House holiday rentals in Chilmark

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, 24 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.

Superhost

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.

4.6 out of 5 average rating, 5 reviews

Private Chilmark Escape sleeps 6

Great retreat for a family or group in this light-filled private deck house. Comfortable furnishings w a spacious mahogany deck. Beautiful Waskosim's Rock Res/passes to Lucy Vincent/Squibnocket- by presenting your lease at town hall. Tennis at private assoc courts.Midcentury modern w all-wood cathedral ceilings. The open-floor-plan living room has a huge sectional/Smart TV .The all-new kitchen (2023) has natural soapstone countertops, Bosch stainless steel fridge/dishwasher. Mini-splits w A/C

A clear view of Vineyard Sound is visible through the surrounding trees, showcasing the serene blue waters extending to the horizon. The gentle outlines of land can be seen in the distance, framed by lush greenery and a tranquil atmosphere.

4.97 out of 5 average rating, 118 reviews

Lambert's Cove, Water view, Beach pass, Ferry Tix

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

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, 41 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.

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, 58 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. Brand new 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!

A spacious living area features a large sectional sofa and a coffee table, creating a comfortable gathering spot. Light filters in through two large windows, illuminating the warm wood flooring. A dining area is visible in the background, and framed artwork decorates the walls.

4.85 out of 5 average rating, 66 reviews

Chilmark Cape in private wooded setting

A renovated country home located in the Vineyard's most idyllic town. This 4 bed/2 full bath home offers you an updated kitchen, open living area, spacious bedrooms, outdoor shower, private back deck, and grassy yard on 3 wooded acres. Staying in Chilmark allows you access to the best beaches on the island. 2026 Season: Reminder that ferry tickets are the responsibility of the tenants. Our guests can obtain a sticker for access to Lucy Vincent Beach Pets permitted w/some restrictions.

A gravel driveway leads to a charming house with a red garage. A wooden pergola, adorned with greenery, provides shade along the entrance. Lush trees and open sky enhance the serene outdoor setting, inviting visitors to explore the surrounding landscape.

4.96 out of 5 average rating, 56 reviews

Vineyard Meadow Writer's Cottage with Hot Tub

This lovely retreat is just steps from miles of trails. Walk to the beach or meander through woods of Long Point Wildlife Refuge, experiencing the serenity of this untouched corner of Martha's Vineyard. After a day of enjoying the outdoors, come home to the light and airy writer's retreat. The HOT TUB IS OPEN! It also has an outdoor shower and a wonderful kitchen. This is the perfect location for a get-away with family and friends or for a creative retreat with your fellow artists.

4.93 out of 5 average rating, 128 reviews

A spacious deck features two wooden Adirondack chairs facing a serene waterfront view of Vineyard Sound. Lush greenery surrounds the area, and the calm water reflects the soft hues of the sky, creating a peaceful outdoor setting.

Home in Woods Hole

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on a quiet semi-private road with beautiful views of Vineyard Sound. This inviting coastal retreat features 3 bedrooms, 2 private en-suite baths, 1 semi-private en-suite bath, a fully equipped kitchen, gas fireplace, cable TV, WiFi, and air conditioning. Relax on the second-floor deck with water views or enjoy outdoor dining on the patio with the BBQ grill. Conveniently located near the Martha’s Vineyard ferry, bus station, beaches, shops, and town.

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, 102 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, 88 reviews

2 BR-Private guest house

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.

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

4.92 out of 5 average rating, 303 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

A raised ranch is surrounded by lush greenery, with large windows allowing natural light to fill the interior. A spacious deck extends from the front, providing outdoor seating options. The home is elevated, partially obscured by surrounding trees, and features a charming sloped roof.

4.79 out of 5 average rating, 254 reviews

Central location for your vacation

An apartment in a peaceful Raised Ranch! Your Martha’s Vineyard sanctuary. Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proximity. 8 minutes away from ferry. Great for family vacation, Island explorations, work trips, hosting wedding guests, wellness retreat, or just a simple gateway, this home will compliment your Martha’s Vineyard experience.

Popular amenities for house rentals in Chilmark

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The charming exterior of the newly renovated home is highlighted by a sloping roof and a welcoming front door. Framing the entrance are neatly trimmed bushes and a small pathway leading to the door. A garage is located on the side, complemented by grassy green surroundings.

5 out of 5 average rating, 23 reviews

Home in Falmouth ~ 5 min drive to beach

Superhost

An indoor pool area features large windows and skylights that allow ample natural light. A tropical plant in a pot is positioned in the foreground. The pool is surrounded by a spacious deck with seating options, providing a relaxed environment for enjoyment.

Home in New Bedford

4.72 out of 5 average rating, 213 reviews

Poseidon's Palace - 2.0

4.93 out of 5 average rating, 55 reviews

A spacious colonial house is framed by lush green grass and mature trees. The exterior features dark shingles with multiple windows reflecting natural light. A winding driveway leads to the entrance, while a wooden fence provides privacy at the rear.

Home in Edgartown

Beautiful Edgartown 3500 sq ft home, heated pool

A fenced backyard with a sparkling pool is surrounded by a manicured lawn and blooming shrubbery. Lounge chairs are positioned near the water, inviting relaxation. The home features a two-story design, with windows overlooking the outdoor space and wooded area in the background.

4.82 out of 5 average rating, 11 reviews

Overlook Poolside Getaway Heated Pool (May - Oct 2

5 out of 5 average rating, 13 reviews

An aerial view showcases a spacious outdoor area highlighted by a heated pool, surrounded by a patio with lounge chairs and green umbrellas. An outdoor dining table, accommodating up to 14 people, is positioned nearby, surrounded by lush landscaping and comfortable seating areas.

Home in Barnstable

Luxury Historic Estate with Expansive Grounds

4.95 out of 5 average rating, 131 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

5 out of 5 average rating, 16 reviews

A serene backyard features a heated pool surrounded by paved stone decking. Multiple lounge chairs are positioned for comfort, offering views of the lush greenery. The two-story home is visible in the background, with a deck equipped for outdoor relaxation.

Home in New Seabury

New Seabury Oasis with Pool!

4.9 out of 5 average rating, 111 reviews

Home in Somerset

Pool + Hot Tub | Sleeps 12 Retreat

Weekly house rentals

The exterior of a two-story wooden home is showcased, featuring a spacious front porch adorned with colorful seating. The surrounding yard is grassy with trees providing shade, and the house is positioned under a clear blue sky, creating a serene environment.

5 out of 5 average rating, 7 reviews

Modern cabin in the woods.

5 out of 5 average rating, 25 reviews

A charming two-story house is depicted, featuring a light exterior with blue accents. A spacious front deck is shown, equipped with white railings and steps leading to a landscaped area. The surrounding greenery offers a serene environment, complementing the welcoming appearance of the home.

Home in Mashpee

Bayview on Seconsett Island

4.91 out of 5 average rating, 95 reviews

A wooden boardwalk leads toward a sandy beach, flanked by tall grasses and plants. The calm ocean stretches out to the horizon, reflecting soft pastel colors of the sky as the sun sets, creating a serene coastal scene.

Home in Sandwich

Cozy Cape Escape with Private Beach!

5 out of 5 average rating, 23 reviews

A charming house is surrounded by lush greenery, featuring a pathway of stone leading to the entrance. Solar panels are mounted on the roof, and large windows allow natural light to fill the space. A small decorative birdbath is visible in the garden area.

Home in Mashpee

Swan nest escape

4.86 out of 5 average rating, 36 reviews

A spacious two-story house is set on a large lawn surrounded by neatly trimmed landscaping. The wraparound porch features white railings and rocking chairs, with a blue door adding a touch of color. Adjacent, a garage is visible, completing the inviting entrance.

Home in Edgartown

Classic Edgartown Stunner close to Town and Beach

A charming Cape Cod home features a well-maintained exterior with a light yellow facade and a steeply pitched roof. Lush green grass surrounds the gravel driveway, and trees provide natural landscaping. A garage is visible on the left side, and a welcoming front entrance is framed by neatly trimmed shrubs.

4.94 out of 5 average rating, 49 reviews

The Perfect Cape Cod Family Getaway-Ideal Location

5 out of 5 average rating, 10 reviews

A modern living space is showcased with a light color palette. A gray sofa and blue armchair are arranged around a round coffee table on a textured area rug. A kitchen area with a central island is visible in the background, along with sliding glass doors leading to a deck.

Home in Tisbury

Entire home newly renovated in August 2025

4.95 out of 5 average rating, 20 reviews

True Cape Cottage! 10 minutes away from beach.

Private house rentals

5 out of 5 average rating, 60 reviews

A serene bay scene is captured at dawn, showcasing calm waters reflecting pastel hues of the sky. Several boats rest gently at a wooden dock, surrounded by a tranquil landscape of trees and misty horizons.

Home in Dartmouth

Mermaid’s Lair. Padanaram Village, So. Dartmouth

5 out of 5 average rating, 19 reviews

Most Chic Spot: Your Martha's Vineyard Getaway!

The exterior of a traditional Cape Cod home is shown at dusk, featuring large windows that illuminate the cozy living area. Adirondack chairs are positioned on the green lawn, surrounded by bare trees. A separate structure is visible, adding to the charm of the backyard.

4.98 out of 5 average rating, 45 reviews

Falmouth Summer Fun–Game Barn-Dog Friendly!

4.96 out of 5 average rating, 26 reviews

Home in Mattapoisett

Buzzard Bay Beachfront Getaway

4.91 out of 5 average rating, 69 reviews

A charming white house is set against a clear blue sky. Lush greenery surrounds the property, with a gravel driveway leading to the attached garage. The front yard features well-maintained shrubs, and the roof is adorned with simple, traditional architecture.

Home in New Seabury

"Summer Escape" at South Cape Beach Estates.

4.93 out of 5 average rating, 71 reviews

A charming house is set amidst lush greenery, featuring a welcoming porch with multiple chairs. Colorful flowers are prominently arranged in the foreground, enhancing the natural surroundings. The structure boasts a traditional design with a sloped roof and large windows, set against a clear blue sky.

Home in Tisbury

Full 3 bedroom House in Tisbury Woods - Sleeps 8

5 out of 5 average rating, 17 reviews

A charming cottage, framed by lush green trees and a well-maintained lawn, stands under a clear blue sky. The exterior features a classic design with a light-colored facade and large windows, offering a glimpse of the sunroom. Surrounding landscaped areas provide a serene and welcoming environment.

Home in Little Compton

Period Cottage Minutes To Ocean