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Over the past 7 years I’ve had the pleasure of regularly visiting Martha’s Vineyard. I’m fortunate enough to be able to call a family vacation cottage home base while on the island, but having had my wedding in Edgartown I became an expert on the best hotels in the village in order to ensure our guests had an idyllic experience. Here are my top 5 picks for where to stay in style:

Harbor View Hotel
Built in 1891, last renovated in 2013, this luxury Edgartown escape overlooks the famous Edgartown Lighthouse, harbor and Chappaquiddick Island. Amenity highlights include an outdoor heated pool (not very common in Edgartown), complimentary children’s activity program, private parking (also uncommon in Edgartown), and multiple dining venues on site. June and Sept.: from $239 a night July-Aug.: from $439 a night.
Harbor View Hotel

Vineyard Square Hotel & Suites
Located in a prime spot in the heart of the historic downtown where all of the best restaurants and shops are located, guests receive continental breakfast daily, complimentary bikes to use (the preferred mode of transportation around town), on-site salon and day spa as well as a beautiful front porch complete with more than a dozen rocking chairs to take partake in some great people watching. June and Sept.: from $155 a night July-Aug.: from $225 a night.
Vineyard Square Hotel & Suites

Hob Knob
This eco-chic luxury boutique hotel, which has played host to JFK, is just a few minutes walk from the heart of Edgartown. Picnic lunches, beach chairs and umbrellas are available via the guest concierge as well as local farm to table breakfast and afternoon tea. A highlight is the 27’ Boston Whaler with captain available to reserve for fishing trips, sunset cruises or some island touring from the water. June and Sept.: from $399 a night July-Aug.: from $449 a night.
Hob Knob

Winnetu Oceanside Resort
Named in 2015 as one of the “Top 100 Hotels in the World” by Condé Nast Traveler, Winnetu is the only hotel located just above the shoreline of popular South Beach. 1-4 bedroom suites, private cottages as well as private rental homes ranging from 2-5 bedrooms are available to book. Having one of the most popular beaches on the island at your doorstep is a serious perk, plus the hotel offers a complimentary shuttle to and from downtown, tennis club, yoga, multiple pools and children’s programs. June and Sept.: from $195 July-Aug.: from $515.
Winnetu Oceanside Resorts

The Charlotte Inn
Entering its fifth decade in business, this inn offers the attention to detail, service and quality that Relais & Chateau properties such as this one have come to be known for. Edwardian in décor with all of the modern amenities, the inn bestows an elegance of a bygone era. Flanked by historic whaling captain homes, the setting is quintessential Edgartown. There is also the bonus of Hermès and Bulgari toiletries. June and Sept.: from $395 July-Aug.: from $450.
The Charlotte Inn

Hillary Leo writes for us and also her own travel blog SwoonFor.

Disclosure: Our property, service and product reviews are sponsored by the proprietor or brand being appraised. All opinions remain our own and are in no way influenced by the sponsor.

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