Pet-friendly vacation rentals in Assateague Island

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a cozy tiny home on a 50-acre farm, surrounded by fields, woods, marsh, and a creek. Curated with hygge comfort and efficiency, you'll love the natural light and calm decor. • Escape the noise & reset in nature • Peaceful sleeping • Thoughtful interior design • Large full bath • Comfy patio for coffee, cocktails, and epic stargazing • Firepit with wood provided • Large private outdoor shower surrounded by woods • Wide open spaces • Fast WIFI • Superhost for 10+ years

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Stunning waterfront panoramic view getaway house

Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself in jaw-dropping panoramic canal views of the Chincoteague Bay. Secluded escape for the nature enthusiast, balanced with country club amenities. Pools, boating and a golf course are within walking distance. Outdoor adventures and pristine beaches are just a short drive away! This property was designed to gather, recharge, explore, love, work remotely and inspire.

Tree Top Loft

Studio apartment is located on a wooded lot in a quiet neighborhood within 4 miles of Salisbury University & Downtown! Off street parking at entrance patio & a flight of stairs leads up to the apartment, which includes a queen size bed, full kitchen with full size refrigerator, 4 burner electric stove, full size washer and dryer. Bathroom includes shower, toilet and vanity, perfect for a week or weekend stay! We are located near Ocean City, Maryland, Assateague National Seashore.

Rumbley Cottage on the Tangier Sound-Private Beach

LAST MINUTE OPENING-09-27 to 10-03-25 !!!! 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. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

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.

Beautiful Waterfront Home-Private, Clean, Relaxing

A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* from Memorial Day to Labor Day.

Bayfront Cottage w/ Amazing Views

Whether you’re enjoying time by the firepit or sipping coffee on the couch, the views of Sinepuxent Bay and Assateague Island make this cottage the ideal spot for your next vacation. The cottage is located in a quiet neighborhood and is only a short drive from Assateague Island, the historic town of Berlin, and the Ocean City Boardwalk.