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.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,335, price is now CA $950 per person
CA $950
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $1,455, price is now CA $980 per person
CA $980
per person
Sep 18 - Sep 20
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (6 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week. We did not have a rental car but the parking garage was easily accessible and secure. We were able to get ubers very easily from the location. The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient. The support staff replied to all our messages in the chat option quickly and were very helpful. The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred. Would recommend this place without hesitation.

Reviewed on Jun 15, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,832, price is now CA $1,935 per person
CA $1,935
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,004, price is now CA $2,054 per person
CA $2,054
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Neat, clean, and friendly staffing.

Reviewed on Jul 28, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,343, price is now CA $1,649 per person
CA $1,649
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)

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 $337 per night from Aug 6 to Aug 7
CA $337
CA $450 total
Aug 6 - Aug 7
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 $201 per night from Aug 16 to Aug 17
CA $201
CA $234 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (2,778 reviews)
"I travel to Boston frequently, and I stay at The Revilution almost every time. Its generally clean, check in and check outs are quick and easy, parking garage is down the street if you need one, and in a convenient area."

Reviewed on Jul 29, 2026

The Revolution Hotel
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Aug 30 to Aug 31
CA $206
CA $289 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (7,405 reviews)
"The staff was extremely helpful during our stay and it was a great location in the middle of downtown Boston. We would stay here again."

Reviewed on Jul 29, 2026

The Dagny Boston
See all 3,830 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 $950. 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 $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 $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 $68
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.