Pittsboro Vacations from $572

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Your Pittsboro Vacation

The lively city of Pittsboro is calling. Immerse yourself in everything it has to offer with a Pittsboro vacation package that's tailored to you. Carolina Tiger Rescue, The Joyful Jewel and Starrlight Mead are just some of the many attractions worth checking out during your trip to Pittsboro. A few quick clicks is all it takes to build a tailored Pittsboro vacation on Expedia.

The Latest Pittsboro vacation packages

Price found within the past 48 hours. Click for updated prices.
Unscripted Durham, Part of JDV by Hyatt

Unscripted Durham, Part of JDV by Hyatt

3.5 out of 5
Downtown Durham
Save 100% on your flight
Price was $830, price is now $572 per person
$572
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.2/10 Very Good! (1,002 reviews)
Windowless room. Weird.

Reviewed on Jan 18, 2026

Homewood Suites by Hilton Raleigh/Cary

Homewood Suites by Hilton Raleigh/Cary

3 out of 5
Save 100% on your flight
Price was $864, price is now $606 per person
$606
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.6/10 Excellent! (934 reviews)
Breakfast was great! Something I look forward to. Room was clean but it is beginning to show a little age. And this is why they are in the middle of a full renovation! I look forward to visiting again when everything is fresh.

Reviewed on Dec 28, 2025

Sheraton Imperial Hotel Raleigh-Durham Airport/RTP

Sheraton Imperial Hotel Raleigh-Durham Airport/RTP

3.5 out of 5
Save 100% on your flight
Price was $983, price is now $693 per person
$693
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.6/10 Excellent! (853 reviews)
The hotel and room was clean. Close to the airport. No issues there, but we had to pay for parking. $10 per day, even as a guest. That was unexpected and not justified. Other than that it’s a pretty decent place to stay for a couple nights.

Reviewed on Jan 19, 2026

Wingate by Wyndham Raleigh South / Garner

Wingate by Wyndham Raleigh South / Garner

2.5 out of 5
Save 100% on your flight
Price was $829, price is now $590 per person
$590
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.6/10 Excellent! (1,004 reviews)
Room was clean, staff was friendly and breakfast was okay

Reviewed on Jan 20, 2026

The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Downtown Raleigh
Save 100% on your flight
Price was $1,227, price is now $893 per person
$893
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.6/10 Exceptional! (1,001 reviews)
The Longleaf was way better than expected! Super clean rooms, the friendliest staff, and the bar downstairs was so cute.

Reviewed on Jan 20, 2026

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Discover the most popular places to visit in Pittsboro

Vista Point Beach

Why not spend a lazy afternoon at Vista Point Beach during your trip to Pittsboro? Take in the art scene while you're in the area.

Vista Point Beach

Starrlight Mead

You can enjoy a tasting or tour at Starrlight Mead during your travels to Pittsboro. Make time to visit the cathedral and shops while you're in the area.

Starrlight Mead

McIntyre's Fine Books and Bookends

Enjoy a stop at McIntyre's Fine Books and Bookends, an entertaining place to visit in Fearrington. Attend a sporting event or simply visit the area's stunning cathedral.

McIntyre's Fine Books and Bookends

Pittsboro Hotel Deals

The Umstead Hotel and Spa

The Umstead Hotel and Spa

5 out of 5
100 Woodland Pond Dr Cary NC
$393 nightly
The price is $446 total per night from Feb 8 to Feb 9
$446 total
Feb 8 - Feb 9
Total with taxes and fees
9.4/10 Exceptional! (722 reviews)
Great property: However, both the restaurant and guest attire was not congruent with a what a 5- start restaurant should be. Portions were nonexistent and after spending $360 for dinner I left the table starving; not to mention, allowing jeans and t-shirts for "fine dining" is embarrassing. Needless ...

Reviewed on Jan 11, 2026

The Umstead Hotel and Spa
Sonesta Select Raleigh Durham Airport Morrisville

Sonesta Select Raleigh Durham Airport Morrisville

3 out of 5
2001 Hospitality Ct Morrisville NC
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Jan 29 to Jan 30
$114 total
Jan 29 - Jan 30
Total with taxes and fees
8.6/10 Excellent! (1,726 reviews)
Clean rooms and kind staff

Reviewed on Jan 14, 2026

Sonesta Select Raleigh Durham Airport Morrisville
Country Inn & Suites by Radisson, Raleigh-Durham Airport, NC

Country Inn & Suites by Radisson, Raleigh-Durham Airport, NC

3 out of 5
201 Airgate Dr Morrisville NC
Fully refundable
$93 nightly
The price is $105 total per night from Jan 29 to Jan 30
$105 total
Jan 29 - Jan 30
Total with taxes and fees
8.2/10 Very Good! (1,881 reviews)
Room spotless and staff was amazing as always

Reviewed on Jan 15, 2026

Country Inn & Suites by Radisson, Raleigh-Durham Airport, NC
See all 1,806 properties in Pittsboro
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.

Find the Best Pittsboro Vacation Packages

Pittsboro Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Raleigh - Durham Intl. Airport (RDU)
Population
4,200
Max Temp Winter
50ºF
Max Temp Summer
90ºF
Top Sights
Carolina Tiger Rescue, Starrlight Mead and SilkHope Winery

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Frequently asked questions

How much does a Pittsboro vacation package cost?
You can pick up a vacation package to this destination from $572 on Expedia. But how much your vacation to Pittsboro costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Pittsboro?
May, September and December are great times to look for cheap Pittsboro vacation packages. Choosing to travel in quieter months means you can usually find reduced prices on flights and hotels.
How many days is enough for Pittsboro?
With a well-organized itinerary, you can easily visit the main Pittsboro attractions in a handful of days. But if you'd like to venture off the beaten track or take day trips, consider booking your Pittsboro vacation for longer.
How to find the best Pittsboro package deals?
Start your search for a Pittsboro package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Pittsboro package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Pittsboro escape off to a flying start.
Is it cheaper to book a Pittsboro vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and accommodations individually. Better still, you can tailor your Pittsboro getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Pittsboro?
If you've got your Pittsboro travel dates finalized, book as early as you can to bag some outstanding deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Pittsboro?

  1. Choose your travel dates: The things you'd like to do in Pittsboro and your favorite season will help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to flights and activities. Your accommodations will likely be the biggest expense during your trip to Pittsboro.
  3. Explore Pittsboro using Expedia's trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Pittsboro. You can also save your favorite locations, collaborate with family and friends and organize your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Pittsboro, you can figure out the ideal length of your break. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  5. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the ideal Pittsboro vacation package for you.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some fun things to do in Pittsboro. Book tickets or make reservations as soon as you can to save time and avoid the stress of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Pittsboro vacation packages?
Set off on your dream trip to Pittsboro with help from our Book Now, Pay Later vacations. There's no need to save up or wait until payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snag great deals before they disappear.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.