First, a disclaimer, I own a condo at the Talamore Golf Resort, so that's where most of my knowledge comes from. I can highly recommend staying at Talamore, but all the condos are set up with 2 double beds in each bedroom. You'll pay a little more for each guy to have his own room, but thats your choice. The folks at Talamore can book golf for you at almost all the local courses, with a notable exception being Pinehurst #2. As Jim mentions, a lot of the hotels will also book golf packages.
If you want to play #2, I'd recommend you stay at the Pinehurst. Resort. As Jim mentions, Pinehurst runs 3 hotels: the Carolinian, which is the largest of the group, the Holly, their original hotel in the Village, and the Manor Inn, which seems to be a more budget-friendly choice. I stayed at the Holly Inn quite a few years ago, and its lovely. The Pinecrest is also right in the village, was once owned by Donald Ross, and its a great place to stop for a drink, even if you don't stay there.
Jim also mentions two of my favorite places, Pine Needles and Mid Pines. both offer full-service resort accommodations, and two excellent golf courses. MidPines has the best veranda to watch golf from, a great look down at their 18th green. If it interests you, both also will let you walk, instead of insisting you ride a cart. The only drawback to staying at either one is that you need to drive to get to either Southern Pines or Pinehurst if you want to eat someplace other than the in-house restaurant.
Spring and fall are indeed the best times to go to Pinehurst, also the most crowded, and the most expensive times. We usually go in February or March, and again at Thanksgiving. the weather is sometimes a little brisk, but we don't pay a lot to stay, so we haven't lost much if we decide not to play golf.
If you decide to visit Pinehurst, please post again. I can give a little advice about bars and restaurants as well, we've definitely developed a few favorites.