Pet-friendly home rentals near Chincoteague Island

4.99 out of 5 average rating, 148 reviews

Mins to Beach~Walk to Food and Drinks +Beach 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 🌄

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!

4.95 out of 5 average rating, 423 reviews

4.99 out of 5 average rating, 350 reviews

A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.

Farm stay in Onancock

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!

Home in Chincoteague Island

A modern kitchen and dining area feature light-colored cabinetry and stainless steel appliances. A large wooden dining table accommodates eight, surrounded by aqua-colored chairs. Natural light filters through the window, enlivening the space, while a decorative pendant light adds character above the table.

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!

4.92 out of 5 average rating, 221 reviews

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.

4.97 out of 5 average rating, 101 reviews

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.

4.88 out of 5 average rating, 102 reviews

A metal tray filled with freshly steamed crabs sits on a wooden table. The crabs are coated with seasoning and display vibrant orange-red shells. In the background, natural light filters through a screened porch, adding a warm ambiance to the scene.

Home in Onancock

Escape To A “True” Chesapeake Waterfront Property!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Bayview House", an updated 1950's cape cod featuring lots of original features with many modern upgrades. It sits on our 44-acre property along with our "Sunset House" - also available on Airbnb.

4.88 out of 5 average rating, 186 reviews

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!

4.99 out of 5 average rating, 266 reviews

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.

Guesthouse in Pocomoke City

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.

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.

4.94 out of 5 average rating, 193 reviews

4.91 out of 5 average rating, 135 reviews

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.

4.83 out of 5 average rating, 181 reviews

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.

4.95 out of 5 average rating, 195 reviews

Cottage in Chincoteague

Summer's Seaside Cottage | Near Ponies & Beach

Welcome to Summer's Seaside Cottage -- a breezy, costal retreat designed for slow mornings, salty air, and unforgettable island evenings on Chincoteague Island. Whether you're here for the wild ponies, beach days, or simply to unwind, this is the kind of place that instantly feels like a vacation.

Popular amenities for pet-friendly home rentals near Chincoteague Island

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.93 out of 5 average rating, 290 reviews

A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

Home in Ocean City

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

4.9 out of 5 average rating, 145 reviews

A well-appointed bedroom features a wooden bed with soft green linens and decorative pillows. A bedside table with drawers holds a vintage clock and a decorative object. A woven light fixture hangs above, and natural light filters through the window covered by blinds.

Home in Salisbury

Stella

4.97 out of 5 average rating, 109 reviews

The front exterior of a charming two-story house is shown, featuring a pitched roof and light-colored siding. A bright blue door welcomes visitors. A white picket fence encloses the front yard, which is neatly landscaped with greenery and flowering plants.

Home in Ocean City

Dolores by the Sea- Family Groups ONLY

5.0 out of 5 average rating, 17 reviews

Captain's Loft

5.0 out of 5 average rating, 25 reviews

New house, Bay views, 4 Beds, Game room

A hot tub is situated on a wooden deck, bubbles rising gently from the water's surface. The vibrant blue exterior of the house is contrasted by pink trim. Sunlight reflects off the hot tub, creating a bright and inviting ambiance. A screened porch and balcony are visible in the background.

4.98 out of 5 average rating, 57 reviews

Hot Tub. Fire pit. Fenced Yard. Games. Downtown.

5.0 out of 5 average rating, 14 reviews

Sialang - Waterfront, Pier, Hot Tub & Kayaks

A charming coastal home features a light blue front door and large windows adorned with greenery. Stone accents and a gabled roof complement the inviting appearance. A well-maintained lawn with potted plants and garden decorations surrounds the house, enhancing its welcoming atmosphere.

4.98 out of 5 average rating, 84 reviews

cozy sunset cottage

Pet-friendly home rentals with a pool

Farm stay in Princess Anne

A bright living area features wooden beams and large windows adorned with plaid curtains. A variety of cushions decorate a sectional sofa and a leather couch. A television offers a view of a sports event, while an area rug adds pattern to the wooden floor.

Farmhouse located on a horse farm

4.95 out of 5 average rating, 124 reviews

4.98 out of 5 average rating, 222 reviews

Cottage in Berlin

Bayfront Cottage w/ Amazing Views

4.81 out of 5 average rating, 169 reviews

The image captures the exterior of a charming blue house surrounded by vibrant flower beds, primarily featuring red blooms. A yellow sign displaying the house name and address stands prominently in the foreground. Soft evening light enhances the welcoming atmosphere.

Bungalow in Horntown

Nature's retreat @ the Bug-a-Boo. Beaches nearby

4.93 out of 5 average rating, 152 reviews

A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.

Home in Ocean City

3 BR Waterfront Home, Minutes to the Beach

4.99 out of 5 average rating, 140 reviews

A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.

Home in Ocean Pines

Ocean Pines Retreat with Beach Club

4.78 out of 5 average rating, 243 reviews

A private balcony features two turquoise adirondack chairs facing the ocean. The oceanfront view showcases the sandy beach and rolling waves, inviting moments of relaxation and enjoyment. A decorative 'Seaside' sign is displayed on the wall, enhancing the coastal ambiance.

Condo in Ocean City

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

5.0 out of 5 average rating, 123 reviews

The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.

Condo in Ocean City

Beautiful waterview 2B condo w/Dock&Close to Beach

4.83 out of 5 average rating, 109 reviews

A sunny deck features white lounge chairs beside an above-ground pool. Lush greenery lines the background, providing a natural setting. A tall umbrella offers shade, and a potted plant adds a touch of greenery to the space.

Holiday home in Berlin

Berlin Beach House, near Ocean City & Assateague!

Private, pet-friendly home rentals

4.94 out of 5 average rating, 542 reviews

Tiny home in Accomac

Little Red House on a Rural Farm for Stargazing

4.84 out of 5 average rating, 251 reviews

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

4.88 out of 5 average rating, 68 reviews

Aerial view of a peaceful coastal retreat set on a spacious property surrounded by lush greenery and water. A sandy beach extends along the shoreline, complemented by tranquil marshlands and distant woodlands. The house is positioned towards the center, offering a sense of privacy amidst nature.

Cottage in Onancock

Peaceful 5 bedroom cottage on the Eastern Shore...

4.96 out of 5 average rating, 75 reviews

A rustic cabin is surrounded by tall pine trees, featuring a spacious deck with multiple seating areas. An American flag is displayed, while a grill is positioned nearby. Large windows allow natural light into the interior, creating a welcoming exterior view.

Cabin in Onancock

Awesome private off grid Creek front Cabin.

4.91 out of 5 average rating, 46 reviews

Cottage in Melfa

Waterfront 1BR on Working Farm w/ Deck + View

4.81 out of 5 average rating, 42 reviews

Farm stay in Crisfield

Home of The Terrapin King

4.88 out of 5 average rating, 8 reviews

Home in Berlin

That South Point Joint - Assateague/Golf/Boat Ramp

Home in Chincoteague Island

A charming three-story historic home is shown with a well-maintained front yard and neatly trimmed grass. The house features a wraparound porch with large windows, allowing natural light to illuminate the interior. A shed is visible in the backyard, providing additional storage options.

Casa de Isla Welcomes You.

4.63 out of 5 average rating, 84 reviews

Pet-friendly home rentals with a hot tub

4.72 out of 5 average rating, 18 reviews

Home in Onancock

Camp Chesapeake House 6 acre Waterfront Retreat

5.0 out of 5 average rating, 13 reviews

A three-story waterfront home features multiple covered porches with white railings. A brick pathway leads through well-maintained lawns and landscaping with flowers and ornamental grasses, guiding to the main entrance. Soft gray skies and greenery provide a serene backdrop.

Home in Onancock

Harbor Master

4.69 out of 5 average rating, 29 reviews

The exterior of a two-story home is shown, surrounded by lush greenery and mature trees. A wooden deck with railings is featured at the entrance, overlooking a pathway made of stones, while a large tree stands prominently beside the house.

Home in Ocean Pines

Cozy Corner Retreat

4.89 out of 5 average rating, 76 reviews

The cottage exterior features a welcoming design with a red front door, surrounded by a gravel pathway and lush greenery. Large windows brighten the facade, while a porch with railings offers a relaxing space to enjoy nature.

Cottage in Selbyville

"Bayside" Coastal Cottage w/ Golf, Hot Tub + EV

4.58 out of 5 average rating, 12 reviews

A charming ranch-style home is set against a backdrop of greenery, featuring a welcoming front deck with seating. The light-colored exterior is complemented by clear glass windows and a decorative front door. A well-maintained lawn and pathway enhance the inviting curb appeal.

Home in Ocean Pines

Pet-friendly home with private fenced backyard!

5.0 out of 5 average rating, 19 reviews

Condo in Ocean City

Views from the ocean to the bay!

5.0 out of 5 average rating, 8 reviews

Home in Selbyville

The Sun Dance, Keenwik on the Bay