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 Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Price was CA $714, price is now CA $549 per person
CA $549
per person
Mar 14 - Mar 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (802 reviews)
Everyone was nice, the room was decent size and there were options. Water was HOT! I loved it

Reviewed on Feb 3, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,201, price is now CA $1,490 per person
CA $1,490
per person
Apr 3 - Apr 6
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $2,104, price is now CA $1,566 per person
CA $1,566
per person
Mar 12 - Mar 16
found 19 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,163, price is now CA $2,384 per person
CA $2,384
per person
Apr 23 - Apr 26
found 23 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Everything was great — room was immaculate, hotel was very nice. Would return!

Reviewed on Feb 1, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,572, price is now CA $1,194 per person
CA $1,194
per person
Apr 3 - Apr 6
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

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

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $147 per night from Feb 8 to Feb 9
CA $147
CA $171 total
Feb 8 - Feb 9
includes taxes & fees
9.2/10 Wonderful! (6,199 reviews)
Best price for the location! Always clean and great staff!

Reviewed on Feb 4, 2026

Harborside Inn Of Boston
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 $88 per night from Feb 9 to Feb 10
CA $88
CA $103 total
Feb 9 - Feb 10
includes taxes & fees
9/10 Wonderful! (2,439 reviews)
Excellent customer service, beautiful room!!

Reviewed on Jan 31, 2026

The Revolution Hotel
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $513 per night from Feb 28 to Mar 1
CA $513
CA $597 total
Feb 28 - Mar 1
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

The Langham, Boston
See all 3,909 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
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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 $549. 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
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium
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 Hop-On Hop-Off Trolley Tour

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

CA $73
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 $110
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit.

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% 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.