Pet-friendly holiday rentals in Chincoteague

4.98 out of 5 average rating, 161 reviews

A charming cottage stands surrounded by lush grass, with a large tree providing shade in the foreground. The white exterior features a welcoming entrance with step access, flanked by neatly trimmed bushes and colorful potted plants. A serene open field extends beyond the cottage.

Cottage in Greenbush

Bell Farm Cottage Quiet, Tranquil and Peaceful

Cozy cottage located on a quiet backroad overlooking a wide open field with a deck that provides warm & sunny space for relaxing or reading a book. BFC has a warm farm house feel w/ a touch of the beach. Our kitchen is fully equipped w/ all you need to cook. BFC is located only a few miles from both seaside and bayside boat ramps. A 5 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wachapreague, Wallops & Chincoteague are just a short drive away.

Outdoor spacesHospitalityCheck-in

4.94 out of 5 average rating, 541 reviews

Tiny home in Accomac

Little Red House on a Rural Farm for Stargazing

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 13+ years

WalkabilityOutdoor spacesBarbecue

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 🌄

PetsOutdoor spacesAmenities

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!

WalkabilityOutdoor spacesCheck-in

4.94 out of 5 average rating, 191 reviews

A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.

Cottage in Onancock

A "True" Chesapeake Bay Waterfront Experience!

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 "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

Outdoor spacesPetsTV

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!

WalkabilityPetsTV

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.

Outdoor spacesWalkabilityBiking

4.88 out of 5 average rating, 185 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!

Outdoor spacesPetsNearby

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.

PetsOutdoor spacesBathroom

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.

PetsOutdoor spacesCheckout

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.

PetsOutdoor spacesView

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.

WalkabilityOutdoor spacesCondition

Popular amenities for Chincoteague pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 161 reviews

Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.

Home in Belle Haven

Bay Breeze Home on private waterfront

PetsWalkabilityValue

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

PetsWalkabilityAccess

4.89 out of 5 average rating, 192 reviews

A spacious waterfront home is set amidst a large yard, featuring green grass and landscaped flower beds. Trees provide shade around the property, while the water glistens in the background. A covered porch invites relaxation, enhancing the outdoor living space.

Home in Reedville

Gorgeous Views! 150 ft private beach/Dock

PetsOutdoor spacesKitchen

4.93 out of 5 average rating, 196 reviews

A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.

Home in Woolford

Waterfront Getaway with Dock

Outdoor spacesWalkabilityGetting around

4.95 out of 5 average rating, 198 reviews

A serene waterfront scene is captured at sunset, showing gentle waves reflecting the colorful sky. A private dock is visible, extending into the calm water, surrounded by lush greenery. The tranquil environment highlights the natural beauty of Cockrell's Creek.

Home in Reedville

Secluded, Waterfront: Fire pit, Game Room, Kayaks!

Outdoor spacesWalkabilityHeating

4.88 out of 5 average rating, 198 reviews

A quaint house exterior features a gravel pathway leading to a covered porch. A wooden fence encloses a landscaped area with bushes and flowers. Two chairs are positioned on the porch, and a grill can be seen nearby, providing opportunities for outdoor relaxation.

Home in Parsonsburg

Forest Grove Retreat

Outdoor spacesPetsFamily

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.

WalkabilityPetsAmenities

5.0 out of 5 average rating, 25 reviews

New house, Bay views, 4 Beds, Game room

PetsOutdoor spacesCleanliness

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 222 reviews

Cottage in Berlin

Bayfront Cottage w/ Amazing Views

PetsOutdoor spacesAccess

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

Outdoor spacesPetsBathroom

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

Outdoor spacesPetsCondition

4.95 out of 5 average rating, 124 reviews

Superhost

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!

Outdoor spacesWalkabilityComfort

4.83 out of 5 average rating, 109 reviews

4.98 out of 5 average rating, 162 reviews

A vibrant pot of red flowers is positioned in the foreground, with a wooden deck leading to a clear blue pool in the background. The pool area features a white fence and steps, surrounded by greenery and a cloudy sky above.

Home in Ocean City

Stunning Bayview Home with Own Private Pool

Outdoor spacesWalkabilityIndoor spaces

4.99 out of 5 average rating, 139 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

PetsWalkabilityValue

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

PetsOutdoor spacesCheckout

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

Outdoor spacesWalkabilityCondition

Private, pet-friendly home rentals

4.92 out of 5 average rating, 236 reviews

A serene view of a cove with gentle waves lapping against a sandy shore. The calm water reflects the clear blue sky and nearby greenery. Footprints are visible in the sand, leading toward the water's edge.

Cottage in Reedville

"Dragonfly" Waterfront Cottage on Chesapeake Bay

PetsOutdoor spacesHot tub

Guest suite in Fenwick Island

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.

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

WalkabilityOutdoor spacesValue

4.83 out of 5 average rating, 136 reviews

The spacious kitchen features light blue cabinetry and a large countertop. Modern appliances, including a refrigerator, oven, and dishwasher, are visible. A window allows natural light to enter, and a small rug lies in front of the sink area, adding a touch of comfort.

5.0 out of 5 average rating, 13 reviews

Willow Haven

Outdoor spacesPetsCleanliness

4.89 out of 5 average rating, 74 reviews

The open-plan living area features rich wooden beams and elegant flooring. A cozy fireplace with a stone surround stands beside a modern sofa. A dining area is visible, with a large table and chairs, while a staircase leads to the upper level.

Home in Berlin

Shire Retreat - Berlin, Assateague, Ocean City

WalkabilityPetsDecor

4.91 out of 5 average rating, 46 reviews

Cottage in Melfa

Waterfront 1BR on Working Farm w/ Deck + View

WalkabilityOutdoor spacesLocation

4.96 out of 5 average rating, 74 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.

WalkabilityOutdoor spacesCheck-in

4.96 out of 5 average rating, 71 reviews

A three-story home is showcased at sunset, reflecting beautifully in the calm water. Wraparound porches provide shaded areas, and nearby greenery enhances the natural setting. The tranquil surroundings suggest a serene atmosphere for relaxation.

Home in Smith Island

Island Time (whole house rental)

PetsWalkabilityIndoor spaces