Pet-friendly vacation rentals in Chincoteague

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. • Pets are welcome • Escape the noise, reset in nature •.Epic stargazing • Peaceful sleep • Thoughtful interior design • Large full bath • Comfy patio for coffee, wine, reading • Firepit with wood onsite • Large private outdoor shower in woods • Wide open spaces • Fast WIFI • Superhost 12+ years

Central Location~Walk 2 Dining! Beach Pass & Gear!

You'll Experience the ultimate in coastal living at your beautifully renovated vacation home, a stone's throw from the Beach road. This is your perfect getaway destination. You'll enjoy a bright chef's kitchen with granite countertops and a tiled backsplash, open-concept first floor with cozy living room, and a convenient half bath. Retire to the second level where 2 bedrooms await, including a primary suite with a private bath & private balcony for sipping your coffee & serene morning views 🌄

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!

Rest A'Shored charming Chincoteague getaway

Spacious open floor plan great for entertaining family and friends with all the modern amenities you need! Eat inside at the large dining room table or enjoy the cool evening breeze outside on the fully screened in porch. 3 bedrooms and 2 full baths can comfortably accommodate 2 families with children or 3 couples. Located on Willow street, you are just a short walk to the Chincoteague carnival grounds and Main Street. We are dog friendly as we know they are really part of the family!

"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!

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

"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.

Levin's Waterfront Paradise @ Blackwater Refuge

Levin's paradise is a private and quiet campsite with gorgeous sunsets over Blackwater Wildlife Refuge! Wildlife abounds around the woodlands and marshlands that surround you in this secluded haven! The perfect place to rest and relax by the fire! You will find yourself a world away from it all, yet close to all of the wonderful attractions and dining that Cambridge has to offer! Bring your tent or camper (16 ft or less) and get off the grid! No electric hook up!

Rumbley Cottage on the Tangier Sound-Private Beach

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.

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.

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.

Waterfront FamilyFriendly Home Improved for 2023

NEW IMPROVEMENTS for. 2023! Nautically furnished home on the water and a cul-de-sac which offers a relaxing and safe getaway space for guests. Large windows along the waterside provide for views from most rooms in the house. Watch the boats come and go from Smith Point Marina, or charter a boat for cruising or fishing.