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Hotels in Massachusetts
196 Hotels
Winstead Inn
116 Parallel St

Oak Bluffs Inn
64 Circuit Ave.

The three-pearl Oak Bluffs Inn is a lovely bed-and-breakfast perched at the top of Circuit Avenue in the heart of Oak Bluff’s restaurants and shops. It’s only a five-minute walk to the beach and eight minutes on foot to the ferry departure at the marina. Guests receive a free breakfast, fresh baked cookies in the afternoon, and free snacks and drinks from the pantry 24/7. It’s a casual and friendly place with a wrap-around porch that’s great for people-watching. Its 10 rooms are clean and individually decorated with private bathrooms. But, some rooms are small with cramped bathrooms, and none have TVs. It’s fairly priced with free Wi-Fi and off-street parking, but the nearby, mid-range Pequot Hotel offers lower rates on most dates as well as free breakfast and TVs in most rooms.

Pequot Hotel
19 Pequot Ave

The mid-range, boutique Pequot Hotel offers excellent rates for a Martha's Vineyard property just one block from the beach. Its 32 rooms are clean and decorated in a beach-cottage style, but they vary significantly in size, layout, and amenities. Standard rooms can be quite small with cramped bathrooms, and some rooms have no TVs. Others include mini-fridges or even a furnished deck. The hotel's features emphasize its friendly and comfortable vibe, with a free breakfast, afternoon snacks, and a weekly wine-and-cheese reception with music. Free parking and free Wi-Fi enhance its value. Overall, it’s a good choice, which means it's frequently sold out. A good backup is the three-pearl Oak Bluffs Inn, but expect higher rates at this lovely 10-room bed-and-breakfast.

Holiday Inn Boston Bunker Hill Area
30 Washington St

The Holiday Inn Boston-Bunker Hill is a pleasant mid-range hotel that appeals to a wide variety of travelers. The hotel's location on an industrial block subjects guests to gritty views of aging buildings, transfer trucks, and a mechanic shop. However, the free shuttle and location a 10-minute drive to both Cambridge and the airport is reasonably convenient (for those who don't need to be in Boston proper). Amenities include a recreation area featuring a rock climbing wall, indoor swimming pool, and basketball court. The 184 contemporary rooms include a coffeemaker, flat-screen TV, and mini-fridge. Decor is nicer than expected for a chain hotel, especially in the lobby set with local art. Draft restaurant serves a selection of craft beer and a dinner menu, but the breakfast buffet costs extra. The nearby La Quinta Inn & Suites Boston Somerville has cheaper rates, but fewer amenities. 

Mansion House
9 Main St.

The mid-range Mansion House Inn is a cute 48-room bed-and-breakfast-style hotel with charming country-beach decor. One draw is the attached Health Club, free for hotel guests but used by locals, too. There are separate cardio and weight rooms, a huge range of workout classes, plus an indoor lap pool, whirlpool, sauna, steam room, and spa treatment rooms. A basic cold continental breakfast is served daily, free of charge, and an Asian-fusion restaurant is also attached to the property. The central Main Street location means a quick walk to restaurants, cafes, shops, the beach, the ferry, and the local bus, though some find Vineyard Haven a little too low-key. Guests looking for a more intimate inn-experience in a slightly more happening area might consider the Oak Bluffs Inn, though it lacks the extensive wellness amenities of Mansion House.

The Hob Knob
128 Main Street, Upper Main Street & Tilton Way

Located centrally along a quaint stretch of Main Street, the Hob Knob is a welcoming bed & breakfast with a well-landscaped yard and wrap-around porch. Of course, in high-tourist season the prices reflect its status as a popular boutique -- but in a lot of ways, you do get what you pay for. Rooms are spacious and comfortable with Berber carpeting, luxurious European linens and bathrobes, lovely Classic American-cottage decor (though some rooms feel more tended to than others), and pretty bathrooms with marble sinks. Other highlights include the free organic, full-farm breakfast, and the fact that downtown Edgartown is a short walk away. This place isn't really geared toward families, though -- children under the age of seven aren't allowed, and teens would likely be bored by the lack of a pool on-site.