Vacation rentals with beach access in Chilmark

An open living room features a large sectional sofa arranged around a coffee table. A stone fireplace is positioned against a brick wall, with warm wood beams overhead. Natural light floods the space through expansive windows, showcasing a wooden floor.

4.71 out of 5 average rating, 7 reviews

Private Chilmark Escape sleeps 6

Great retreat for a family/group in this light-filled private house w a spacious mahogany deck. Waskosim's Rock Res/passes to Lucy Vincent/Squibnocket- by presenting your lease at town hall. Tennis @ private assoc courts.Midcentury modern w all-wood cathedral ceilings. Open-floor-plan living room has huge sectional/Smart TV/Mini splits .All-new kitchen has natural soapstone countertops, Bosch fridge/dishwasher. In 2026 the entire interior was freshly painted and the carpeting downstairs is new.

A cozy living area features a light-colored sofa adorned with cushions next to a wooden table. Sunlight filters through window shades, illuminating the space. A vintage wooden box holds a bouquet of flowers, while wicker chairs provide additional seating, creating a relaxed atmosphere.

5 out of 5 average rating, 26 reviews

The Blueberry House on Martha’s Vineyard

Welcome to 'The Blueberry House' in Chilmark, up-island in beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. This 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road next to North Tabor Farm with quick access to Great Rock Bight preserve, Menemsha Beach and Chilmark Store. Multi-week stays require weekly cleaning $300 each.

An outdoor deck with a wooden dining table and matching chairs is shown, illuminated by a vibrant sunset. Lush greenery and the neighboring buildings can be seen in the background, creating a peaceful setting for dining al fresco.

4.98 out of 5 average rating, 46 reviews

Fun, Authentic, Waterfront Cottage/air conditioned

This authentic beach cottage is centrally-located in the fishing village of Menemsha with stunning views of the sunset, the harbor, the beach and Menemsha Creek. Charter a fishing boat in the harbor across the street or spend the day on the beach just a few steps away. As you meander back to the house, pick up fresh fish to grill on the deck or pre-cooked lobsters and steamers. If you prefer to eat out, rinse off in the outdoor shower and take a walk around the corner to dinner with a view.

4.93 out of 5 average rating, 221 reviews

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

An enclosed front porch features multiple windows providing a view of the surrounding greenery. Two rocking chairs are positioned on a patterned rug, alongside a wooden table and lamp. Natural light fills the space, creating a bright and open atmosphere.

4.98 out of 5 average rating, 60 reviews

Renovated pond view home near Lamberts Cove beach

Idyllic renovated farmhouse across from Seth's Pond and 0.6 miles from the infamous Lamberts Cove beach. Enjoy the views from the expansive enclosed front porch, play in the 2 acre yard and relax on the back patio with hardlined gas grill. Renovated kitchen, many recent renovations and a fully stocked home ensure a comfortable stay. Terrific mid-island location with easy access to nature hikes, State Road Restaurant, the Lamberts Cove Inn Restaurant, Up Island Cronigs (groceries) and more!

Guest suite in West Tisbury

A spacious guest suite is illuminated by natural light from multiple skylights. The room includes a comfortable queen size bed with crisp linens, a sitting area with a light-colored couch, and a coffee table. Wood flooring adds warmth to the inviting atmosphere.

4.94 out of 5 average rating, 176 reviews

The Loft Guest Suite. Private. Newly Renovated.

This beautiful guest suite is a 5 minute walk to the village of West Tisbury on Martha’s Vineyard and has a private entrance on the 2nd floor of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, a short walk to a village, providing amenities. Ask about our other guest suites if you are with others.

4.99 out of 5 average rating, 113 reviews

The open living area features exposed wooden beams overhead and includes a spacious wooden dining table. Two lounge chairs, a round pouf, and a day bed are arranged for seating. Natural light filters in through large glass doors, leading to an outdoor area.

Guesthouse in Chilmark

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

The image captures a panoramic view of the ocean, surrounded by lush greenery. The tranquil blue water extends to the horizon, with a distant lighthouse visible on a rocky coastline. A clear sky overhead enhances the natural beauty of the landscape.

4.96 out of 5 average rating, 107 reviews

Lambert's Cove Oceanview FERRY Tikts See descript

Car FERRY TKTS avail. for purchase for weeks 7/4/26, 7/11/26, and 7/18/26. Salt box home set in the forested hills above Lambert's Cove. Short walk / drive to town beach. Perfect for family gatherings, home has 3 bedrooms , loft for virtual work space or reading room, 1.5 baths plus the fully enclosed outdoor shower, fully stocked kitchen, a deck that has seating for relaxing and also an octagonal picnic table, as well as lots of yard space for children or pups to play.

A well-lit room features tall windows providing views of the outdoor deck. A wooden desk and chair are positioned next to a seating area, which includes an armchair and a floral-patterned chair. Bookshelves line the walls, and vibrant artwork decorates the space.

4.98 out of 5 average rating, 90 reviews

Peaceful Retreat Near Up-Island Beaches

Welcome to our charming 2-bedroom private guest house, nestled in a peaceful Chilmark neighborhood. Enjoy the spacious outdoor area, perfect for gatherings, featuring an 8-person dining set, a wood-burning fire pit, a BBQ grill and a seasonal outdoor shower. Our location offers easy access to local attractions: just a 4-minute drive to Alleys General Store, West Tisbury Center, and the library, and only 5 minutes to the stunning Lucy Vincent Beach and Chilmark town center.

Guest suite in Oak Bluffs

A spacious outdoor deck features wooden furniture, including a dining table with chairs and lounge seating. An umbrella provides shade, and potted plants enhance the natural setting. The deck is surrounded by greenery, contributing to a serene outdoor atmosphere.

4.79 out of 5 average rating, 346 reviews

Cottage suite between the harbors: no minimum stay

Nestled between Oak Bluffs and Vineyard Haven harbors, our relaxing suite is a perfect way to extend your weekly rental, or to enjoy a day or two on this special island we call The Rock. Our cozy guest suite, newly renovated has two bedrooms, living space, kitchenette, full bath, deck with grill, outdoor shower, and footwash (hot H20), W/D (in unit) and a private entrance. An easy walk to town and beaches. Parking is available in our driveway. Enjoy our historic home!

5 out of 5 average rating, 166 reviews

A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.

Home in Falmouth

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

4.94 out of 5 average rating, 120 reviews

A historic lighthouse stands beside a renovated white keepers home, both set on a lush green lawn. The Atlantic Ocean stretches out in the background under clear blue skies, offering a serene coastal view.

Lighthouse in Pocasset

Wings Neck Lighthouse

Once in a lifetime experience to stay in a Lighthouse. Historic, unique and charming but with all of the conveniences that make a great vacation. Just feet from the Atlantic with 360 degrees of ocean view. Beautiful, peaceful and memorable all year long. Sandy private association beach just steps away. Expansive lawn and patio for enjoying salt air, waves, boats and sunsets.

Popular amenities for Chilmark beach access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

Apartment in Sagamore Beach

A bright living area features a large window that allows natural light to fill the space. Comfortable seating includes a gray sofa and a dark blue loveseat. A wooden coffee table sits between them, and a ceiling fan helps maintain a comfortable temperature.

4.98 out of 5 average rating, 126 reviews

Cape Cod Canal Home

Apartment in East Falmouth

A functional kitchen space is equipped with essential appliances, including a stove, microwave, and toaster. Wooden cabinetry houses various kitchenware. The layout features a countertop with a dish rack and a small step stool beneath. Soft lighting creates a welcoming atmosphere.

4.95 out of 5 average rating, 339 reviews

In-law apt. with all the amenities of Home.

4.89 out of 5 average rating, 170 reviews

A charming waterfront building with a distinct blue facade features multiple balconies lined with railing. A lively outdoor dining area is visible on the lower level. Surrounding structures reflect a lively coastal atmosphere, with clear skies and people enjoying the vibrant setting.

Apartment in Oak Bluffs

WATERFRONT PENTHOUSE OAK BLUFFS

Apartment in Mattapoisett

A modern kitchen is showcased, featuring navy blue cabinetry and wooden countertops. Equipped with a stainless steel refrigerator, oven, and a farmhouse sink, the space includes a toaster and coffee maker. Shelves display dishware, while bright light enhances the welcoming atmosphere.

4.99 out of 5 average rating, 168 reviews

Brand new! Whole apartment, huge tub, full kitchen

4.92 out of 5 average rating, 210 reviews

An aerial view highlights the scenic Onset area, showcasing the nearby beach and water bodies. The renovated Sea Captain's house is marked, surrounded by a largely residential neighborhood with streets leading to the coastline.

Apartment in Wareham

☀️ Spacious and Bright -- The Sailboat Suite

4.92 out of 5 average rating, 145 reviews

A kitchen area features a bar with three wooden stools, inviting casual dining. Hanging pots and pans are showcased above the counter, while a vase of red roses adds a touch of color. A brick wall complements the white cabinetry and appliances.

Apartment in Tisbury

Harbor view apartment, a quick walk from the ferry

4.79 out of 5 average rating, 130 reviews

A cozy living area is presented with a dark couch and a wooden dining table accompanied by black chairs. A TV is situated on a light-colored media unit, while bookshelves filled with books line one wall. Natural light filters in through sheer curtains.

Apartment in Fairhaven

Main Street on the Park

4.98 out of 5 average rating, 235 reviews

An open studio space features a cozy sleeping area with a spacious bed covered in light bedding. A soft armchair and a wooden bench provide additional seating. Natural light streams in from a window, enhancing the room's bright atmosphere. Shelving displays books and decorative items.

Apartment in Oak Bluffs

Sunny Studio Apartment on Martha's Vineyard

House rentals with beach access

The timberframe house features shingle siding and multiple large windows, inviting natural light. A spacious deck is visible, surrounded by lush vegetation, including flowering plants. The exterior is set against a backdrop of trees, enhancing the natural appeal of the property.

4.98 out of 5 average rating, 42 reviews

Tucked away Up Island

A cozy living area is highlighted by high, exposed wooden beams and a stone fireplace. Two patterned armchairs and a gray sofa are arranged on an area rug, while a circular wooden coffee table holds decorative items. Natural light filters through the windows, enhancing the warm ambiance.

5 out of 5 average rating, 9 reviews

3BR Home, Fenced Yard, Free use of car, Pets ok!

4.96 out of 5 average rating, 291 reviews

The exterior of a charming carriage house is framed by lush greenery and colorful plants. A well-maintained garden surrounds the building, highlighting vibrant flowers and a small Japanese maple. Natural stone pathways guide toward the entrance, enhancing the serene setting.

Home in Falmouth

Newly renovated garden carriage house

The cottage exterior is framed by neatly trimmed shrubs and features a screened-in porch with multiple windows. A peaked roof caps the structure, which is surrounded by greenery and offers a glimpse of the clear blue sky above.

4.88 out of 5 average rating, 8 reviews

Path to Menemsha Beach

A charming waterfront cottage is depicted, featuring a light gray shingle exterior and a welcoming entryway with wooden steps. The expansive ocean view is visible in the background, enhancing the serene landscape, with clear skies and greenery surrounding the property.

4.86 out of 5 average rating, 69 reviews

Cozy Waterfront Cottage, Newly Remodeled!

4.99 out of 5 average rating, 155 reviews

The exterior of a spacious coastal property is shown, featuring a wraparound porch and light grey shingle siding. A clear blue sky complements the beach setting, with soft sand leading to the ocean in the background. Lush greenery borders the property, providing a sense of seclusion.

Home in Sandwich

Salt Eire | Oceanfront Beach Home

4.92 out of 5 average rating, 165 reviews

A modern kitchen is showcased, featuring stainless steel appliances and a large island with seating. Natural light fills the space through a patterned curtain, complementing the blue and white decor. A cozy seating area includes a light-colored sofa and a coffee table, enhancing the room's functionality.

Home in Edgartown

✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path

A spacious two-story home is framed by expansive lawns and lush greenery. The exterior features a mix of wood siding and gray roof, while a garden and outdoor seating area enhance the inviting setting. A sunny sky and tree foliage provide a peaceful backdrop.

4.92 out of 5 average rating, 13 reviews

1800s Farmhouse | Sanctuary Trails | Pickleball

Condo rentals with beach access

5 out of 5 average rating, 32 reviews

A serene view of the ocean is framed by white wooden architecture. The calm water reflects a clear blue sky, while a sandy beach lies in the foreground, accompanied by a stone jetty. Benches are positioned along the walkway, inviting relaxation.

Condo in Oak Bluffs

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

4.83 out of 5 average rating, 53 reviews

A round black table is positioned between two comfortable chairs adorned with patterned upholstery. Atop the table, a decorative floral arrangement includes blue and white flowers, complemented by greenery. A couple of neatly stacked books are also visible.

Condo in Oak Bluffs

Serenity on Martha's Vineyard

Superhost

An aerial view of a beachside condo property is shown, highlighting the proximity to East Sandwich Beach. The two-story building is marked as Unit 1, featuring a shingle exterior with large windows. The sandy beach is visible in the background, inviting for beach activities.

Condo in Sandwich

3.83 out of 5 average rating, 6 reviews

Charming Cape Condo Steps to Private Beach

A bright living area features large windows that allow natural light to fill the space. A light-colored sectional sofa is complemented by a chaise lounge and a wooden coffee table. A patterned area rug anchors the seating area, while tropical plants add a touch of greenery.

Condo in New Seabury

4.93 out of 5 average rating, 15 reviews

Private Ocean Overlook! Serene Cape Cod Escape

4.87 out of 5 average rating, 47 reviews

A welcoming outdoor seating area is furnished with a white sofa and dark wicker chairs, complemented by yellow accents. A patterned rug lies beneath, and an umbrella provides shade, creating an inviting spot for relaxation among trees and natural surroundings.

Condo in New Seabury

Cape Esacpe at New Seabury

4.73 out of 5 average rating, 30 reviews

A bright living area features a navy blue sectional sofa and a wooden dining table with four chairs. Light streams in through a large window adorned with green curtains, complementing a coastal-themed wall art piece. A cozy area rug lies beneath a wooden coffee table.

Condo in Tisbury

Heart of VH, w/ac, pool & harborview

4.91 out of 5 average rating, 54 reviews

A cozy bedroom features a spacious bed with a light-colored quilt and multiple pillows. Two nightstands with soft-glowing lamps flank the bed, enhancing the serene atmosphere. A comfortable armchair is positioned next to a window, allowing natural light to fill the room.

Condo in Sandwich

Sandy Neck Provisions - Full Apartment