Oct 28 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,679, price is now CA $1,464 per person
CA $1,464
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
Lovely property and staff. Great location and spa. Will return!

Reviewed on Aug. 26, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,003, price is now CA $1,158 per person
CA $1,158
per person
Oct 18 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug. 24, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,625, price is now CA $956 per person
CA $956
per person
Oct 31 - Nov 2
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (482 reviews)
Love the Street Bar!

Reviewed on Aug. 25, 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
Price was CA $1,450, price is now CA $974 per person
CA $974
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,326 reviews)
Nos encanta este hotel y siempre volvemos.

Reviewed on Aug. 24, 2025

Where to stay in Pinehurst

Find the best Pinehurst areas and neighborhoods for the activities you enjoy most. Learn more about Pinehurst
Downtown Boston showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(193 area reviews)

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

Pinehurst Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Sep 1 to Sep 2
CA $212
CA $253 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,276 reviews)
"Clean comfortable room with massive comfy bed. Very conveniently situated for the cruise port. Staff were extremely professional, friendly and helpful."

Reviewed on Aug. 25, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $282 per night from Sep 1 to Sep 2
CA $282
CA $385 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,870 reviews)
"We stayed for a couple of days at the end of our trip to Boston, the hotel was perfect for relaxing by the pool and a short walk from all the areas we wanted to see whilst visiting."

Reviewed on Aug. 25, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Sep 1 to Sep 2
CA $255
CA $296 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,692 reviews)
"Decor and furnishings unique. Refreshing and different. View from lounge area of Boston skyline is amazing!"

Reviewed on Aug. 24, 2025

citizenM Boston North Station
See all 3,534 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

Frequently asked questions

How much does a Pinehurst vacation package cost?
Explore the best of Pinehurst from as low as CA $517. 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.

Discover the most popular places to visit in Pinehurst

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.