Pinehurst Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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 $1,931, price is now CA $816 per person
CA $816
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
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 apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $1,647, price is now CA $1,034 per person
CA $1,034
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,031, price is now CA $1,374 per person
CA $1,374
per person
Dec 29 - Jan 2
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $1,982, price is now CA $1,354 per person
CA $1,354
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,354 reviews)

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Lexington Green Historic District
Save 100% on your flight
Price was CA $1,638, price is now CA $1,125 per person
CA $1,125
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (268 reviews)
Gorgeous and cosy with great breakfast

Reviewed on Oct 22, 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

Pinehurst Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Nov 22 to Nov 23
CA $219
CA $312 total
Nov 22 - Nov 23
includes taxes & fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Nov 23 to Nov 24
CA $148
CA $172 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (2,995 reviews)
"Everything is great but price."

Reviewed on Oct 29, 2026

The Revolution Hotel
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 $202 per night from Nov 29 to Nov 30
CA $202
CA $283 total
Nov 29 - Nov 30
includes taxes & fees
Seaport Hotel Boston
See all 3,770 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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Pinehurst vacation package cost?
Explore the best of Pinehurst from as low as CA $816. 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 $69
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 $119
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 $65
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.