Bed and breakfast vacation rentals in Oak Bluffs

Marjory is the kindest, most thoughtful host. And the studio is perfect. Quiet, and surrounded by the most peaceful West Tisbury meadows. It’s the ideal launching place for up island explorations, days at Lamberts Cove, and just generally relaxing and getting into that deep calm of rural Vineyard vibes. I’ll be back!

amazing host and location. Very communicative when we had a small hiccup due to the time I had to be at a wedding. They took care of the situation quickly

We stayed a few nights and the inn was quaint and cozy. Perfectly located to restaurants and shops. Our host Jeanette was friendly and very helpful. The continental breakfast was served in the cutest dining area and her homade coffee cake was delicious.

Paul’s place is like a museum! So much history and he takes great pride in it! Tracey met us and gave us all the important info we needed! We got settled in and felt right at home. The bed was so comfortable and the newly refinished bathroom was large with a shower that had great pressure. The breakfast the next morning, wow! It was perfection! Thank you Tracey and Paul! We will definitely be back!

Words fall short in describing this beautiful property. A short drive from the Vineyard Haven ferry terminal, staying at Charles and Charles is an amazing oasis within an already gorgeous island. The location is great - close enough to drive to anywhere you want to be within a short time, and far enough to feel like you are at a garden retreat, Charles and Debby make you feel welcomed and taken care of. From a bottle of wine and cookies waiting for us at check in, to daily room cleaning, to the best homemade breakfast you will ever have (plus fun banter with Debby), we had the best experience. The suite is cozy, comfy, quiet, and private (we stayed in the Aquinnah suite), having a parking spot for our car was super convenient, and Charles had great recommendations for things to do and places to dine. It is our second time staying at Charles and Charles and we will definitely be back - highly recommend to anyone looking for a place to stay while visiting Martha's Vineyard.

My husband and I really enjoyed our stay for our wedding anniversary, the room was adorable with a very responsive host. Craig and Ginny were great, Craig gave us recommendations for a day trip to make the most out of our short 2 day trip, and we hit a lot of amazing highlights of the cape! We would love to come back one day!

This is my 20th summer traveling to the Vineyard. And I must admit, my stay at Kathleen's place has been the BEST!!!!!!!! Her place is clean, comfortable, and convenient to all the hot spots in Oak Bluffs. To top it off, I looked forward to the homemade scrumptious breakfast that Kathleen prepared each morning. Moreover, the accommodation comes with premium housekeeping services. Thus, Kathleen is the consummate host- staying at her place will make your Vineyard experience even more memorable.

Beautiful beach house with access to a private beach, kayaks, and the backyard. perfect for enjoying some time on the property and also touring around Falmouth and making a day trip at Martha's Vineyard. Lisa is a very warm and friendly host. You'll have a wonderful stay here!

Wonderful place, very clean, peaceful, and the owners were friendly, kind, available, and helpful. About 20 min walk to harbour with boats to Martha's Vineyard, and Nantucket. About 10 min walk to beach, and about 25 min walk to downtown shops. Big parking area, beautiful garden. I traveled all over the island but I found Hyannis being the center of things. I'd certainly recommend this place in Hyannis.

Charles is a great host! Our room was very comfortable with lots of nice touches (even snacks!), the property has beautiful gardens, and the location is quiet yet so convenient. Charles's poolside breakfasts were outstanding and a real highlight. This was our first time here and we hope to come back. Our best B&B experience ever!

Such an amazing stay in a beautiful historic home! Paul and Tracey were so accommodating. We had such an amazing time! Learned so much. Had a great breakfast. Parking right in front. Quiet and comfortable.

We had a great time! Loved the antique furniture, all the rich history. Our host (Paul) and innkeeper (Tracey) were wonderful - friendly, responsive and also very respectful of our privacy. Loved the king-size bed in the Sara Delano Room - sooooo comfortable!