Up-Island: Ocean-Edged Pastoral Delights

For those seeking accommodations Up-Island, the 'bustle' of Oak Bluffs, Vineyard Haven and Edgartown are left behind in favor of the ocean-edged serenity of West Tisbury, Chilmark and Aquinnah. The owners of the inns, guest houses and bed-and-breakfasts in these towns pride themselves in offering guests respite from the fast pace of daily living by providing visitors with the chance to slow down and enjoy their time away from home.

Landmarks such as the famous Clay Cliffs, Menemsha Beach and Great Byte Rock are popular destinations. The rocking chairs on the porches of Alley's General Store and The Chilmark Store will earn you hearty conversations and new acquaintances. The Field Gallery with its garden full of stone sculptures, John Belushi's shrine, the views from Peaked Hill and limited access beaches are just a few of the reasons why this end of the Island is such a desired vacation location. A trip to Chilmark Chocolates, the Island's own premier chocolatiers, is not to be missed. If you're a runner, participating in the annual Chilmark Road Race will help raise money for charitable causes.

Staying Up-Island involves some planning. For the most part, those who choose to stay on the outer edges of the Island bring their cars or make arrangements to rent a car or motor-scooter once they arrive at Martha's Vineyard. In some cases public transportation and taxi services will meet guests' travel needs as they vacation where as other times, bicycle enthusiasts pedal up the winding steep roads of Chilmark, Aquinnah and West Tisbury to check into the accommodation of their choice.

Please, browse the Property Descriptions and corresponding Property Numbers. Select an accommodation that you would enjoy the most and go to the ‘Book Me Now’ screen to file your request. For a full list of things to do and up-coming events, read the ‘Don’t Miss Out’ page of this site. Keep in mind that every property in West Tisbury, Chilmark and Aquinnah is a non-smoking establishment unless stated otherwise.

Property Number Forty-Six This romantically secluded bed and breakfast is located amidst the meadows of West Tisbury. Each of the five bedrooms has a distinct personality which is enhanced by antique furnishings and private baths. Canopy beds dressed with cozy quilts and hand-made lace pillows highlight these comfortable rooms. A full gourmet breakfast is prepared every day and is centered around a special main dish. The inn offers complimentary beach passes to the private soft sand beach of Lambert's Cove. It’s a wonderful place for couples, small get-togethers, intimate bridal parties and retreats.

Property 46

Property Number Forty-Seven Surrounded by the tranquility of the Lambert’s Cove area and apple orchards, portions of this bed-and-breakfast estate date back to the eighteenth century. Comprised of a main building, several outlying buildings and an outdoor pool, this property has been recently renovated to showcase the owners' love for the Florida Keys and Martha’s Vineyard. An award winning restaurant shares the main building and serves dinner nightly. All rooms include private bath, cable-color television, air-conditioning, data ports/wireless internet (charges may apply) and daily continental breakfast. Complimentary passes to the private beach of Lambert's Cove are also included.

Property 47

Property Number Forty-Eight This unique cottage-inn in Menemsha sits on ten acres of gardens and woodlands. Ocean vistas offer breathtaking panoramic views of Chilmark sunsets and moss covered stonewalls accentuate the property. Open seasonally, it’s just a short walk to the quaint fishing village of Menemsha. Accommodations vary; guests can choose between six elegant luxury suites, nine superb inn rooms, and twelve charming housekeeping cottages. Fully functional wood burning fireplaces add a romantic touch to the cottages.

Property 48

Property Number Forty-Nine Extremely affordable and located between Martha’s Vineyard Airport and Alley’s General Store, this friendly three-room bed and breakfast is simply furnished with either one double or two twin beds in the guest rooms. Casual and comfortable, the house has "yards of yard" and is in a very quiet area of West Tisbury. Children are welcome and there are no private baths. A home-made continental breakfast is offered every morning.

Property 49

Property Number Fifty Sitting just behind the Gay Head Lighthouse, this bed-and-breakfast is one of the Vineyard's most premier properties as much as it is an unadvertised treasure. Personal touches throughout the building match the attention to detail that spans everything from breakfast ingredients to evening turn-down service. An award winning restaurant serves dinner nightly and it's important to secure reservations early for both rooms and tables as there are only five guest rooms and the restaurant seats a maximum of thirty people. Acres of gardens, extradinary ocean views and the option of booking an excursion on the boat owned by the property makes a stay at this bed-and-breakfast truly memorable. Because of the couples-only nature of this property, it is not prepared to host guests under the age of sixteen.

Property 50