Pet-friendly holiday rentals in Cape Charles

4.94 out of 5 average rating, 513 reviews

A quaint tiny house presents a welcoming exterior with a red facade and inviting black door. Comfortable seating is arranged on green grass under a large white umbrella, surrounded by planters with flowers. Lush greenery and a pathway enhance the serene outdoor setting.

Tiny home in Accomac

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

4.9 out of 5 average rating, 132 reviews

Home in Buckroe Beach

Cozy-Home! Close to Beach. Kid, Dog Friendly.

ADORABLE BEACH-HOUSE! ONLY 1.4 Miles to Buckroe Beach! BACK YARD FIRE-PIT. SHADE. FAST INTERNET. GARAGE w/ WORKOUT SPACE HAVE a blast at this adorable kid & dog friendly home. Fully Furnished and Updated. Beautiful kitchen with stainless appliances opens to family room with 65" Roku TV and blazing internet. On-site Laundry. Room darkening shades. Quiet neighborhood. Garage with workout bench and dumbbells. Back yard with sail-shade, chairs, grill and fire-pit. Make this your GETAWAY home!!!

Place to stay in White Stone

The image captures a waterfront view of the lighthouse-style home set on a spacious lot. A private dock extends into the water, featuring a vibrant red umbrella providing shade over seating. Surrounding lush trees add to the serene outdoor setting.

5 out of 5 average rating, 106 reviews

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King

Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

4.99 out of 5 average rating, 303 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!

4.94 out of 5 average rating, 177 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!

4.97 out of 5 average rating, 130 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

On Virginia's beautiful Eastern Shore, the Bay Breeze Home on Occohannock Creek is the ultimate getaway for two or a large family desiring outside adventures. This 1970's spacious home has plenty of room. Experience the water with our three kayaks or family canoe and watch the abundant wildlife. Right outside your door, you may see Ospreys, Great Blue Herons, Eagles, wild ducks, porpoises, deer, geese, otters, & more. Be our guest and forget your worries in this spacious and serene spot.

The exterior of the cottage features a charming design with a sloped roof and textured blue siding. A welcoming porch is supported by white railings, inviting visitors to relax. Surrounding greenery adds to the serene atmosphere, complemented by clear skies overhead.

4.98 out of 5 average rating, 264 reviews

Bay Breeze on Tazewell (Sun-Sun rental June-Aug.)

Bay Breeze on Tazewell is a recently remodeled Cassatt cottage with historic charm and modern amenities. The home includes a fabulous, sunny kitchen stocked to meet your needs. We provide fresh linens and towels for your stay. In the shed, you will find lots of items for the beach, a wagon, and bikes which we are happy to share. Bay Breeze is just a short walk to the beach, various restaurants, boutiques, and marina. If our home is not available, try our new Airbnb home ...Harbor View!

4.95 out of 5 average rating, 203 reviews

The interior of the tiny cabin showcases a unique staircase leading to a lofted sleeping area. Natural wood elements are highlighted throughout, with a clear roof allowing natural light to fill the space. A doorway opens to the outdoors, enhancing the cabin's connection to nature.

Tiny home in Diggs

Stargazer Tiny Cabin

(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

4.99 out of 5 average rating, 128 reviews

An inviting outdoor fire pit area features turquoise Adirondack chairs arranged around a stone fire ring. The charming blue farmhouse, with a metal roof, is partially shaded by trees, and sprawling green grass surrounds the property, enhancing the space for relaxation.

Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

Tiny home in Cape Charles

A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.

4.98 out of 5 average rating, 339 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

4.91 out of 5 average rating, 212 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

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!

4.96 out of 5 average rating, 207 reviews

A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.

Cabin in Cape Charles

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Popular amenities for Cape Charles pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.99 out of 5 average rating, 101 reviews

The exterior of a two-story, light blue house is presented, featuring a covered front porch with multiple seating options. Dormer windows complement the structure, and a garage is visible on the left side. Lush greenery frames the home, enhancing its serene setting.

Home in Reedville

Nautical Farmhouse Reedville VA, Sleeps 8 / 3 Bdrm

A two-story blue house is framed by white trim and windows, showcasing a welcoming front porch and a white picket fence. A golf cart is conveniently parked in front, with a patio umbrella visible on the side, indicating outdoor leisure space.

4.95 out of 5 average rating, 87 reviews

Historic, Pet Friendly Cottage-Three Little Birds

5 out of 5 average rating, 15 reviews

The exterior of a spacious house displays a multi-level design with a sloping roof and large windows. Balconies adorn the upper levels, offering outdoor seating areas. Lush green trees surround the property, enhancing the natural appeal of the waterfront setting.

Home in Onemo

Spacious waterfront home, private dock

The living area features a comfortable seating arrangement with a neutral-colored sofa and an accent chair. A textured area rug sits beneath a rustic coffee table. Light from nearby windows illuminates the room, complemented by a modern fireplace and a wall-mounted television.

4.92 out of 5 average rating, 24 reviews

Lil Ms. Clementine-Historic District Golfcart opt.

A historic two-story duplex features a light-colored exterior with four large windows on the upper floor. Two entrances are visible on the lower level, flanked by two American flags. A small garden area lines the front, with a tidy walkway leading to the steps.

4.87 out of 5 average rating, 15 reviews

Sea Glass Hideaway | B

4.84 out of 5 average rating, 382 reviews

A spacious home is depicted with a welcoming front porch featuring a gentle ramp for accessibility. Lush greenery surrounds the exterior, and the peaceful atmosphere is enhanced by the colorful sunset sky. The house showcases a combination of brick and siding with large windows.

Home in Coliseum Central

Family Holiday House. Events and Beaches Nearby

4.95 out of 5 average rating, 38 reviews

A charming cottage is depicted, framed by lush green grass and mature trees. The front features a covered porch with multiple large windows, allowing for ample natural light. A serene atmosphere is created by the surrounding open space, inviting relaxation and connection to nature.

Home in Port Haywood

Relax & Heal Cottage Near Ocean & Forest Retreat

4.93 out of 5 average rating, 109 reviews

A waterfront home is depicted with a blue exterior and a welcoming front porch featuring Adirondack chairs. Lush greenery surrounds the property, and a rocky shoreline is visible in the foreground. The serene setting is complemented by clear skies and distant trees.

Home in Kilmarnock

Waterman's Waypoint

Pet-friendly home rentals with a pool

A large two-story home is framed by lush greenery, featuring multiple windows on its upper level that allow natural light to fill the interior. A welcoming front porch with steps leads to the entrance, showcasing the spacious design of the residence.

Bay Dunes

Campervan/RV in Belle Haven

An Airstream trailer is parked on a gravel surface, showcasing its polished exterior. A large blue and white geometric-patterned rug is positioned in front, accompanied by a wooden stump serving as a small table. A bouquet of flowers adds a touch of color nearby.

5 out of 5 average rating, 15 reviews

Belle Haven’s Bliss

5 out of 5 average rating, 9 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

An expansive outdoor space features a fenced swimming pool, surrounded by well-maintained gardens with various shrubs and blooming flowers. The backdrop includes a serene view of the water and trees, creating a peaceful environment perfect for relaxation.

Home in Exmore

4.73 out of 5 average rating, 30 reviews

Bayfront Retreat w/ Game Room + Outdoor Pool!

A circular arrangement of stone seating surrounds a sandy fire pit area, offering a cozy gathering space. In the background, a spacious heated saltwater pool glimmers under sunlight, bordered by lush greenery and shaded by trees.

Home in Phoebus

4.83 out of 5 average rating, 217 reviews

Waterfront home with heated pool available!

A modern three-story beach house is showcased, featuring clean lines and a crisp white and navy color scheme. Large balconies with railings extend across the front. Two garage doors are visible on the lower level, framed by a neat driveway and landscaped greenery.

Retreat from the busy city to this beach getaway.

4.89 out of 5 average rating, 18 reviews

A welcoming home features large windows overlooking a glistening pool, which invites relaxation. Several lounge chairs are positioned around the pool area, and an umbrella provides shade. The wooden deck extends from the house, enhancing the outdoor space.

Holiday home in Burgess

Northern Neck Waterfront

A two-story blue house with white trim and black shutters is showcased. A covered porch is featured at the front, surrounded by manicured hedges and a spacious lawn. Neighboring houses are visible in the background under a clear blue sky.

4.77 out of 5 average rating, 31 reviews

Sunshine Baydream Cape Charles

Private, pet-friendly home rentals

4.99 out of 5 average rating, 84 reviews

The farmhouse exterior features vibrant red siding and multiple large windows, allowing natural light to fill the interior. Two Adirondack chairs are positioned in the front yard, with bicycles visible nearby. Lush greenery surrounds the property, enhancing its secluded ambiance.

Cottage in Cape Charles

The Ladybug - arcade, dog-friendly, firepit, & EV

Apartment in Cape Charles

A state-of-the-art kitchen features bold crimson red cabinetry and a vintage-style refrigerator. Smeg appliances are included, enhancing the 1950s-inspired design. A large island with a white countertop offers ample space for preparation, while a large-screen TV is mounted on the wall.

4.95 out of 5 average rating, 21 reviews

Historic Charm & Modern Comfort : Downtown Escape

Townhouse in Downtown Hampton

A spacious living room features a large sectional sofa adorned with colorful cushions. A small blue side table complements the decor. Natural light filters through the windows, illuminating the room's modern art pieces and wood flooring.

4.68 out of 5 average rating, 314 reviews

Downtown Oasis, Walkers Paradise! Near Marina+

5 out of 5 average rating, 21 reviews

The entrance features a set of steps leading up to a screened porch, illuminated by warm lighting. Lush plants are situated beside the stairs. Two decorative dogs stand on either side of the entrance, adding charm to the welcoming facade.

Home in White Stone

The Guesthouse

4.9 out of 5 average rating, 51 reviews

A cozy bungalow is framed by lush greenery, featuring a path leading to the entrance. In the front yard, a small round table and two red chairs are set on a stone patio, surrounded by grass and shaded by trees.

Bungalow in Accomac

Cozy shore bungalow

4.99 out of 5 average rating, 85 reviews

The inviting exterior of the house features a bright pink door and a cheerful American flag. Two decorative dogs are positioned near the entrance, surrounded by a wrap-around porch adorned with turquoise chairs and potted plants. The front yard is landscaped with a grassy area.

Cottage in Cape Charles

Dog friendly, large fenced yard! 1st Floor Bedroom

4.95 out of 5 average rating, 55 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 cabin with creek view.