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!

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.

The hosts were friendly and the cozy apartment was ideally located for our stay. It was private and quiet, and we appreciated the in- unit washer/dryer, refrigerator and microwave.

We stayed at Wiz's place for 3 nights and felt right at home! Our stay was super pleasant, there are a lot of things to do in the area and we could have stayed a lot longer. The breakfast was such a nice little touch and the homemade goodies were very much appreciated! Thanks again for everything!!

Absolutely love our stay! The white room was beautiful and exactly as described! The bed was extremely comfortable and I loved the lounging chair for reading. The outside balcony was wonderful to sit on. The bike/walking bath was very accessible and provided a great afternoon of walking. The Knob recommendation was breath taking! Thank you for your morning conversations and getting to know you!! Definitely would recommend this bed and breakfast!

This is a great rental for anyone coming to MV. Its nice, quiet, tranquil and away from the noise of dowtown. The unit was clean, in perfect condition, along with snacks a bottle of wine. The pool was nice and cool, and the bikes provided were a nice touch to get around town. Breakfast the next morning was perfect and tasty, we loved it. I highly recommend Charles and Charles as a place to stay.

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.

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.

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!

We had an amazing stay at Kathleens Cottage. Both her and Frank were amazingly friendly hosts. The accommodation is spacious with bedroom, living area and bathroom - all spotless. The bed was huge and extremely comfortable. Added bonus here are the wonderful breakfasts each morning where Kathleen treats you to her daily bakes (banana/pecan and coffee cakes were delicious) plus soufflé etc... each morning she had something different. It was so relaxing to sit outside in the decked garden area each morning enjoying breakfast and chatting, getting great recommendations of what to do and where to go and was the perfect start to what were busy and enjoyable days exploring this beautiful island. Frank and Kathleen gave us great recommendations for places to eat and even gave advice on where to go for our next stop in the itinerary (Newport, Rhode Island - their recommendations were again 100% spot on). Thanks both for being such great hosts. 100% recommend this place