Concierge.com's insider take:

In May 2008, a stem-to-stern renovation of this gray-shingled Victorian was completed under the watchful eye of owner Alan Worden (a former investment banker who once sailed from Nantucket to New Zealand with just one other crew member). Originally opened on the Edgartown Harbor in 1891, this grand New-England–style resort is the town's oldest and—with 141 rooms spread among two main buildings and several cottages—largest hotel. Linda Woodrum, of HGTV's Dream Homes, redecorated the cottage suites, and while they feel plucked out of a Pottery Barn catalog, they have the best of everything: kitchenettes, walk-in closets, flat-screen TVs, fireplaces, private gardens, and outdoor showers. Ask for suite 24 in the cottages for its relative seclusion, ocean view, and brand-new, high-end appointments; or for any of the more traditionally decorated, ocean-facing rooms in the main house (some of which have private balconies). Avoid the motel-like Governor Mayhew building by the pool. The restaurant, Water Street, turns out sophisticated New England–style dishes, and the comfortable bar, Henry's, serves an all-day menu of crowd-pleasers, such as lobster rolls and chocolate-chip cookies. Befitting the hotel's maritime feel, a 31-foot center console boat ferries guests to private beaches (although there is a small sand beach and heated pool on site), and the young-adult learn-to-sail program will keep the kids occupied while you watch from the wraparound porch as yachts drift by. The town is a five-minute scenic walk away—far enough to keep the hotel's vibe relaxed. Guests also get advance tee times at the nearby par-72 Farm Neck Golf Club, and a spa and health club are planned.

Note: The Harbor View has announced plans to sell off up to half of its units as condos (priced from $526,000 to $1.3 million). The rest will remain available to guests.

Open mid-May through late October.