Holiday rentals with beach access in Chilmark

4.95 out of 5 average rating, 99 reviews

The exterior of the barn features wooden double doors that provide access to the interior. A stone wall runs along the garden, accompanied by seating areas consisting of a picnic table and two chairs. Lush greenery surrounds the property, enhancing the secluded feel.

Guesthouse in Chilmark

Beautifully Renovated 1800s Chilmark Barn

Beautiful 2-story private barn in Chilmark on Martha's Vineyard. Secluded yet convenient. Perfect for a couple or a couple with older children (space not good for those with mobility issues). Downstairs living area, dining area, fridge, toaster, coffee maker, half bath -- shower is outside in the private garden. Loft-style sleeping area upstairs (2 private sections). 2 friendly labs and 5 chickens on premises. Walk to Chilmark Store, easy bus access. Walk-on pass to town beaches, no car pass

5 out of 5 average rating, 27 reviews

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.

Home in Chilmark

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.

4.98 out of 5 average rating, 48 reviews

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.

Home in Chilmark

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!

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, 180 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.

4.93 out of 5 average rating, 332 reviews

A serene view of the Westport River at dusk features soft pastel hues reflecting on the water. A wooden dock extends into the calm river, framed by gentle grasses in the foreground. The sky transitions from deep blue to warm oranges and yellows as the sun sets.

Cabin in Westport

Koselig Cabin on the Farm Coast of New England!

This cabin is full of comforts, convenience, and love. Just 4 miles from the ocean. It is located under a mile to Buzzards Bay Brewery and Westport Rivers Winery and a 5 minute walk to the quiet little neighborhoods private beach on the East Branch of the Westport River. Koselig embodies feelings of family, friends, warmth, love, coziness, contentment, and comfort. We have a custom area and house guide at the Cabin with everything you need to know to maximize your experience in the area!

4.98 out of 5 average rating, 236 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

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

5 out of 5 average rating, 115 reviews

A sandy beach stretches along the shoreline, meeting the calm blue waters. People are seen enjoying the sun and swimming. Beach umbrellas and some distant structures are visible under a clear sky with a few clouds.

Guest suite in Falmouth

Location Location Location! Beach, Bike, Ferry

STEPS to beach, bike path, trails, restaurants, shopping, bus to MV Ferry Gorgeous studio/in law apartment, private entry, own parking + patio Open plan living/sleeping area + en suite bathroom Queen bed + queen sleeper sofa: sleeps max 4 Fresh linens, towels, personal care products, first aid, hairdryer, iron Mini kitchen w fridge, air fryer, microwave, toaster oven, dishwasher, cutlery, crockery, coffee maker Our famous home baked goodies! Coffee/tea/milk/sparkling water provided

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, 109 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.

4.98 out of 5 average rating, 92 reviews

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.

Home in Chilmark

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.

4.79 out of 5 average rating, 358 reviews

A cozy seating area is featured with a gray sofa adorned with textured pillows and a light throw. A light curtain softly filters natural light, and a wooden shelf holds decorative items. A beach-themed sign adds a subtle touch to the sunny space.

Cottage in Fairhaven

On the Beach Cottage in Fairhaven

Enjoy your own private beach at our comfortable Beach Cottage. Hop on the local bike rentals to the nearby soda shop for snacks and treats. Or throw a line in for the days fresh catch. Spend some time relaxing on the back deck overlooking the saltwater marsh. After a day of searching for Sea glass and building sand castles on your own beach you will fall right asleep to the sounds and smells of the ocean right outside your bedroom patio doors. Welcome to your vacation

5 out of 5 average rating, 167 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.

Popular amenities for Chilmark Accommodation with Beach Access

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, 345 reviews

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

4.89 out of 5 average rating, 174 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, 173 reviews

Brand new! Whole apartment, huge tub, full kitchen

4.92 out of 5 average rating, 212 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, 146 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, 131 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

4.91 out of 5 average rating, 172 reviews

A spacious bedroom is showcased with a large bed featuring soft linens and decorative pillows. A comfortable armchair, table lamp, and an electric fireplace contribute to the inviting atmosphere. Light-colored walls and hardwood floors enhance the room's aesthetic.

Apartment in Somerset

The Crows Nest - 1747 Isaac Pierce House 2nd Floor

Holiday House Rentals with beach access

4.97 out of 5 average rating, 165 reviews

The exterior of a charming multi-level home is showcased, featuring a spacious deck with seating and an umbrella. A stairway provides access to the upper level, surrounded by lush greenery. Large windows offer views of the wooded surroundings, creating a sense of integration with nature.

Home in Falmouth

Mid-Century Modern home 5 minute walk to beach

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, 43 reviews

Tucked away Up Island

4.93 out of 5 average rating, 27 reviews

The image presents a charming two-story house surrounded by a well-maintained lawn. A spacious deck features white railings, offering an area for relaxation. The house showcases multiple windows that enhance natural light, and the clear blue sky above adds to the serene atmosphere.

Home in Westport

Sunny beach house with beautiful ocean views.

4.82 out of 5 average rating, 39 reviews

The dining area features a round wooden table surrounded by four black and natural chairs, with a tasteful floral arrangement at the center. Large glass doors provide a view of the ocean, and a cozy living space with a gas fireplace is visible in the background.

Home in Pocasset

Pocasset Private Beach Family Retreat/firepit

4.83 out of 5 average rating, 18 reviews

A cozy cottage is surrounded by a spacious lawn, with large windows reflecting natural light. The wraparound porch offers access to the outdoors, framed by trees and greenery. A small fire pit can be seen on the lawn, contributing to the peaceful ambiance.

Home in Aquinnah

Secluded Aquinnah Cottage

An open-plan living and dining area offers vaulted ceilings and ample natural light. A large wooden dining table is surrounded by black, spindle-back chairs. A sectional sofa in a muted blue color is positioned nearby, with sliding glass doors leading to an outdoor deck.

4.94 out of 5 average rating, 17 reviews

Private 5BR Vineyard Retreat - Peaceful & Central

4.98 out of 5 average rating, 55 reviews

A charming two-story house is featured, showcasing shingle-style architecture and a welcoming front porch. White pillars support a broad balcony, while large windows allow for natural light. The well-maintained exterior is accented by a well-paved path and surrounding greenery.

Home in Oak Bluffs

Pinkletink Plantation

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

Holiday condos with beach access

5 out of 5 average rating, 34 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

4.82 out of 5 average rating, 55 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

3.83 out of 5 average rating, 6 reviews

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

103 N Shore Blvd # 1

4.67 out of 5 average rating, 9 reviews

An aerial view captures the resort's layout alongside the coastline. Sandy beach stretches along the water's edge, while the Atlantic Ocean meets a calm bay. Behind the resort, residential areas are interspersed with patches of greenery, illustrating the natural beauty surrounding the location.

Condo in Falmouth

InnSeason Resorts Surfside

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

4.88 out of 5 average rating, 17 reviews

Private Ocean Overlook! Serene Cape Cod Escape

4.71 out of 5 average rating, 31 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

4.84 out of 5 average rating, 57 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