1. Summersweet Bed & Breakfast

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    Chilmark, MA

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    Summersweet Bed & Breakfast

    5.0 (2 reviews)

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    1720 House

    1720 House

    (21 reviews)

    $$$

    Great location great vibe cozy rooms - brought my sorority sisters & had a great time very intimate…read more& nostalgic .. loved all the books & the beautiful yard Rented a bike and swam at the nearby town beach

    Spent memorial weekend in Martha's Vineyard and 1720 House was our choice of accommodation. This…read moreplace was introduced in NY Times 36hrs and was the only option that wouldn't cost an arm and a leg. They were very nice to bend their 3 day reservation rule and allowed us to stay for two days. We paid ~ $250/night including tax. Location is good, about a 5 minute walk from the dock along main street. However, I did see some B+B's with better locations once I arrived to the island. I guess this is why you have to be 'in the know'. We stayed in the Americana Room with a private bathroom. Bathroom door opens to the hall way and the lock did not work making us a bit nervous every time we had to use the bathroom. The room had one queen size bed and a side bed. The side bed was too lumpy and uncomfortable. Breakfast is included but meh.. it's just cereal or stale bread/bagel and a few pieces of fruit. Coffee and yogurt is also on the table but they are both the weak and flavorless kind. The cleaning staff was very nice but kinda pushy with the tip. Deliberately leaving two envelopes for tip in visible areas. All in all, it was ok because I got to experience a 'traditional american B+B' but I wouldn't go here again unless I'm in a pinch.

    Charles and Charles

    Charles and Charles

    (20 reviews)

    $$$

    We had a wonderful stay at Charles and Charles for our annual mother/daughter weekend. Because…read morethere were three of us we stayed in the loft 2bd/2bath Edgartown room which was spacious yet cozy. We appreciated the thoughtful details around the room like the warm towel racks, the homemade oatmeal and coconut cookies, the bottle of wine that was left in the fridge (which we most certainly drank!). The property itself was well manicured and beautiful, and the homemade breakfast was to die for. We were given great suggestions for things to do as well which we took advantage of on our last day and we're so glad we did. On our last morning we let them know we were leaving early for the airport and they dropped off homemade strawberry scones which were the perfect on the go breakfast for our ferry ride back to Woods Hole. If you're looking to experience a clean and inviting place with 5 star hospitality, Charles and Charles is a must!

    THIS PLACE IS AMAZING!!!! The first B&B I've ever stayed at, this place was incredible. From…read morerelaxing in their swing outside to their amazing breakfast this place is the bee's knees. The owners are actually from LA so we connected about that, and they actually took us to the ferry on our last day as we went to Nantucket. A very special place, we also loved borrowing the bikes and riding all over the island. This place is perfect. The only tip I would have though is to bring earplugs because the beds are so comfortable you will hear snoring from your neighbours :)

    High Haven House

    High Haven House

    (3 reviews)

    $$$

    My wife and I stayed here for our first trip to the Island. We really liked our "little apartment"…read moreset up. We had an upstairs unit that has its own private entrance. There are two rooms, a living room, a kitchen and a clean bathroom that was a bit tiny, but very serviceable. Everything was clean and tidy upon our arrival. The service was fine. We never tried the breakfast, so I can't help you there. The location was 10 to 12 minutes of walking from Main St, which for us made it very convenient. We would stay here again. And we may on our next trip to the Island.

    We received a bed and breakfast gift card for our weddng and decided to stay at this highly rated…read morebed and breakfast in Vineyard Haven. My wife and I were so glad it was free because if we paid, it would have been robbery. The location is not bad, sittng on top of the hill from the downtown area of Vineyard Haven and what ever you do, dont take a cab from the ferry. We took one and we could have walked and it was a rip off and they got lost to boot. The place is a regular under construction suburban house with a pool but something out of the 1970's with shabby interiors and just an all around mess of an inside. The inn keeper tries to hide the shabby quality but the furnishings are dated and old and falling apart. The set up is a disarray of rooms and apartments that are furnished with cheap furnitiure and rugs and uncomfrotable beds. The rooms were filthy and the bathrooms were nasty. The steet it sits on is quiet and but is tucked a ways back. The breakfast served was trying to be good but was lacking quality. the place really should close down and not boast being a 5 star bed and breakfast because it is far from it. There are so many places to stay on this island, if you are going to spend the money, you can do a lot better than this spot. It is a downright rip off for the quality. Skip it.

    Summersweet Bed & Breakfast - hotels - Updated July 2026

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