Surf Side Cottages, South Wellfleet, Massachusetts $$$$
Concierge.com's insider take:
Located in the Cape Cod National Seashore, this quiet neighborhood with scrub pines and sandy streets is a throwback to family vacations past. The 23 cottages on and near the ocean have full kitchens, barbecue grills, screened porches, and outdoor showers. The decor is '60s retro, the only air conditioning is the ocean breeze, and while there are no TVs, there's a drive-in movie theater in nearby Wellfleet. The residents-only LeCount Hollow Beach is just over the sand dunes; if you rent a cottage here, you're considered a resident. Provincetown is a 20-minute drive away. Since there's no housekeeping service, come with your own linens (or rent them for an additional $15), and remember to clean up for the next guests. There's a one-week minimum in the summer.
Closed November through March.