Hob Knob

Bright hotel dating from 1742, offering classic rooms, an outdoor pool & free refreshments. A 2-minute walk from the waterfront on Martha's Vineyard and 0.2 miles from the tip of Chappaquiddick via ferry, this historic hotel has been open since 1742. The traditional, homey rooms are spread across 4 buildings and feature minifridges, cable TV and free Wi-Fi. Some have kitchens or kitchenettes, and private porches with views of the harbor. Free amenities include morning coffee and tea, evening milk and cookies, and guest parking. There's a seasonal outdoor pool and a poolside bar, and biking and jogging trails are accessible from the property.

Nestled in historic Edgartown, this charming inn from 1798 offers cozy rooms and a vibrant garden, just a stroll from the Yacht Club and local attractions.

Nestled on the harbor in Edgartown, this charming retreat combines vintage appeal with unpretentious comforts, like a heated pool and easy access to local hotspots.

A French-inspired, locally sourced menu served in a classy dining room & wine/cocktail bar.

A menu featuring seafood towers & contemporary bistro fare in a renovated home with patio seating.

Nestled in Edgartown, The Sydney offers a cozy boutique experience with stylishly appointed rooms, delightful breakfast baskets, and a welcoming vibe that makes you feel right at home.

Casual nook in a renovated house serving area-sourced comfort food, local beers & homemade desserts.

Spiffy indoor-outdoor venue for steak & seafood boasts a yacht-club vibe with Nantucket Sound views.

The Christopher is a chic boutique hotel in Edgartown offering bright, stylish rooms, warm hospitality, and a lovely courtyard fire pit just steps from local shops.

Seasonal New American fare & a big wine list star at this chic, romantic venue with outdoor dining.