Holiday rentals with beach access in Chilmark

Guest house in Centerville

A charming carriage house with shingle siding is set against a blue sky adorned with fluffy clouds. A black Jeep is parked in front, showcasing the gravel driveway. Lush greenery surrounds the property, enhancing its inviting appearance.

5 out of 5 average rating, 146 reviews

Modern Fireplaced Carriage House with Beach Permit

Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

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

4.94 out of 5 average rating, 131 reviews

A cozy family room features a slip-covered sofa and two light-colored armchairs, arranged around a wooden coffee table. A brick fireplace complements the space, and a flat-screen TV is mounted above it. Light from the window illuminates the warm wooden flooring.

Home in Mashpee

Newly Renovated! Seconds to sand, fire pit, A/C

Recently Renovated! This Cape Cod Cottage is completely refreshed top to bottom. Less than 60 seconds to the sand. Cape cod vacations do not get any better than this! Located on idyllic Monomoscoy Island known for its gorgeous wildlife and stunning waterways, our home is the perfect choice to rent on Cape Cod. We are less than 10 Mins to Mashpee Commons and famous Mashpee Town Beach, Less than 5 mins to New Seabury and the Popponesset Inn, and only 15 mins to downtown Falmouth. Linens 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!

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!

4.9 out of 5 average rating, 178 reviews

A charming cottage exterior is surrounded by lush greenery and blooming rose bushes, with a white picket fence enclosing the front yard. The gabled roof and shingle siding complement the tranquil landscape, offering a welcoming first impression.

Cottage in New Seabury

Quaint Cape Cod Cottage on a Private Beach!

Create magical memories on the Cape at this sweet seaside cottage! A perfect place for a family-friendly getaway or a romantic retreat for two! The new contemporary coastal decor is cozy and comfortable and my place has all of the amenities you could want for your stay! Just steps to a beautiful beach with stunning sunsets and sunrises, cool ocean breeze, and the warm Nantucket Sound. Enjoy Popponesset Marketplace for food, shopping and fun or take a short drive to Mashpee Commons for more!

4.79 out of 5 average rating, 121 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 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.

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.

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

One bedroom in-law apartment with Queen size bed, and Queen sleeper sofa in the living room. Full kitchen and 3/4 bathroom. Close to downtown New Bedford with many restaurant options, and ferries to Martha's Vineyard, Nantucket and Cuttyhunk. Short walk to the beach (1/4 mile), Fort Rodman and Fort Taber where there is a military museum and a walking/bike path. Flexible Check-in, so you can arrive when convenient for you (as early as 9AM). No Guests or parties.

Guest suite in West Falmouth

A serene view of a spacious home set against a backdrop of lush greenery and wildflowers. The house presents an inviting facade with multiple windows, surrounded by the natural beauty of the landscape, creating a sense of tranquility.

4.99 out of 5 average rating, 213 reviews

The Ideal Spot

The perfect getaway in Falmouth for all seasons! Our home is beautifully located overlooking Bourne’s Farm and we are steps away to the picturesque Shining Sea Bike Path. Enjoy a beautiful scenic 8.5 mile ride winding your way thru the Sippewisset marsh and along the coastline to the seaside village of Woods Hole. Where you can enjoy the local restaurants ,shops and science learning or jump on the ferry to Marta’s Vineyard.

4.99 out of 5 average rating, 140 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.

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

4.73 out of 5 average rating, 103 reviews

The building exterior features a pastel pink facade with white trim. Double front doors are flanked by two circular bay windows, allowing natural light inside. The structure is sparsely landscaped, with a concrete walkway leading to the entrance.

Flat in Hyannis

Perfect Location for a Walking Vacation

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

4.78 out of 5 average rating, 221 reviews

Flat in Oak Bluffs

Sunny Private studio amazing deck kayaks & kitchen

4.71 out of 5 average rating, 28 reviews

An outdoor patio area is surrounded by lush gardens featuring blooming flowers and greenery. Two blue chairs are positioned near a table underneath a large umbrella, providing a shaded space for relaxation. The backdrop includes a well-maintained building with multiple glass doors.

Flat in Aquinnah

Quiet & Serene in Aquinnah

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

House rentals with beach access

4.94 out of 5 average rating, 54 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

4.89 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, 151 reviews

A spacious living area is shared between a large wooden dining table and a comfortable seating arrangement. A textured light fixture hangs above the table, while a television is mounted in the background. Windows allow natural light to fill the space, enhancing the open feel.

Home in Barnstable

Cozy 1-level fenced yard Craigville Beach 2000sqft

4.89 out of 5 average rating, 61 reviews

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.

Home in Chilmark

Cozy Waterfront Cottage, Newly Remodeled!

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

4.91 out of 5 average rating, 163 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

4.93 out of 5 average rating, 60 reviews

An open floor plan is depicted, featuring a light-filled living area with a beige sofa and a natural wood coffee table. The kitchen shows a large island with bar stools and sleek appliances, while a dining table is positioned beside sliding doors leading to the outdoors.

Home in Teaticket

Renovated house close to everything

4.95 out of 5 average rating, 126 reviews

A light-filled living room is showcased with a comfortable sofa, side chairs, and a flat-screen TV. A brick fireplace is centered in the room, adorned with a round mirror and decorative items. Natural light filters through the windows, enhancing the inviting space.

Home in Edgartown

Walk To Town - Beautiful Edgartown Cottage

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 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......

5 out of 5 average rating, 8 reviews

A two-story building designed in a classic Cape Cod style is showcased, featuring a large balcony on the front. Lush green landscaping surrounds the building, enhancing the tranquil outdoor setting. Nearby structures are visible, displaying similar architectural features.

Apartment in Falmouth

Beachside Villiage-Oceanfront

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.

Apartment in New Seabury

4.93 out of 5 average rating, 14 reviews

Private Ocean Overlook! Serene Cape Cod Escape

4.97 out of 5 average rating, 33 reviews

A light blue condominium building stands prominently along a paved road leading to the shoreline. The ocean is visible in the background, with a sandy beach accessible via a pathway. A clear blue sky enhances the serene coastal atmosphere.

Apartment in Oak Bluffs

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Apartment in Vineyard Haven

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.

4.73 out of 5 average rating, 26 reviews

Heart of VH, w/ac, pool & harborview

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