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Pet-friendly vacation rentals in Chilmark

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in Chilmark

  • Total vacation rentals

    Explore 80 vacation rentals in Chilmark

  • Nightly prices starting at

    Chilmark vacation rentals start at R 3,559 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Chilmark vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chilmark rentals

  • 4.9 Average rating

    Chilmark stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Chilmark

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
Home in West Tisbury

Lambert's Cove, Water view, Beach pass

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.

Outdoor spacesWalkabilityAccess

4.96 out of 5 average rating, 123 reviews
Top guest favorite
Home in Oak Bluffs

Arrowsmith Cottage-Oak Bluffs Near Eastville Beach

Welcome to Arrowsmith Cottage! If you are considering bringing your small dog, please first contact me (scroll down on the cottage's listing page and click on the "Contact Host" button), and tell me a little bit about him/her, as dogs require homeowner's written approval and guest’s agreement to the pet fee and homeowners’ pet rules. We cannot allow cats, birds, or any animals other than one pre-approved dog. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.

PetsWalkabilityLayout

4.98 out of 5 average rating, 105 reviews
Guest favorite
A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.
Home in Oak Bluffs

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Outdoor spacesPetsAccuracy

4.92 out of 5 average rating, 213 reviews
Guest favorite
A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.
Home in Oak Bluffs

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Outdoor spacesPetsTV

4.83 out of 5 average rating, 219 reviews
Guest favorite
An open living area features a light-colored sofa adorned with blue and white cushions. A flat-screen TV is mounted above a white brick fireplace. Large windows provide natural light, and a dining area with a table and chairs is visible in the background.
Home in Oak Bluffs

**Vineyard Vacation Retreat** -3 BR

Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. 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.

Outdoor spacesWalkabilityBathroom

4.96 out of 5 average rating, 140 reviews
Top guest favorite
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.

PetsOutdoor spacesBiking

5.0 out of 5 average rating, 172 reviews
Top guest favorite
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.
Home in West Tisbury

Lambert's Cove Oceanview Beach Pass Trails nearby

Traditional 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 , a 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. Beach towels along with4 beach chairs provided.

PetsWalkabilitySleep quality

4.96 out of 5 average rating, 109 reviews
Guest favorite
A charming Cape-style house features a welcoming front porch with decorative railings and two red doors. Lush greenery and colorful flower beds surround the home, while a pebble driveway leads to the entrance. The exterior is complemented by a clear blue sky.
Home in Edgartown

The Seashell Cove - Martha's Vineyard

Nestled in the exclusive Katama neighborhood of Edgartown, this sunny Cape retreat is perfect for families or friends. Just two miles from South Beach, it offers cozy interiors, high-speed Wi-Fi, and smart TVs. Outdoors, enjoy a farmer's porch, deck with a direct gas-line grill, and spacious yards. Close to downtown Edgartown, bike paths, and attractions like the Chappaquiddick ferry, this property is ideal for both summer adventures and peaceful off-season stays.

WalkabilityPetsKitchen

4.94 out of 5 average rating, 109 reviews
Top guest favorite
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.
Guest suite in West Falmouth

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!

PetsOutdoor spacesComfort

5.0 out of 5 average rating, 244 reviews
Top guest favorite
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.
Cottage in Tisbury

Not Your Great Aunt's Island Cottage

In the heart Vineyard, 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 • Easily walkable 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

Outdoor spacesWalkabilityGetting around

4.96 out of 5 average rating, 320 reviews
Top guest favorite
A serene sunset over a calm body of water reflects vibrant orange and soft blue hues. Lush green grass borders the shore, while silhouettes of distant trees frame the scene. A dock is visible on the left, offering a peaceful spot to enjoy the view.
Home in Wareham

Sunset Cove Beach

This ocean view cottage is perfect for you and your family to relax, unwind and adore the wonderful scenery it has to offer. This charming cottage is on a quiet dead-end street, suitable for a small family or a couple, seeking to appreciate the neighborhood and beaches without the hassle of cape traffic. Come and enjoy the warm water, beautiful sunrises, breathtaking sunsets, and much more.

WalkabilityOutdoor spacesGrill

4.99 out of 5 average rating, 120 reviews
Guest favorite
A historic lighthouse stands beside a renovated white keepers home, both set on a lush green lawn. The Atlantic Ocean stretches out in the background under clear blue skies, offering a serene coastal view.
Lighthouse in Pocasset

Wings Neck Lighthouse

Once in a lifetime experience to stay in a Lighthouse. Historic, unique and charming but with all of the conveniences that make a great vacation. Just feet from the Atlantic with 360 degrees of ocean view. Beautiful, peaceful and memorable all year long. Sandy private association beach just steps away. Expansive lawn and patio for enjoying salt air, waves, boats and sunsets.

Outdoor spacesPetsQuiet

4.94 out of 5 average rating, 126 reviews

Popular amenities for Chilmark pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favorite
A three-story house is nestled within a lush green yard, showcasing two expansive outdoor decks adorned with comfortable seating. Sunlight filters through trees, creating a serene atmosphere. The lower level features walk-out access, enhancing the connection to the outdoor space surrounded by natural landscaping.
Home in Tisbury

Sunny, Spacious Vineyard Retreat

Outdoor spacesPetsSleep quality

4.97 out of 5 average rating, 308 reviews
Top guest favorite
Home in Buzzards Bay

Oceanfront | Firepit | Gameroom | Pets | Kayaks

Outdoor spacesPetsAmenities

4.98 out of 5 average rating, 123 reviews
Top guest favorite
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

PetsWalkabilityLaundry

4.98 out of 5 average rating, 52 reviews
Superhost
A cozy living area showcases a large, comfortable sofa and a wooden coffee table, with a mounted map adding character to the space. Sunlight streams through multiple windows, illuminating the room's airy feel. A dining table is visible, suggesting a welcoming atmosphere for gatherings.
Home in Chilmark

Evelyn's Menemsha Camp - Best Vineyard View

WalkabilityOutdoor spacesGetting around

4.86 out of 5 average rating, 21 reviews
Superhost
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.
Home in Chilmark

Chilmark Cape in private wooded setting

WalkabilityPetsGrill

4.85 out of 5 average rating, 74 reviews
Top guest favorite
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

PetsOutdoor spacesBeach

4.98 out of 5 average rating, 95 reviews
Top guest favorite
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.
Home in West Tisbury

Tucked away Up Island

Outdoor spacesWalkabilityAccuracy

4.98 out of 5 average rating, 50 reviews
Top guest favorite
A charming two-story cottage features a shingled exterior with a pitched roof. The inviting front porch is supported by wooden pillars and surrounded by lush greenery. A white picket fence encloses the well-kept lawn, creating a warm curbside appeal.
Home in Edgartown

Martha's Vineyard Cottage: Walk to Town and Beach

PetsOutdoor spacesDecor

5.0 out of 5 average rating, 29 reviews

Pet-friendly home rentals with a pool

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

Poseidon's Palace - 2.0

WalkabilityPetsLayout

4.74 out of 5 average rating, 232 reviews
Guest favorite
An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.
Home in New Seabury

Coastal Charm New Seabury: 5BRs with Private Pool

WalkabilityOutdoor spacesCondition

4.94 out of 5 average rating, 53 reviews
Top guest favorite
An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.
Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

Outdoor spacesPetsView

4.97 out of 5 average rating, 32 reviews
Top guest favorite
An aerial view of the historic estate is displayed, showcasing the expansive lawn and vibrant greenery surrounding the home. The private pool area is visible in the backyard, alongside the well-maintained grounds. The house features inviting wraparound porches and ample outdoor space.
Home in Cataumet

1.2 Acre Estate | Pool | Close to Beaches | Games

PetsWalkabilitySleep quality

5.0 out of 5 average rating, 31 reviews
Guest favorite
Home in Falmouth

Pool Escape in East Falmouth

PetsNearbyCleanliness

4.86 out of 5 average rating, 7 reviews
Superhost
Home in Barnstable

Private Saltwater Pool, Game Room, near Beaches!

PetsOutdoor spacesParking

4.82 out of 5 average rating, 11 reviews
Top guest favorite
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!

PetsWalkabilityKitchen

5.0 out of 5 average rating, 24 reviews
Guest favorite
A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.
Home in East Falmouth

Family + Dog Retreat | Fenced Yard + Pool + Beach

WalkabilityOutdoor spacesAccess

4.95 out of 5 average rating, 84 reviews

Private, pet-friendly home rentals

Top guest favorite
A cozy living area features a lightweight sofa adorned with colorful cushions, complemented by a pink upholstered chair. Large windows reveal ocean views, allowing natural light to fill the space. A small table holds fruit and a book, creating a welcoming setting.
Cottage in Chappaquiddick

Beachfront Cottage + Studio w. Town Access

WalkabilityOutdoor spacesQuiet

5.0 out of 5 average rating, 35 reviews
Guest favorite
A rustic studio cottage is presented with a sloped roof and blue siding. A wooden deck leads to the entrance, flanked by a garden with flower beds. A grill is visible on the deck, and a stone pathway meanders through the green yard.
Guesthouse in West Tisbury

Charming W. Tisbury Studio Guest Cottage

WalkabilityPetsNearby

5.0 out of 5 average rating, 45 reviews
Superhost
A beach cottage showcases a wooden deck leading up to its exterior, featuring multiple windows and a blue trim. Surrounding greenery and sandy terrain create a natural setting. The entrance is visible, alongside a glimpse of parked vehicles in the background.
Cabin in Aquinnah

50s Cottage on Martha’s Vineyard w/Private beach

WalkabilityOutdoor spacesBathroom

4.61 out of 5 average rating, 62 reviews
Superhost
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.
Apartment in Aquinnah

Quiet & Serene in Aquinnah

WalkabilityOutdoor spacesHospitality

4.65 out of 5 average rating, 40 reviews
Superhost
A spacious living area is highlighted by a large blue sectional sofa, complemented by several accent pillows. Large glass doors provide a view of the deck, while pendant lights hang from a vaulted wooden ceiling, enriching the open atmosphere.
Home in Tisbury

Carolyn's Vineyard Haven

PetsWalkabilityFamily

4.68 out of 5 average rating, 214 reviews
Superhost
A wooden arbor frames the pathway leading to the cottage entrance, which is highlighted by a bright yellow door. Soft pink petals cover the ground, creating a charming welcome. Lush greenery surrounds the pathway, adding to the inviting atmosphere of the entryway.
Cottage in Tisbury

Charming Cottage

PetsOutdoor spacesLayout

4.88 out of 5 average rating, 40 reviews
Top guest favorite
Aerial view of a spacious family home set in a tranquil neighborhood. The property features a well-maintained lawn, a circular driveway, and proximity to the water, highlighting nearby homes and scenic views of the bay.
Home in Falmouth

All-New, Large Cape w/ Water Views. Walk to Beach.

WalkabilityOutdoor spacesKitchen

4.97 out of 5 average rating, 69 reviews
Top guest favorite
Home in Oak Bluffs

Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ

WalkabilityOutdoor spacesGrill

4.95 out of 5 average rating, 21 reviews

When is the best time to visit Chilmark?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 12,571 ZARR 12,571 ZARR 10,661 ZARR 10,661 ZARR 7,021 ZARR 7,685 ZARR 10,516 ZARR 12,134 ZARR 8,736 ZARR 8,736 ZARR 29,121 ZARR 10,661 ZAR
Avg. temp-2°C-1°C3°C8°C13°C18°C21°C21°C17°C11°C6°C1°C

Destinations to explore