The Cottages & Lofts at the Boat Basin, Nantucket, Massachusetts

The 24 cottages offer the best of both worlds: They hang over the harbor water but are steps away from downtown. The renovated cottages have kitchens, and the front desk will stock them with your shopping list prior to your arrival. That’s what we call rock star room service!

Field trip: Arrange a private sail aboard Endeavor at the dock outside the cottages and enjoy a sunset cruise for two or a pirate-themed adventure with the kids.

Night out: You might hear a live piano and sing-along on a stroll through downtown. That’s The Club Car, an iconic seafood and steak restaurant in an old train car.

Rates: from $175 (spring/fall) to $1,100 (summer); 866/838-9253 or thecottagesnantucket.com