Pet-friendly holiday rentals in Dukes County

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.

PetsWalkabilityNearby

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 spacesPetsComfort

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.

4.92 out of 5 average rating, 213 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

PetsWalkabilityComfort

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

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!

WalkabilityPetsAmenities

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.

4.96 out of 5 average rating, 140 reviews

**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 spacesWalkabilityWifi

4.86 out of 5 average rating, 108 reviews

An outdoor seating area features two wooden chairs arranged on a patterned rug. Vibrant orange flowers bloom nearby, and a selection of potted plants adds greenery. A private entrance to the guest house is visible, along with gravel and grass areas creating a welcoming atmosphere.

Guest house in Falmouth

Spacious Guest House in Falmouth Village

This spacious studio guest house is tucked away behind a historic sea captain's house. It has a cathedral ceiling, a private entrance, outdoor seating, central AC, eat-in kitchen, wifi, and premium cable television. A great spot for a vacation, this is a place to relax, to walk to the Village with all its restaurants and cafes, walk or bike to the beach (Surf Drive Beach is the closest), and to beautiful nature areas. Outside areas may occasionally be shared with other guests.

PetsWalkabilityTV

4.98 out of 5 average rating, 84 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

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

PetsOutdoor spacesHospitality

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.

WalkabilityPetsValue

5.0 out of 5 average rating, 29 reviews

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

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

WalkabilityOutdoor spacesBeach

Cottage in Chappaquiddick

A bright living space features white walls and a wooden ceiling with ample natural light. A round coffee table is centered in the room, surrounded by a sofa and wicker chairs. A side table holds a lamp, and a colorful artwork is displayed on the wall, with ocean views visible through windows.

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

Outdoor spacesWalkabilityFamily

5.0 out of 5 average rating, 17 reviews