Holiday rentals with beach access in Chilmark

Guest suite in West Tisbury

The main sleeping area features a spacious wooden bed with grey linens and two light blue towels neatly arranged on the bed. Two bedside tables with lamps flank the bed, and large windows with black shades provide a view of the greenery outside.

4.92 out of 5 average rating, 157 reviews

Studio Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this airy suite has vaulted wood ceilings with skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is prime and centrally located, just off historic Music St, a short walk to our small town center which provides many amenities. Ask about our other private guest suite if you are traveling with others

4.79 out of 5 average rating, 123 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.

Flat in Fairhaven

Main Street on the Park

Welcome to Main Street on the Park! The morning sun will greet you in the bright apartment in our big white house with a yellow front door. Perfect for a romantic getaway or a convenient place to stay if you are in the area for business. A large fenced yard abuts a public park complete with tennis courts, track and walking trail. Explore our small town with a big history, visit its historic buildings, great restaurants and unique shops. The location is convenient to all of the South Coast.

4.98 out of 5 average rating, 223 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.

Flat 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.

4.99 out of 5 average rating, 106 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.

Guest house in Chlmark

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.

5 out of 5 average rating, 106 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

4.91 out of 5 average rating, 129 reviews

The front exterior of the house is shown surrounded by lush greenery, featuring a well-maintained lawn. A pathway leads to the entrance, and the porch offers seating. Two sun loungers are positioned on the grass, inviting relaxation in the open space.

Home in Oak Bluffs

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home. Updated 7/25/2025 we do not have any more firewood on the property.

Guest suite in West Falmouth

A cozy living area features a comfortable gray sofa with decorative pillows and a wooden coffee table. Natural light fills the space, highlighting a dining table with four chairs. A doorway leads to the kitchen, while a wall-mounted TV provides entertainment options.

5 out of 5 average rating, 205 reviews

The Sea-Cret Garden, Guest Apartment

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

4.99 out of 5 average rating, 142 reviews

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.

Flat in Mattapoisett

Brand new! Whole apartment, huge tub, full kitchen

Beautiful self-contained apartment. Enjoy the blissful extra-long Kohler soaking tub, rain shower, and luxurious Matouk towels. Full kitchen and outdoor seating area. DreamCloud queen bed. Short walk to the center of the village and town wharf, providing easy access to all of Mattapoisett's charm, including Ned's Point Lighthouse and Town Beach. Outstanding local restaurants and sweet treats all close by.

5 out of 5 average rating, 203 reviews

An outdoor patio area is illuminated softly at dusk, featuring a dining set with a table and several chairs arranged on a patterned rug. Lush greenery and flowering plants surround the space, while lanterns provide a gentle glow, enhancing the tranquil environment.

Home in Mashpee Neck

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!

4.94 out of 5 average rating, 205 reviews

A bright living area features wooden beams across the ceiling and light walls. A comfortable couch with decorative pillows faces a coffee table stacked with magazines. Two lamps provide ambient lighting, while sunlight enters through multiple windows, creating a welcoming environment.

Cottage in East Falmouth

“Cozy Cottage” on Great Bay

Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach. We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

4.9 out of 5 average rating, 110 reviews

A view from the second-floor patio captures the bright sunlight reflecting off the water, with green park space across the street. Nearby houses frame the scene, and outdoor seating is visible on the patio, enhancing the inviting ambiance of the surroundings.

Home in Falmouth

Falmouth Heights Ocean Views & Steps to Beach

Prime location in Falmouth Heights!!! Steps from beloved Falmouth Heights Beach, the Black Dog Cafe, Shipwrecked, and the finish line to the Falmouth Road Race! We are also a short walk to the Island Queen Ferry to Martha's Vineyard, the Falmouth Yacht Club, and the delights of Falmouth's marvelous Main Street!

4.98 out of 5 average rating, 215 reviews

A two-story house is situated on a spacious lawn, featuring a wraparound porch adorned with planters of purple flowers. A grill is placed on the porch, and a pair of outdoor lounge chairs sits nearby under an umbrella, surrounded by trees and a clear blue sky.

Home in West Tisbury

West Tisbury Escape, Long Point Beach

2026 Calendar - Now Open! Our home is set on nearly 2 acres of land near Long Point Beach (the BEST beach & a great central location for exploring the island). Bright and sunny accommodation with wraparound porch, stone patio, outdoor shower and large yard. Comfortably sleeps 8 guests.

Popular amenities for rentals with beach access in Chilmark

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.95 out of 5 average rating, 333 reviews

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.

Flat in East Falmouth

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

4.88 out of 5 average rating, 164 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.

Flat in Oak Bluffs

WATERFRONT PENTHOUSE OAK BLUFFS

4.97 out of 5 average rating, 126 reviews

A spacious living area features a brick fireplace and a television. A comfortable sofa and armchairs are arranged around a coffee table on a patterned rug. A dining table with seating is visible in the background, along with decorative wall art and natural light from the windows.

Flat in Barnstable

Spacious & bright, near beaches

4.96 out of 5 average rating, 210 reviews

A neatly landscaped yard is visible, featuring a vibrant green lawn with two blue Adirondack chairs positioned in the foreground. Flowering plants and shrubs add color around the entrance of a welcoming blue house with a covered porch.

Flat in Portsmouth

Sweet Retreat by Mt. Hope Bay!

5 out of 5 average rating, 118 reviews

A private garden patio is showcased, featuring a circular table surrounded by four chairs. Plush cushions in vibrant blue patterns adorn the seating. Nearby, two wooden lounge chairs offer additional relaxation options. Lush greenery and flowers provide a natural backdrop, enhancing the outdoor ambiance.

Flat in Edgartown

Stylish retreat | walk to town | fire pit

4.96 out of 5 average rating, 344 reviews

Aerial view showcases a peaceful coastal neighborhood, with homes set against a backdrop of the ocean. The green lawns and sandy shore create a harmonious landscape. Soft clouds drift above, and the water glistens under natural light, enhancing the serene coastal environment.

Flat in Little Compton

Home by the Sea

4.85 out of 5 average rating, 141 reviews

A serene bay view is depicted during sunset, with gentle hues of orange and blue reflected on the calm water. Silhouettes of dock pilings line the shore, and a bare tree branch extends into the scene, adding a touch of natural framing.

Flat in Onset

⭐ Amazing Onset Getaway in the Starfish Suite

4.99 out of 5 average rating, 136 reviews

A living and dining area is presented with a circular table and four teal chairs. A dark sofa is positioned opposite a wall-mounted TV. Natural light enters through two windows, complemented by gray walls and modern light fixtures.

Flat in New Bedford

One Bedroom in-law near beach with breakfast

House rentals with beach access

4.89 out of 5 average rating, 62 reviews

The exterior of a charming shingled cottage is displayed, featuring a welcoming front porch with steps leading to the entrance. Green shutters flank the windows, and an American flag adds a patriotic touch. The surrounding grassy lawn enhances the home's inviting appearance.

Home in Edgartown

Updated Beautiful Cottage in Edgartown AC & Ferry

4.97 out of 5 average rating, 156 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

4.95 out of 5 average rating, 56 reviews

A bright living room features large windows offering views of the beach. Light-colored furnishings are complemented by a patterned area rug. A coffee table is centrally positioned, with decorative items placed atop. Two chairs provide additional seating, enhancing the open space.

Home in Fairhaven

Lovely Day Oceanside

4.98 out of 5 average rating, 218 reviews

A bright living area features hardwood flooring and large windows allowing natural light. A comfortable sofa and chairs are arranged around a wooden coffee table, with a decorative rug underneath. A television is mounted on the wall, complemented by coastal-themed decor.

Home in Portsmouth

3 BR -no guest fee-cozy beach house- near newport.

4.89 out of 5 average rating, 158 reviews

Home in Marstons Mills

Cape Cod Getaway - 3BR/2BA Beach Pass Included

4.93 out of 5 average rating, 209 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!

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

4.6 out of 5 average rating, 5 reviews

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.

Home in Chilmark

Private Chilmark Escape sleeps 6

Apartment rentals with beach access

4.55 out of 5 average rating, 70 reviews

An aerial view highlights the proximity of the cottage to Craigville Beach, visible at the bottom of the image. The layout of Southwinds Circle is seen nearby, along with several residential units, all situated along the beach shoreline, illustrating the tranquil seaside environment.

Apartment in Barnstable

Oceanside Cottage Apt next to Craigville beach

Apartment in South Yarmouth

The kitchen features wooden cabinetry and a stainless steel refrigerator. A gas stove is situated next to a black countertop with a sink. A small dining table with four chairs is present, along with a patterned rug on the floor.

4.74 out of 5 average rating, 141 reviews

Seaview Cottage

5 out of 5 average rating, 28 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.

Apartment in Oak Bluffs

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

Apartment in Vineyard Haven

A spacious pool area is enclosed by a white fence, surrounded by lush greenery. Lounge chairs are positioned around the edge of the inviting water, with trees and houses framing the scene in the background. The sky transitions to soft hues during sunset.

4.96 out of 5 average rating, 24 reviews

Relax....You're on Island Time......

Apartment in East Sandwich

A wooden boardwalk leads down to the sandy beach, framed by lush green grass and beach fencing. The calm ocean stretches out in the background under a slightly cloudy sky, creating a serene pathway to the shoreline.

3.8 out of 5 average rating, 5 reviews

103 N Shore Blvd #1 - Cozy E. Sandwich Beach condo

Apartment in Hyannis Port

A serene waterfront view features a wooden dock extending into calm waters, reflecting a colorful sunset with shades of orange and blue. Silhouettes of boats and poles can be seen against the horizon, enhancing the tranquil atmosphere.

4.82 out of 5 average rating, 17 reviews

Beachfront Complex in Hyannis

Apartment in East Sandwich

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.

4.9 out of 5 average rating, 52 reviews

Sandy Neck Provisions - Full Apartment