Pinehurst

Pinehurst is the purest golf trip in America. Ten courses inside the resort with an eleventh opening in 2027, more in the village, caddies who have looped for forty years, and No. 2 sitting there as the thing you tell people about. Stay and play packages bundle rooms, meals and rounds into one number per head, which makes it the easiest trip on this site to collect money for. Everyone pays once and it is done.

It is wrong for anyone who does not golf. There is no nightlife, the village shuts down early, and a non-golfer will spend three days in a rocking chair. It is also wrong for a group looking for a party. The bar is a bar in a golf resort, and the loudest thing that happens is a putting contest on Thistle Dhu.

Everyone searches for a Pinehurst stay and play. The resort does not sell one under that name. The product is the Bed, Breakfast and Golf package: your room, one round per night, breakfast daily, cart included. Dinner is not in it.

The Holly Inn, The Manor and the two bedroom condos are priced identically. Same package, same rate, so pick on the room and not the number. The Carolina Hotel runs roughly $130 to $190 more per man per night. The Carolina Villas run another $180 to $210 above that.

Season moves the number more than the building does. A double at The Manor is $730 per man per night in October and $310 from late November through February. Same package. That is a 58 percent cut for playing in a fleece.

No. 2 carries a $250 premium on top and No. 10 carries $125, and you need a two night minimum to play No. 2, No. 4 or No. 10 at all. Most weekends from mid March to mid November are three night minimums anyway.

Two variants are worth knowing. Hidden Gems runs 15 percent under the standard package and gets you onto 6, 7, 8 and 9, but 2, 4 and 10 are off the table entirely. The Donald Ross package adds a third night and a fourth round for $199, which is the best value line the resort publishes.

If there are eight to sixteen of you, look at the Cottages at No. 8 instead. They price per cottage rather than per man, so the per head number drops every time you fill another bed. Rates checked September 2026.

Pinehurst reserves advance tee times on 2, 4, 6, 7, 8, 9 and 10 for members and resort guests. There is no day pass and no partner hotel arrangement. If your group wants No. 2, someone is booking resort lodging, and that is the whole reason the package math above matters.

If you are happy with No. 1, No. 3, No. 5 and The Cradle, stay wherever you like and book by phone the day before. Pine Needles and Mid Pines in Southern Pines are both real Donald Ross courses running their own packages, and neither publishes rates online, so you are calling either way.

Fly into RDU and rent two SUVs for the 75 minute drive southwest. Fayetteville is closer but flights are worse and more expensive. Inside the resort everything runs on a free shuttle, so the cars only matter for the trip in and the run to Tobacco Road.

The rate card says $80 for a double bag caddie. That is the fee. The resort then recommends a $60 gratuity per bag, which makes the real number $140 per man per round.

A forecaddie is $40 with a $35 recommended tip, so $75 per man. One forecaddie for a foursome is $300 a round. Four walking caddies is $560. If the group is riding and just wants someone reading greens and finding balls, the forecaddie is the same job for roughly half.

Note that the fee is quoted per player and the tip is quoted per bag. That is how groups end up under-tipping without meaning to.

Caddies are not mandatory anywhere. The resort pushes them on No. 2 and No. 4 because both are cart path only, so a cart saves you almost no walking, and on No. 10 because it is walking only and there is no cart to take. Fees checked September 2026.

Every package rate the resort shows you is before a 10 percent resort fee, a 7 percent sales tax and a 6 percent occupancy tax. Add roughly 23 percent to any number you are quoted, and to the numbers above.

The deposit is $300 per adult at booking. Cancel more than 30 days out and you get it back. Cancel inside 30 days and you lose all of it. For twelve guys that is $3,600 riding on nobody dropping out in the last month, which is exactly when guys drop out. Collect the deposit from your group before you book, not after.