Pet-friendly holiday rentals in Assateague Island

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Top-rated pet-friendly home rentals in Assateague Island

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Top guest favourite

Guest suite in Ocean Pines

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

PetsOutdoor spacesAir conditioning

4.95 out of 5 average rating, 424 reviews

Top guest favourite

A cozy living area features a light gray sofa adorned with decorative pillows and a small blue ottoman. Natural light brightens the space, showcasing art on the walls and a dining area in the background, complemented by a wooden table and chairs.

Home in Ocean Pines

Home Away from Home , Pet friendly retreat

Welcome to Ocean Pines Getaway, Enter home through a beautiful covered porch with swing for two and lovely seating area. This sweet home has 3 bedrooms & 2 full baths. A fully stocked kitchen , with eat in breakfast nook, Also proper dining room plenty of seating for family Cozy living room with working fireplace. All season sunroom plenty of seating, pub table & bar. Doggie door in sunroom large enough for 100 lb dog, leads to fenced in backyard. $100 pet fee and $125 linens & bath towels.

PetsWalkabilityTV

4.87 out of 5 average rating, 108 reviews

Top guest favourite

Villa in Ocean City

Walk to the Beach! PingPong-Fenced Yard-N64-Bikes!

Escape to the Blue House, a pet-friendly retreat just 6-mins to the beach. - Full kitchen and charcoal grill - Coffee bar (k-cups, espresso, coffee grinder, french press, and pour over) - Fully fenced patio with a fire pit and ping pong - Outdoor shower - 5 Bikes - Northside Park - 2 min walk away - N64 - 48W EV charger - Record player - Pet ramp Sleep 10 (8 Adults 2 Children) in our 3 bedrooms - 1 king, 1 queen, 1 full over full bunk bed, and full sofa bed. NOT POSTED ON C.LIST

WalkabilityOutdoor spacesLayout

4.99 out of 5 average rating, 101 reviews

Top guest favourite

A two-story waterfront home is visible, elevated on stilts with a spacious deck featuring steps leading down to a private dock. Brightly colored kayaks are stored on the dock, and lush trees surround the property, providing a natural, serene backdrop.

Home in Chincoteague

Jay's Retreat: dock, kayaks, EV charger, bikes

Welcome to Jay’s Retreat, a charming waterfront oasis nestled in scenic Oyster Bay. This beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood. End your days by the fire pit, soaking in the peaceful bay views and coastal breeze.

PetsOutdoor spacesBathroom

4.97 out of 5 average rating, 101 reviews

Guest favourite

A waterfront backyard features sandy areas lined with a white picket fence. A picnic table is positioned on the beach, facing the calm waterway. Houses are visible along the banks, framed by trees and distant structures under a soft evening sky.

Home in Ocean Pines

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

WalkabilityPetsSleep quality

4.92 out of 5 average rating, 213 reviews

Top guest favourite

A cozy guest suite is presented, featuring a spacious bed covered with a vibrant blue blanket. Decorative elements include a light-colored rug and a plant next to the bed. A small bookshelf and artwork adorn the walls, contributing to the room's inviting decor.

Guest suite in Fenwick Island

Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!

Unwind and chill in this boho coastal inspired guest suite on the ocean side. At Sea Dunes' private guest king suite, the surf and sand are steps away. Get ready to pack your cooler and enjoy a day in the sun on this beautiful, private dog-friendly beach. Sea Dunes is located in Fenwick Island, DE and nestled between protected state nature parks. Just a short trip in the car to a marina with watersports, kayak adventures on the bay, local dining, farm markets and shopping.

WalkabilityPetsAccess

4.83 out of 5 average rating, 138 reviews

Top guest favourite

A spacious houseboat is docked securely along the water's edge, featuring large windows and a deck area. The surroundings include trees and a sandy space, creating a coastal atmosphere. The sky displays soft clouds illuminated by the setting sun.

Houseboat in Snow Hill

"Jolly"- Houseboat Getaway

"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

PetsOutdoor spacesKitchen

4.88 out of 5 average rating, 186 reviews

Guest favourite

A cozy seating area features a light-colored couch adorned with decorative pillows. A woven coffee table rests on a natural fiber rug, while a window nook is lined with plants, allowing natural light to brighten the space. Wooden accents add a warm touch.

Tiny home in Salisbury

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

PetsOutdoor spacesLong stay

4.84 out of 5 average rating, 251 reviews

Top guest favourite

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

September 12-16 available. Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

WalkabilityOutdoor spacesKitchen

4.99 out of 5 average rating, 266 reviews

Top guest favourite

A comfortable living area features a spacious sectional sofa with decorative pillows, paired with two accent chairs. Light-colored walls and carpeting create a neutral backdrop, while a television rests on a wooden stand opposite the seating. Natural light is offered through nearby windows.

Guest house in Pocomoke City

2 Bedroom Apartment

Centrally located between Chincoteague Island and Ocean City, MD. This pet friendly two bedroom apartment which offers laundry and a spacious kitchen is only steps away from Shad Landing state park and Public Landing. This ground level guesthouse apartment is located 200 feet from our main house is on an over 12 acre partially wooded parcel. Plenty of privacy and room for boat trailer parking.

Outdoor spacesPetsValue

4.94 out of 5 average rating, 193 reviews

Guest favourite

A serene canal view captures waterfront homes reflecting in calm waters at sunset. Docked boats and lush trees frame the scene, showcasing the tranquil atmosphere of the eastern shore. The clear sky hints at the day's end, lending a peaceful ambiance to the surroundings.

Home in Greenbackville

Bayfront Modern Retreat • Dock, Kayaks, Views

Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginia’s Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.

Outdoor spacesWalkabilityKitchen

4.91 out of 5 average rating, 135 reviews

Guest favourite

A tranquil pond is framed by natural stone, featuring a gentle waterfall surrounded by lush greenery. Bright flowering plants and a manicured lawn lead to a serene outdoor seating area overlooking the water, offering a peaceful retreat in nature.

Home in Salisbury

Highbanks House

Forget your worries in this spacious and serene space. Welcome to your dream home! This stunning 5-bedroom, 3-full-bath rancher is nestled on over 6 acres of private land, offering a perfect blend of comfort and nature. Located just 6 miles from downtown Salisbury and 8 miles from Salisbury University, this property provides both tranquility and convenience.

WalkabilityPetsGetting around

4.83 out of 5 average rating, 181 reviews