
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 3,543 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.

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.
4.96 out of 5 average rating, 123 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.
4.98 out of 5 average rating, 104 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.
4.98 out of 5 average rating, 50 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.
4.85 out of 5 average rating, 73 reviews
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
4.92 out of 5 average rating, 212 reviews
Quiet & Serene in Aquinnah
Fall asleep to the sounds of the waves. Unique 1000 sqft. 1st floor suite, surrounded by conservation lands and adjacent to the new 320 acre Squibnocket Pond Reservation. The suite consists of 2 elegantly furnished bedrooms and a large marble bathroom. Three sets of French doors open onto an expansive terrace with gardens. Larger bedroom has a beach stone fireplace with a wood stove. 12 minute walk to private beach. Owner occupied on 2nd floor. Charming and serene. Pet Friendly
4.63 out of 5 average rating, 38 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.
4.98 out of 5 average rating, 94 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.
5.0 out of 5 average rating, 170 reviews
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.
4.96 out of 5 average rating, 109 reviews
Charming W. Tisbury Studio Guest Cottage
Charming rustic studio guest cottage with a private yard and outdoor shower, a perfect getaway. Walking distance to North Tisbury Farm and Market and State Road Restaurant and short ride to the small town of West Tisbury where you can check out Alley’s general store or get a great sandwich at 7a’s takeout. Ten minutes to Vineyard Haven and centrally located to all island destinations and many of the scenic Vineyard hiking trails.
5.0 out of 5 average rating, 43 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.
4.85 out of 5 average rating, 20 reviews
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.
4.93 out of 5 average rating, 123 reviewsPopular amenities for Chilmark pet-friendly home rentals
Pet-friendly house rentals

Cape Cod Cotuit Cottage, 3 Bed Near Beaches
5.0 out of 5 average rating, 231 reviews
Waterview, Private, Walk to Beach, Mile to Town
4.83 out of 5 average rating, 217 reviews
Sunset Cove Beach
4.99 out of 5 average rating, 117 reviews
Pinkletink Plantation
4.97 out of 5 average rating, 61 reviews
Oak Bluffs 4BR • 5 Min Drive to Downtown
4.87 out of 5 average rating, 71 reviews
Secluded Aquinnah Cottage
4.83 out of 5 average rating, 18 reviews
Martha's Vineyard Cottage: Walk to Town and Beach
5.0 out of 5 average rating, 28 reviews
NEW! Charming Oak Bluffs Cottage w/ AC - Sleeps 8
4.71 out of 5 average rating, 7 reviewsPet-friendly home rentals with a pool

ShoestringBayHouse, waterfront & pool in Cotuit
4.97 out of 5 average rating, 29 reviews
Poseidon's Palace - 2.0
4.73 out of 5 average rating, 228 reviews
Coastal Charm New Seabury: 5BRs with Private Pool
4.94 out of 5 average rating, 51 reviews
Private pool, hot tub, minutes from beach!
4.5 out of 5 average rating, 10 reviews
Perfect Farmhouse Discounted for Draft Day!
4.89 out of 5 average rating, 100 reviews
Pool Escape in East Falmouth
4.83 out of 5 average rating, 6 reviews
New Seabury Oasis with Pool!
5.0 out of 5 average rating, 21 reviews
Family + Dog Retreat | Fenced Yard + Pool + Beach
4.95 out of 5 average rating, 80 reviewsPrivate, pet-friendly home rentals

Beachfront Cottage w. Yard + Town Access
5.0 out of 5 average rating, 16 reviews
50s Cottage on Martha’s Vineyard w/Private beach
4.61 out of 5 average rating, 61 reviews
Charming Cottage
4.9 out of 5 average rating, 39 reviews
Edgartown Cottage By The Pond
4.9 out of 5 average rating, 62 reviews
Beautiful Martha's Vineyard Home
5.0 out of 5 average rating, 22 reviews
Scraggy Neck 5-Bed Retreat, Fenced Yard with Deck
4.95 out of 5 average rating, 22 reviews
Little Compton's South Shore Serenity
4.96 out of 5 average rating, 68 reviews
All-New, Large Cape w/ Water Views. Walk to Beach.
4.97 out of 5 average rating, 66 reviewsWhen is the best time to visit Chilmark?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 12,515 ZAR | R 12,515 ZAR | R 10,614 ZAR | R 10,614 ZAR | R 6,990 ZAR | R 7,651 ZAR | R 10,469 ZAR | R 12,080 ZAR | R 8,698 ZAR | R 8,698 ZAR | R 28,992 ZAR | R 10,614 ZAR |
| Avg. temp | -2°C | -1°C | 3°C | 8°C | 13°C | 18°C | 21°C | 21°C | 17°C | 11°C | 6°C | 1°C |
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