Pet-friendly holiday rentals in Chilmark

4.96 out of 5 average rating, 123 reviews

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 spacesPetsLaundry

4.98 out of 5 average rating, 105 reviews

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.

Outdoor spacesPetsNearby

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, 51 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.

WalkabilityPetsAir conditioning

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, 74 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.

PetsOutdoor spacesHospitality

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, 95 reviews

Peaceful Retreat Near Up-Island Beaches

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.

WalkabilityOutdoor spacesSleep quality

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.

5.0 out of 5 average rating, 171 reviews

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.

WalkabilityOutdoor spacesGetting around

4.96 out of 5 average rating, 109 reviews

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 spacesPetsDecor

4.94 out of 5 average rating, 109 reviews

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.

Outdoor spacesWalkabilityValue

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.

4.85 out of 5 average rating, 20 reviews

Evelyn's Menemsha Camp - Best Vineyard View

Evelyn's House on the hill overlooking Menemsha Beach is the classic Marthas Vineyard Beach Cottage. Evelyn Flanders built her " Camp"in 1909 where the views of Menemsha Harbor and famous sunsets would be about as good as it gets. It's the same today. With 2 bedrooms, 2 baths and a loft it's perfect beach base camp.. Take the path to Menemsha beach or your passes to Lucy Vincent. You are most welcome to bring one pet.

PetsWalkabilityQuiet

4.96 out of 5 average rating, 320 reviews

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

PetsWalkabilityGetting around

5.0 out of 5 average rating, 233 reviews

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!

PetsWalkabilityNearby

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.

4.97 out of 5 average rating, 167 reviews

Mid-Century Modern home 5 minute walk to beach

Perfect for a family or friend's getaway- relax and unwind in this unique home that feels like a treehouse. Hang out on the fully furnished decks, stargaze on the roof deck, or stroll to Wood Neck beach and explore the marsh. Close to Falmouth restaurants and shopping, Shining Sea Bikeway, and other Cape Cod attractions.

Outdoor spacesWalkabilityValue

Popular amenities for Chilmark pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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.

4.83 out of 5 average rating, 219 reviews

Waterview, Private, Walk to Beach, Mile to Town

PetsOutdoor spacesGetting around

4.99 out of 5 average rating, 120 reviews

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

Outdoor spacesPetsDecor

4.9 out of 5 average rating, 126 reviews

Home in Edgartown

Katama Barn

Outdoor spacesPetsBarbecue

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.

4.88 out of 5 average rating, 75 reviews

Oak Bluffs 4BR • 5 Min Drive to Downtown

WalkabilityPetsFamily

4.95 out of 5 average rating, 21 reviews

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

PetsWalkabilityParking

A charming two-story house is featured, showcasing shingle-style architecture and a welcoming front porch. White pillars support a broad balcony, while large windows allow for natural light. The well-maintained exterior is accented by a well-paved path and surrounding greenery.

4.97 out of 5 average rating, 62 reviews

Pinkletink Plantation

Outdoor spacesWalkabilityParking

4.69 out of 5 average rating, 213 reviews

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

Outdoor spacesWalkabilityLong stay

The exterior of a charming two-story house is viewed from the front, featuring a wrap-around porch adorned with hanging flower baskets. Lush greenery surrounds the entrance, and a clear blue sky looms above, enhancing the welcoming atmosphere of the property.

5.0 out of 5 average rating, 28 reviews

Updated cottage/ ocean views

Outdoor spacesWalkabilityCondition

Pet-friendly home rentals with a pool

4.74 out of 5 average rating, 232 reviews

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

WalkabilityPetsParks

4.97 out of 5 average rating, 32 reviews

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 spacesPetsPool

4.94 out of 5 average rating, 53 reviews

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

Outdoor spacesWalkabilityComfort

4.58 out of 5 average rating, 12 reviews

Home in New Seabury

Private pool, hot tub, minutes from beach!

WalkabilityHospitalityAccuracy

4.86 out of 5 average rating, 7 reviews

Pool Escape in East Falmouth

PetsNearbyFamily

4.86 out of 5 average rating, 51 reviews

Home in Barnstable

Relaxing Cape Home <3mi-beach

PetsWalkabilityPool

5.0 out of 5 average rating, 12 reviews

Tiny home in Sandwich

Cape Cod Resort|Cabin w/Pool & Private Beach

Outdoor spacesWalkabilityComfort

4.92 out of 5 average rating, 50 reviews

A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.

Condo in Tisbury

Private 3bdrm Condo Tashmoo Woods

Outdoor spacesPetsHospitality

Private, pet-friendly home rentals

Guesthouse in West Tisbury

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.

Charming W. Tisbury Studio Guest Cottage

PetsWalkabilityComfort

5.0 out of 5 average rating, 44 reviews

4.65 out of 5 average rating, 40 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.

Apartment in Aquinnah

Quiet & Serene in Aquinnah

PetsWalkabilityQuiet

Cottage in Chappaquiddick

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.

Beachfront Cottage + Studio w. Town Access

PetsOutdoor spacesBeach

5.0 out of 5 average rating, 35 reviews

4.61 out of 5 average rating, 62 reviews

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

PetsOutdoor spacesAccuracy

4.88 out of 5 average rating, 40 reviews

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

PetsWalkabilityFamily

4.93 out of 5 average rating, 27 reviews

Cottage in Oak Bluffs

#Islandbeachrose. Walk To Beach and Town!

Outdoor spacesWalkabilityGetting around

The front porch features a seating area with a plush sofa and a coffee table. A rocking chair is positioned beside the entrance. Potted plants and hanging flower baskets add natural beauty, while an American flag gently moves in the breeze.

5.0 out of 5 average rating, 75 reviews

Beautiful Home in Falmouth Village

Outdoor spacesWalkabilityHiking