Pet-friendly vacation rentals in Cape Charles

A front porch features a welcoming blue door and cozy seating area with two chairs and a swing. Pillows adorn the chairs, creating a comfortable spot to relax. The porch is surrounded by white railings and offers a glimpse of the neighborhood.

4.99 out of 5 average rating, 106 reviews

Walk 2 Beach & Restaurants~Central Park~ King Bed!

You will be close to everything in Cape Charles! Experience a fully renovated 1900’s Victorian duplex centrally-located! Next to the park, 2 quick blocks to Main St. & beach! The upstairs bedrooms share a Jack and Jill bathroom. Full kitchen with washer/dryer. 2 outdoor living areas to sip your coffee or wine! Your family will feel cozy and relaxed while you're on vacation! • Front Porch Swing & Backyard Brick Patio w/Grill • Beach Gear, Games, Pickleball • Modern Kitchen, Wood Floors, King Bed

Townhouse in Cape Charles

The living area features a cozy gray sofa, two armchairs, and a circular coffee table. Natural light fills the space through windows adorned with light curtains. A large wall-mounted TV is positioned above a white media console, enhancing the room's modern yet inviting aesthetic.

Walk to Beach and Park! Outdoor shower&Fenced Yard

Welcome to Peach Haven, a newly renovated duplex in the Cape Charles historic district. Just 1 block from the park and 3 blocks from the beach, it's the ideal base for your Cape Charles escape. This pet-friendly rental sleeps four guests comfortably with a master bedroom (queen bed) and a second bedroom with a custom-made full-over-full bunkbed. The house has been thoughtfully stocked with everything you'll need for a comfortable stay. Ask about our optional golf cart rental during your stay!

4.97 out of 5 average rating, 202 reviews

A classic brick duplex features a large front porch supported by white columns. A ceiling fan hangs in the shaded area, while steps lead up to the entrance. Lush greenery lines the porch, and a clear blue sky complements the welcoming design.

4.92 out of 5 average rating, 173 reviews

Harbor View- (Sun - Sun rental June- Aug.)

Harbor View is an early 1900's brick duplex with high ceilings, transom windows, and crown molding. Best of all, this home is located in a quiet neighborhood just one block from the beach and two blocks from Mason Ave. where you can find unique shops, restaurants and other amenities. It's an easy walk to the pier for a magnificent sunset, or to Brown Dog's for homemade ice cream. We invite you to enjoy our comfortable home, and explore the quiet ambience of a historic beach town vacation!

4.99 out of 5 average rating, 352 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!

4.98 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

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.

4.96 out of 5 average rating, 265 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, feed the Alpacas, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

5.0 out of 5 average rating, 100 reviews

The exterior of a red barn is shown, surrounded by lush green fields. The structure features a peaked roof with a cupola, multiple windows, and an inviting porch area with wooden steps. The surrounding farmland creates a serene atmosphere.

Barn in Cape Charles

Coastal Red Barn Retreat

Located on the coastal seaside of Cape Charles, this barn was originally built in 1893. It has been lovingly restored to reflect the area's rich history, while providing modern comforts for today's guests. The Red Barn is nestled in the midst of scenic farmland, yet is only a few miles from the charming downtown, with its eclectic restaurants and unique shops. Enjoy the fresh breezes of the Atlantic and watch the sunrise over the fields from the comfort of the barn's private deck.

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.

4.99 out of 5 average rating, 149 reviews

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.

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.

4.98 out of 5 average rating, 363 reviews

The charming brick house features a welcoming front porch with white railings. Lush greenery and colorful blooms adorn the front yard, framed by neatly manicured shrubbery. Natural light brightens the exterior, highlighting the multi-pane windows and the peaked roof.

4.95 out of 5 average rating, 121 reviews

It’s porch season! Welcome to the MT Nest!

Welcome to The MT Nest! Relax in our charming 100 year old Sears house in the heart of historic Cape Charles. Enjoy mornings on the porch in the shade of majestic trees. Walk to the beach in the afternoon. Then stroll a few blocks to restaurants and shops in the evening. Central park across the street offers summer concerts, a playground, and a splash fountain. Enjoy the quiet and slow your life down for a few days of bliss!

A charming duplex exterior features a light yellow facade with blue shutters and a welcoming covered porch. White steps lead to two front doors, flanked by lush greenery, including flowering hydrangeas. The evening sky adds a soft hue in the background.

4.94 out of 5 average rating, 127 reviews

The Shore House on Madison - Pet Friendly Unit!

The Shore House on Madison was fully renovated in 2019 and located in the Cape Charles Historic District within walking distance to the beach, park, the shops and restaurants. Our pet friendly unit can host up to 7 guests with 3 bedrooms, 2 full baths and 1 outdoor shower. Bedroom #1 includes 1 Queen bed, TV and work desk. Bedroom #2: 1 Queen bed. Bedroom #3: Bunk Bed (1 double / 1 twin). Fenced in backyard with patio.

Popular amenities for Cape Charles pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly home rentals with a pool

4.87 out of 5 average rating, 141 reviews

Home in Hampton

4BD home w/ game room & pool near Langley & PTC!

4.87 out of 5 average rating, 155 reviews

Camper/RV in White Stone

“Old Smokey”A cozy, single bedroom, unique getaway

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.

5.0 out of 5 average rating, 4 reviews

6 BR Home w/Private Beach + Community Pool

Townhouse in Cape Charles

The exterior of a spacious townhome is framed by lush greenery and manicured lawns. The structure features a mix of light-colored siding and brick accents, with two attached garages. Large windows allow for natural light, and a welcoming front porch is visible under an overhanging roof.

Family Beach Vacation with Access to Book Golf in

5.0 out of 5 average rating, 7 reviews

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

5.0 out of 5 average rating, 13 reviews

Home in White Stone

Cedars View

4.87 out of 5 average rating, 15 reviews

A brick exterior home is presented with a well-maintained lawn and mature trees surrounding the property. A porch accommodates seating, while a driveway leads to a single-car garage. The front yard is landscaped with potted plants, enhancing the inviting appearance of the entrance.

Home in Buckroe Beach

ShowTyme's Hampton Oasis

Home in Exmore

Bayfront Retreat w/ Game Room + Outdoor Pool!

4.78 out of 5 average rating, 36 reviews

Pet-friendly home rentals with a hot tub

4.89 out of 5 average rating, 266 reviews

A hot tub is positioned on a wooden deck, overlooking the shimmering waters of the Chesapeake Bay. Surrounding greenery includes tall grasses and trees, with the expansive view of the water framed by a clear blue sky.

Cottage in Reedville

Bay cottage 🏖on the beach. Stunning views🏝

4.91 out of 5 average rating, 183 reviews

Home in Cobbs Creek

Million $ Views! Pool! Private Hot Tub! EV Charger

4.91 out of 5 average rating, 110 reviews

Home in Norfolk

Walk to Beach | Hot Tub + Games | Pet Friendly

4.95 out of 5 average rating, 106 reviews

A spacious living area features two light-colored sofas adorned with decorative pillows. A wooden coffee table sits centrally, topped with magazines and a vase of flowers. Soft blue walls create a calming atmosphere, complemented by a dining area visible in the background.

Home in Buckroe Beach

Buckroe Beach Luxury Home Hot Tub, Grill, Gameroom

A spacious living area features a large sectional couch, a coffee table, and a massage chair. Natural light floods the space through sliding glass doors, illuminating the wood flooring. The open layout connects to a kitchen and dining area, enhancing the communal feel.

4.94 out of 5 average rating, 64 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

5.0 out of 5 average rating, 19 reviews

Beach Bliss Cottage- Hot Tub, Golf Cart & Firepit

4.87 out of 5 average rating, 38 reviews

A spacious waterfront property is featured, showcasing expansive outdoor areas including a heated pool, playground, and large lawn. A comfortable deck surrounds the pool, while the house is adjacent to well-maintained landscaping and pathways, highlighting the scenic surroundings and inviting outdoor activities.

Home in Reedville

Bayfront | Pool Open & Heated, Hot Tub, Dock, Pets

An aerial view reveals a spacious house by the coast, surrounded by greenery. Nearby, a patio area features lounge chairs and a fire pit, while kayaks are visible beside the house. The expansive ocean can be seen in the background, enhancing the serene landscape.

4.78 out of 5 average rating, 32 reviews

Beach Front - Hot Tub - Game Room - 3500SQFT

Pet-friendly house rentals

4.89 out of 5 average rating, 369 reviews

Home in Grimstead

Gwynns Island Waterfront Getaway

4.97 out of 5 average rating, 194 reviews

A traditional brick house is depicted, featuring a symmetrical roofline and charming dormer windows. The front entrance is framed by a small porch, with a set of steps leading to the door. Lush green grass and flowering shrubs surround the home, enhancing the natural setting.

Home in Kilmarnock

PORT DITCHLEY - Northern Neck Waterfront Home

The exterior of the home features a welcoming yellow door framed by blue and white stripes. Surrounded by green foliage, the porch includes a wooden ramp for accessibility. Large windows provide a glimpse of the interiors, softly illuminated by warm lighting.

4.8 out of 5 average rating, 136 reviews

"Live Life Sunnyside Up" - Minutes From The Beach!

4.99 out of 5 average rating, 133 reviews

A beachfront home with a two-story structure is positioned on stilts, overlooking the waves of the Chesapeake Bay. Large windows reflect the vibrant blue of the sky and the inviting design of the house. Nearby houses and green grass complement the coastal setting.

Home in Buckroe Beach

Beachfront 2 Dwellings EV charger

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!

4.96 out of 5 average rating, 26 reviews

4BR, Pet-Friendly, 1st Fl Suite

A three-story brick home is set among manicured greenery, featuring a covered entrance supported by arches. A spacious balcony extends across the upper level, adorned with white railings. Several windows, arranged symmetrically, offer a classic architectural appearance with charming outdoor elements.

5.0 out of 5 average rating, 42 reviews

Chesapeake Bay View