Family-friendly holiday rentals 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

4.98 out of 5 average rating, 230 reviews

A bright sleeping area features a spacious white bed with decorative pillows and bedside lamps. A small kitchen area with light-colored cabinetry is visible in the background, complemented by a large window allowing natural light. A cozy seating area adds to the warmth of the space.

Guest house in Chilmark

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom and outdoor shower. A small kitchen features butcher block countertops, stainless steel sink, refrigerator and 2 burner electric stove and island. Air conditioning and heat. The space comes with a walk -on-pass to Lucy Vincent Beach.

4.97 out of 5 average rating, 156 reviews

A charming post and beam house is set back from a sandy driveway, surrounded by lush greenery and colorful flowers. Large windows on the upper level allow for natural light, providing a welcoming entrance to the home.

Home in West Tisbury

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

Guest house in West Tisbury

An open studio layout is showcased, featuring a spacious bed with a metal frame. A cozy seating area is arranged with patterned cushions and a wooden coffee table. Natural light pours in through multiple windows, illuminating the warm wood flooring and inviting ambiance.

4.97 out of 5 average rating, 98 reviews

Vineyard Meadow Artist Studio

This lovely artist's studio is just steps from miles of trails. Walk to the beach or meander through the woods of Long Point Wildlife Refuge, experiencing the serenity of this still untouched corner of Martha's Vineyard. This studio includes a bathroom with a shower, a washer/dryer and a kitchenette. It is the perfect spot for a lone artist, a couple or a family to enjoy Martha's Vineyard any time of year. This property shares the driveway and parking with Vineyard Meadows Writer's Cottage.

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.

4.93 out of 5 average rating, 166 reviews

A spacious living area showcases wooden flooring and high ceilings with exposed beams. Large windows fill the space with natural light, while a cozy sofa and a white coffee table invite relaxation. A kitchen area is visible in the background, providing a functional and open layout.

Home in Vineyard Haven

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

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.

4.97 out of 5 average rating, 268 reviews

A spacious bedroom features a large king bed with a custom wood frame and soft bedding. Natural light enters through two windows with sheer curtains, and a colorful abstract art piece adorns the wall. A full-length mirror stands adjacent to the bed on a textured area rug.

Flat in Falmouth

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

4.83 out of 5 average rating, 241 reviews

The exterior of the cottage is shown, featuring a welcoming blue door and a well-maintained front yard with colorful flowers. The view includes a quiet street lined with trees and nearby houses, providing a glimpse of the neighborhood atmosphere.

Cottage in Fairhaven

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

4.97 out of 5 average rating, 350 reviews

A cozy outdoor seating area is arranged with several white lounge chairs on a gravel surface. A brick fireplace is positioned near the house, accompanied by potted plants and a view of the deck area adorned with covered furniture in the background.

Cottage in West Chop

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

Cottage in Vineyard Haven

The cottage is adorned with warm, glowing string lights that outline the roof and windows, creating a welcoming ambiance. A lush wreath decorates the front door, while charming wood paneling and multiple windows enhance the inviting exterior.

4.96 out of 5 average rating, 295 reviews

Ferry (Car) Reservations Available for Summer 2026

F͟R͟E͟E͟ ͟C͟A͟R͟ ͟F͟E͟R͟R͟Y͟ ͟R͟E͟S͟E͟R͟V͟A͟T͟I͟O͟N͟ ͟F͟O͟R͟ ͟A͟U͟G͟U͟S͟T͟ ͟2͟2͟-͟2͟9͟!͟ In town, 1930's cottage, lovingly updated by architect-owner. • Stylish decor, open floor plan, granite terrace • 2 blocks to Main St/harbor/ferry/town beach/playhouse • Central Air • Close to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

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, 203 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!

Popular amenities for Chilmark family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 35 reviews

A modern kitchen features a spacious island with four bar stools and stylish pendant lighting above. Sleek white cabinetry complements the elegant quartz countertop. Large windows provide natural light, and stainless steel appliances, including a gas range and refrigerator, are visible in the background.

Home in Oak Bluffs

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

Guest suite in West Tisbury

The outdoor deck features two loungers with colorful striped cushions, a small white table, and potted plants. A hot tub is positioned nearby, surrounded by greenery that creates a tranquil setting. The home's windows allow for natural light to enhance the spaces.

4.97 out of 5 average rating, 88 reviews

Quiet West Tisbury 2 BDR Suite

Guest house in Oak Bluffs

Two individuals are positioned in front of lush greenery and blooming yellow flowers. The vibrant colors of the foliage provide a natural backdrop, contributing to a serene atmosphere. Soft light filters through the plants, creating a gentle glow around the subjects.

4.97 out of 5 average rating, 112 reviews

Oak bluffs cottage Perfect place to honeymoon!

4.98 out of 5 average rating, 56 reviews

A modern kitchen is featured with a large island topped with white quartz. Stainless steel appliances are visible, along with an array of utensils. A bright dining area is beyond the kitchen, with sliding glass doors leading to a lush outdoor space. The living area is comfortably arranged with a dark sofa and a TV.

Home in Mashpee Neck

Charming Cape House with Private Hot Tub !

Home in West Hyannis Port

The exterior of the house is surrounded by well-maintained greenery and tall, lush trees. A welcoming front entrance is framed by neatly trimmed hedges, leading to a slate pathway and steps. Large windows allow natural light to brighten the façade.

4.98 out of 5 average rating, 165 reviews

Luxury House 0.25 mi from Craigville Beach

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!

5 out of 5 average rating, 51 reviews

An inviting living room features a light-colored sofa and a natural wood coffee table. Artwork and plants add warmth, while natural light fills the space through ample windows. A large television is mounted on the wall, providing entertainment options for guests.

Home in Edgartown

Valentine's Retreat Hot Tub Fire Pit Trails Beach

4.96 out of 5 average rating, 45 reviews

A spacious dining area features a rustic wooden table surrounded by chairs, accommodating multiple guests. A stylish chandelier hangs overhead, illuminating the space. The adjoining kitchen is visible with modern appliances, and a window allows natural light to fill the room, enhancing the inviting atmosphere.

Home in Teaticket

Newly Renovated Home! Hottub! Walk 2 beach! Slps 9

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 100 reviews

A charming path leads to the entrance of a house, framed by a white picket fence and lush greenery. Flowering plants line the walkway, which is paved with bricks and gravel. Solar panels are visible on the roof, complementing the natural surroundings.

Home in Mashpee Neck

Cozy garden retreat close to it all! Pet friendly

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

4.94 out of 5 average rating, 317 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!

5 out of 5 average rating, 105 reviews

Two black Adirondack chairs are positioned around a small table in a serene backyard setting. A bowl filled with lobster sits atop the table, with a fish pond and rocks in the background, complemented by sun rays filtering through the foliage.

Flat in Sandwich

Cozy Large Private Pet Friendly Studio

Guest house in Vineyard Haven

A charming cottage is surrounded by lush greenery and blooming hydrangeas. A small Weber grill is positioned on the stone patio, and a wooden pathway leads to the covered porch. The facade features multiple screened doors and windows, inviting natural light into the space.

4.85 out of 5 average rating, 275 reviews

Sweet Vineyard Haven Cottage

4.85 out of 5 average rating, 256 reviews

The cottage exterior features a shingle facade with flower boxes adorned with colorful blooms. Two large windows provide natural light, while a wooden step leads to the entrance. The surrounding yard is well-kept, with green grass and vibrant hydrangeas adding to the inviting atmosphere.

Cottage in West Yarmouth

Charming Cottage near Beach and Ferry.

4.91 out of 5 average rating, 134 reviews

A single-story ranch home is set against a clear blue sky, featuring a neatly landscaped front yard with low shrubs and grass. The entrance includes a welcoming front door with decorative trim and steps leading up to it. Mature trees provide shade around the property.

Home in Falmouth

Fiddler's Green - families and pets welcomed!

4.88 out of 5 average rating, 172 reviews

Two wooden adirondack chairs are positioned on a grassy area, facing a tranquil lake surrounded by trees. Bright yellow daffodils bloom nearby, adding a touch of color to the natural landscape under a clear blue sky.

Guest house in Dartmouth

Lovely Lakeside Cottage

Family-friendly home rentals with a pool

4.76 out of 5 average rating, 33 reviews

An inviting outdoor space is depicted, featuring a spacious in-ground pool surrounded by lounge chairs. String lights are strung across the pool area, illuminating the backyard. A pool house and umbrellas provide additional amenities, while the home's facade is visible in the background.

Home in Barnstable

Heated Pool Oasis | 5 Min to Cape Cod Beaches!

5 out of 5 average rating, 7 reviews

A three-story townhome is nestled among lush greenery, showcasing a muted gray exterior. Large windows bring natural light into the living spaces. A patio is visible on the lower level, furnished with outdoor seating, offering a tranquil view of the surrounding landscape.

Townhouse in Oak Bluffs

Oak Bluffs Renovated Retreat

4.94 out of 5 average rating, 107 reviews

A cozy studio space features sloped ceilings and warm wooden flooring. A spacious bed is dressed in white linens, with accent pillows adding a touch of color. A small kitchenette is visible beside a comfortable chair and a blue rug, offering a relaxed atmosphere.

Guest suite in Dartmouth

The Loft @ Beechwood. Private, comfy, coastal!

Holiday home in West Tisbury

A charming Cape-style house with a stone façade is nestled among trees. A well-manicured lawn leads to the front, where several outdoor chairs are positioned for relaxation. Sunlight filters through the surrounding foliage, enhancing the serene outdoor setting.

4.91 out of 5 average rating, 11 reviews

Beautiful Family Friendly House with Pool

4.67 out of 5 average rating, 643 reviews

A sunlit corner of the guesthouse features a dining area with a round table and four wooden chairs, surrounded by large windows that offer views of the ocean. A decorative cabinet and television are positioned nearby, enhancing the inviting space.

Cabin in Falmouth

Waterside Guest House

4.8 out of 5 average rating, 114 reviews

A charming stone exterior features a distinctive arched design, with two red doors providing access to the private studio. Lush greenery surrounds the entrance, complemented by a gravel pathway and neatly trimmed bushes, evoking a sense of tranquility in the outdoor space.

Flat in North Falmouth

Falmouth, Cozy Studio Near Old Silver Beach

Apartment in Vineyard Haven

The exterior of a cozy blue condo is shown, surrounded by green grass and trees. A wooden fence and picnic table are visible in the foreground, as well as a large tree with budding leaves. The building features multiple windows with white shutters.

4.78 out of 5 average rating, 23 reviews

Martha’s Vineyard Condo * Near Ferry