Pet-friendly holiday rentals in Cape Charles

4.98 out of 5 average rating, 223 reviews

A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.

Flat in Newport News

Centrally Located Sleek Studio Apartment

Private guest studio apartment with separate parking/entrance in a quiet neighborhood. Centrally located to shopping, restaurants , and parks. Airport:12 min CNU:6 min Riverside Medical Center:7 min Sentara Hospital:8 min Langley AFB:11 min Patrick Henry Mall:8 min Willimasburg/Bush Gardens: approx 30 min Virgina Beach Oceanfront: 45 min Wifi available with a 55" TV with streaming services (no cable). Coffee table folds into dining/work table. Stools under table. Full bath/kitchen/laundry unit.

4.94 out of 5 average rating, 511 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

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, 104 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, 123 reviews

The view from the entrance displays a spacious deck leading to the water, framed by sturdy wooden supports. Two large doors provide access and natural light, highlighting the inviting outdoor space with chairs positioned for relaxation.

Cottage in Weems

The Crab Shack

Enjoy the sunrise at this unique and tranquil getaway! This property was originally a seafood processing facility...hence The Crab Shack! Watch all the action on the water right out the front door with local waterman in and out of beautiful Carter's Creek to and from the Rappahannock River and Chesapeake Bay. There are marinas and The Tides Inn very close by. This property provides privacy and a short 10 minute drive to nearby restaurants and shops in Irvington, Kilmarnock, and White Stone.

4.99 out of 5 average rating, 297 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!

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, 260 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!

Cottage in East Ocean View

A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.

4.99 out of 5 average rating, 274 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

A spacious great room features high, vaulted wooden ceilings. A modern chandelier complements the textured stone fireplace, while two comfortable sofas are accented with soft throws. Surfboards are displayed on the wall, and a large coffee table showcases decorative items and a natural centerpiece.

4.97 out of 5 average rating, 117 reviews

Wander Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

4.97 out of 5 average rating, 154 reviews

Two classic white Adirondack chairs are positioned on a grassy bank overlooking the calm water of the Rappahannock River, framed by gently swaying trees. The sky displays a soft transition of colors as the sun sets, creating a serene and inviting view.

Home in Locust Hill

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

4.97 out of 5 average rating, 250 reviews

A charming cottage is set against a backdrop of tall trees, showcasing a light-colored exterior. A welcoming front porch features comfortable seating and an American flag. The landscaped yard includes potted plants and a gravel pathway leading to the entrance.

Cottage in Gloucester

"Bee Haven" Cottage Retreat

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

4.99 out of 5 average rating, 125 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.

Popular amenities for Cape Charles pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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, 86 reviews

Historic, Pet Friendly Cottage-Three Little Birds

A renovated Victorian house is displayed, featuring a welcoming front porch with comfortable seating. Lush greenery and flower planters accompany the entrance. Light-colored siding contrasts with a bold red roof, and large windows allow ample natural light to illuminate the inviting space.

4.94 out of 5 average rating, 68 reviews

The Grand Escape - Featured on HGTV

4.99 out of 5 average rating, 247 reviews

A remodeled brick home is situated on a spacious lawn, showcasing a welcoming front entrance with steps leading to the door. Lush greenery lines the property, and a sunroom extends from one side, offering views of the surrounding area.

Home in Lancaster

Rivah View

4.92 out of 5 average rating, 206 reviews

A living area features a dark sectional sofa with a decorative pillow and a coffee table with a patterned surface. A soft area rug covers the hardwood floor. Light flows in through glass doors that lead to an outdoor space, while ceiling fans provide additional comfort.

Home in East Ocean View

@Whit’s End? Come in and Relax

4.88 out of 5 average rating, 154 reviews

The exterior of the beach house is captured on a sunny day, featuring a two-story structure with upper and lower decks surrounded by a large green lawn. An American flag gently flutters in the breeze, and parking space is available nearby.

Home in Mathews

Piper’s Landing: Relaxing beach house near the Bay

4.95 out of 5 average rating, 124 reviews

A cozy living room features wood-paneled walls and a deep blue sectional sofa. A large smart TV is mounted on the wall, displaying a scenic outdoor image. An electric fireplace adds warmth, while natural light pours in through nearby windows, enhancing the inviting space.

Home in Mathews

Family Friendly Home-Fire Pit-Walk 2 Town-King Bed

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.

4.91 out of 5 average rating, 23 reviews

Lil Ms. Clementine-Historic District Golfcart opt.

The exterior of a blue house features a welcoming porch with two teal chairs. Yellow flowers grow in front of the steps, adding a pop of color to the landscape. A grassy area and trees provide a natural backdrop, enhancing the serene environment.

5 out of 5 average rating, 18 reviews

Fisherman's Getaway

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 270 reviews

Cottage in Bayview

Positano Villa

Campervan/Motorhome 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

4.96 out of 5 average rating, 70 reviews

A cozy living area features a brown sofa adorned with decorative pillows against a warm yellow wall. A small desk holds books and a decorative item, while natural light fills the space through sheer curtains. A doorway leads to a bathroom area.

Home in East Ocean View

The Seaglass Cottage

4.92 out of 5 average rating, 118 reviews

A two-story house features a light-colored exterior with a peaked roof. A spacious driveway leads to a garage door, framed by manicured grass and trees. A balcony extends from the top floor, providing outdoor space above the ground level.

Home in Norfolk

Gorgeous Vacation House

4.8 out of 5 average rating, 158 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

4.99 out of 5 average rating, 121 reviews

The entrance to The Rosé Retreat features a welcoming porch with multiple chairs arranged for relaxation. Arching glass doors provide a view into the inviting interior, framed by decorative wreaths that add a touch of seasonal charm. Lush green foliage surrounds the exterior.

Home in Irvington

The Rosé Retreat: Kayaks-Screened Porch-RELAX

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

Campervan/Motorhome in White Stone

A vintage pull-behind camper sits by the water's edge, featuring a striking teal color that contrasts with the clear blue sky. Grassy surroundings provide a natural setting, inviting views of the serene shoreline and distant water.

4.88 out of 5 average rating, 137 reviews

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

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

5 out of 5 average rating, 29 reviews

The exterior of a two-story cottage is presented, featuring a grey facade and a welcoming porch with white railings. A large tree provides shade, while chairs are arranged on the lawn. The surrounding greenery enhances the family-friendly atmosphere.

Cottage in Cape Charles

Holiday-Ready 3BR | Fire Pit Nights Wood Included!

Holiday home in Cape Charles

A charming bungalow is embraced by lush greenery and colorful flowers, featuring a welcoming front porch with seating. A palm tree adds a tropical touch, while the pathway leads to the entrance, inviting guests to explore the comforts within.

5 out of 5 average rating, 74 reviews

Down By The Bay - Cape Charles -1st Floor Primary

4.96 out of 5 average rating, 207 reviews

A unique cabin design features a distinctive red wheelhouse structure connected to a spacious gray exterior. A wooden deck surrounds the cabin, with outdoor seating and a patio umbrella visible. The setting is surrounded by trees, creating a serene, woodsy atmosphere.

Tiny home in Deltaville

Nan's Place aka Down Easter

4.94 out of 5 average rating, 18 reviews

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.

Flat in Cape Charles

Historic Charm & Modern Comfort : Downtown Escape

4.9 out of 5 average rating, 107 reviews

A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.

Cottage in Painter

Cottage by the bay (private peaceful surroundings)

4.97 out of 5 average rating, 34 reviews

The exterior of a two-story cottage features light green siding and white trim. A spacious front porch is visible, furnished with white seating. Red brick steps lead to the porch, accompanied by fresh landscaping and a clear blue sky above.

Cottage in Cape Charles

Key Lime Cottage - Your Beachside Retreat