The rooms at The Nashua House (30 Kennebec Ave., Oak Bluffs, 508/693-0043, www.nashuahouse.com , $69–219) are a bit musty, but you can’t beat the view of the ocean from rooms with pastel walls and battered antiques.
A laid-back and centrally located bed-and-breakfast, the Look Inn (13 Look St., Vineyard Haven, 508/693-6893, $125) has a hot tub in the backyard and friendly innkeepers who give free personalized tours of the island.
A pink wedding cake of a house at the top of Oak Bluffs ’ main drag, the Oak Bluffs Inn (64 Circuit Ave., Oak Bluffs, 800/955-6235, www.oakbluffsinn.com , Apr.–Oct., $140–300) is appointed with a tasteful mix of modern country furniture and old English antiques. It has an informal, lived-in air that makes staying there feel like bunking at Grandma’s.
Up-island, the secluded Duck Inn (10 Duck Pond Way, Aquinnah, 508/645-9018, www.gayheadrealty.com , $135–195) is located in an 18th-century home with bohemian furnishings and a knockout ocean view. One room has a bathtub in the middle; another is swept at night with the beam from Gay Head Light. The personable owner is a 30-year island resident who gives therapeutic massages and makes killer organic breakfasts.
Located by the beach outside of Edgartown , the
Winnetu Inn & Resort (31 Dunes Rd., Edgartown, 508/627-4747, www.winnetu.com , $195–890) offers luxury without pretension. The managers pride themselves on being both kid-friendly (witness the giant-sized chessboard in the courtyard) and relaxing (a strictly enforced “quiet time” begins at 9 p.m.). All-suite kitchenettes are beach-house minimalist, many with views of the surf. Activities include oceanside tennis courts and yoga.
Your fantasies of living as a sea captain can be fulfilled at the over-the-top romantic Charlotte Inn (27 S. Summer St., Edgartown, 508/627-4151, charlotte [at] relaischateaux [dot] com, www.relaischateaux.com , $325–795), where a personal touch is evident in every detail of plush, individually decorated rooms. The innkeepers use a collection of hand-chosen antiques to make you feel at home, for example putting an old top hat on your bed or antique looking-glass on your desk when you return at night. Behind the house, gardens are filled with a fantasia of flowers and sitting areas, and the dining room has glass walls.
On the other side of the island, the Beach Plum Inn (50 Beach Plum Ln., Menemsha, 508/645-9454, info [at] innatmenemsha [dot] com, www.beachpluminn.com , $225–450) is a secluded retreat, with six acres of hilltop property overlooking Vineyard Sound and the Elizabeth Islands. Rates include a full breakfast and a coveted pass to the residents-only Lucy Vincent Beach, one of the most beautiful on the island.