The Ready-Made Golf Trip – Pinehurst 2021

Join us June 17th - June 20th at Pinehurst Resort

The Perfect Itinerary

Pinehurst Resort – Ready-Made Golf Trip by TripCaddie

The Ultimate Bucket List Experience for your Buddies Golf Trip!

Dates: Thu June 17th – Sun June 20th

4 Rounds of Golf (plus The Cradle), 3 Nights at the Holly Inn


Get your group of 4, 8, 12 or more together and register now for this ultimate buddies golf trip experience! Sign up soon to claim your preferred tee times and line up non-golf activities. TripCaddie has taken care of the lodging and golf reservations so you can just pay and show up with your group. This is your trip with your buddies.

Download the flyer for this trip and share it with your group — or send them the link to this page. Everyone will need to acknowledge the Terms and Conditions for the offer including our cancellation policy.

For more information about Pinehurst Resort and Tobacco Road:

Call for Reservations and Payments: (708) 320-8210

Pricing (per person): $2299 for Double room (2 Queen beds, double occupancy) or $2599 for Single room (King, single occupancy)

Accommodations: 3 nights at the Holly Inn, optional extra nights for Wednesday or Sunday night are available (addt’l $309/night single or $155/night double)


Golf includes carts and/or caddies* with rounds at Tobacco Road, Pinehurst #2, Pinehurst #4, Pinehurst #8, and The Cradle


Payments: Each person can pay individually via credit card (call the number above) or Venmo (@tripcaddie). A 50% deposit is required by 4/16 with final balance payments due by 5/16. If paying by Venmo, you will receive a discount of $50 off the package price.


Cancellations: If someone in the group needs to cancel after making a deposit, try to find a replacement to fill the spot to avoid cancellation fees. If you don’t find a replacement, we will have to re-book the room / tee times with another group. If one person in a Double room cancels and you can’t find a replacement, we have to cancel the roommate’s reservation as well. If there’s availability, we can re-book the roommate in a Single room at the higher rate. The full cancellation policy is available in the Terms and Conditions.


Travel recommendations: Raleigh-Durham International is the closest major airport (~1 hour away) but Charlotte Douglas International is also within 2 hours of the resort. You will need to arrange for a car to drive from the airport to the resort. Lock in your tee times before making flight reservations for Thursday and Sunday.


* Additional fees apply for optional activities, individual/double bag caddies, and extra nights lodging. Optional items are subject to availability. Gratuities for all caddies, resort staff and shuttle services are not included but strongly encouraged.

Need Help?

We're Here To Assist You

Prefer to talk to a live person? No problem, feel free to contact us!  Give us a call at 708.320.8210.