Become a host

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 3,617 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.

1 of 1 pages1 / 1
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.

WalkabilityOutdoor spacesLocation

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.

WalkabilityPetsHeating

4.98 out of 5 average rating, 105 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

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.

WalkabilityOutdoor spacesAmenities

4.98 out of 5 average rating, 52 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

WalkabilityPetsWifi

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!

PetsWalkabilityAir conditioning

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.

PetsWalkabilityGetting around

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 spacesAir conditioning

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.

Outdoor spacesWalkabilityView

4.96 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!

WalkabilityPetsCheck-in

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

PetsWalkabilityAccess

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.

PetsWalkabilityCleanliness

4.99 out of 5 average rating, 120 reviews
Top guest favorite
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 Marstons Mills

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!

WalkabilityOutdoor spacesLaundry

5.0 out of 5 average rating, 233 reviews

Popular amenities for Chilmark pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favorite
Home in Buzzards Bay

Oceanfront | Firepit | Gameroom | Pets | Kayaks

WalkabilityPetsCleanliness

4.98 out of 5 average rating, 123 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

WalkabilityPetsComfort

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

PetsWalkabilityLayout

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 spacesIndoor spaces

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

WalkabilityPetsParking

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

PetsWalkabilityLayout

5.0 out of 5 average rating, 31 reviews
Guest favorite
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

PetsOutdoor spacesComfort

4.83 out of 5 average rating, 18 reviews
Superhost
The charming Cape Cod-style home is framed by lush greenery and a well-kept yard. A welcoming red staircase leads to the front door, while gravel paths and decorative stones outline the landscape, inviting guests to explore the outdoor space.
Home in Oak Bluffs

Oak Bluffs 4BR • 5 Min Drive to Downtown

Outdoor spacesPetsCheck-in

4.88 out of 5 average rating, 76 reviews

Pet-friendly home rentals with a pool

Superhost
Home in Somerset

Fall and Holidays, Entire Home w/ Jacuzzi PETS

Outdoor spacesWalkabilityView

4.88 out of 5 average rating, 129 reviews
Guest favorite
A lagoon-style pool surrounded by a concrete deck provides lounge chairs and shaded areas under umbrellas. A gazebo is visible in the background, complementing the lush greenery that borders the property.
Villa in Wareham

Perfect Farmhouse Discounted for Draft Day!

PetsWalkabilityHospitality

4.89 out of 5 average rating, 101 reviews
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

PetsOutdoor spacesWifi

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 spacesLayout

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 spacesWalkabilityComfort

4.97 out of 5 average rating, 32 reviews
Superhost
Home in Barnstable

Private Saltwater Pool, Game Room, near Beaches!

PetsOutdoor spacesAccess

4.82 out of 5 average rating, 11 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

Outdoor spacesPetsCleanliness

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

Pool Escape in East Falmouth

PetsAccuracyBackyard

4.86 out of 5 average rating, 7 reviews

Private, pet-friendly home rentals

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

PetsWalkabilityAccess

5.0 out of 5 average rating, 45 reviews
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

PetsWalkabilityDecor

5.0 out of 5 average rating, 35 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 spacesHospitality

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

PetsOutdoor spacesEV charging

4.65 out of 5 average rating, 40 reviews
Top guest favorite
Cottage in Falmouth

Saltwind Cottage | Fireplace • Beach • Cozy

WalkabilityOutdoor spacesBeach

5.0 out of 5 average rating, 62 reviews
Guest favorite
Home in West Falmouth

Storybook Cottage, Shining Sea Bikeway, Dogs okay!

WalkabilityDecorBathroom

4.91 out of 5 average rating, 11 reviews
Guest favorite
Home in Bourne

Scraggy Neck 5-Bed Retreat, Fenced Yard with Deck

WalkabilityPetsAmenities

4.96 out of 5 average rating, 25 reviews
Superhost
Home in Edgartown

Edgartown Cottage By The Pond

Outdoor spacesPetsBathroom

4.91 out of 5 average rating, 64 reviews

When is the best time to visit Chilmark?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 12,775 ZARR 12,775 ZARR 10,835 ZARR 10,835 ZARR 7,136 ZARR 7,810 ZARR 10,687 ZARR 12,331 ZARR 8,879 ZARR 8,879 ZARR 29,595 ZARR 10,835 ZAR
Avg. temp-2°C-1°C3°C8°C13°C18°C21°C21°C17°C11°C6°C1°C

Destinations to explore