Family-friendly holiday rentals in Chincoteague

Guest suite in Chincoteague

A cozy bedroom features a white, wooden bed frame with a floral-patterned coverlet. Two pillows and a decorative cushion rest against the headboard. A bedside table holds a lamp, and natural light enters through a window with soft curtains.

4.94 out of 5 average rating, 338 reviews

Baywatch North-Waterfront & Roaming Ponies

Calender open for super deals on weekly Summer rentals 2026. Lovely space! 2 queen bdrm unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

4.93 out of 5 average rating, 133 reviews

Dragonfli Bay House on Chincoteague Island

Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayaking on the bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

4.94 out of 5 average rating, 512 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

A light-filled living room is presented with soft beige seating arranged around a round, patterned coffee table. A landscape artwork adorns the wall above the couch. Natural light streams through a nearby window, highlighting a plant tucked in the corner.

4.93 out of 5 average rating, 178 reviews

Adorable Beach Cottage Just Steps From Town & Bay

New to AirBNB! Welcome to Wiggle Bay, a darling 1955 2 BR cottage nestled in the heart of "one of the most beautiful, charming small towns in Virginia." -Enjoy a bay breeze on the screened front porch--heaven! --Stroll to local bookshop, coffee house, theatre, or Chincoteague Waterfront Park to feed the ducks--all just steps from your front door! -Situated on a quiet residential street -Just 4 blocks to Maddox Blvd (where all the action is) -2.3 mi to Assateague Seashore/Chincoteague Refuge

4.99 out of 5 average rating, 265 reviews

A welcoming space is featured, showcasing a luxurious jacuzzi with a wooden tray holding candles and decor. Nearby, a cozy living area with a modern couch is highlighted against an artistic forest mural. An adorable Highland cow stands nearby, adding a touch of rustic charm.

Farm in Selbyville

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

4.99 out of 5 average rating, 300 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!

4.99 out of 5 average rating, 196 reviews

A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.

Cottage in Frankford

19th Century Cottage with Modern Amenities

Book your Hallmark Christmas stay today, fully decorated by Thanksgiving until the end of January!! Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

A charming two-story island home is nestled among tall trees, providing a natural setting. The structure features a sloped roof and a front porch with a railing. Sunlight filters through the branches, casting dappled shadows on the ground.

4.97 out of 5 average rating, 181 reviews

Charming Island Home "Sandy Pines"

Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is). The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

4.98 out of 5 average rating, 113 reviews

A modern barn-style exterior is shown with a soft twilight glow. Inside, a cozy loft bedroom features a spacious bed adorned with decorative pillows. A bright dining area is visible, highlighting wooden accents and seating. Two playful goats are seen exploring their cozy enclosure.

Loft in Pocomoke City

Cozy Barn Loft: Country Views & Central to Beaches

Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.

4.96 out of 5 average rating, 281 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

4.87 out of 5 average rating, 157 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

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

4.77 out of 5 average rating, 240 reviews

The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.

Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Popular amenities for Chincoteague family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious living area features a large wall-mounted entertainment center with a flat-screen TV. Comfortable seating options include a striped sofa and a patterned armchair. Sliding glass doors provide unobstructed ocean views and natural light, enhancing the inviting atmosphere of the space.

4.84 out of 5 average rating, 102 reviews

Luxurious Oceanfront Retreat with Amazing Views!

4.97 out of 5 average rating, 117 reviews

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.

Home in Cape Charles

Wander Cape Charles

4.93 out of 5 average rating, 158 reviews

A spacious living area features a large sectional sofa adorned with blue accent pillows. Exposed wooden beams grace the ceiling, while a light wooden floor complements the dark furnishings. A coffee table sits centrally, and a modern kitchen can be seen in the background.

Townhouse in Ocean City

Beach, Boardwalk n Fun- just steps to the beach

A comfortable living area features a light-colored table surrounded by ocean-themed upholstered seating. Large glass doors allow natural light to fill the space while offering a view of the balcony and ocean beyond. A flat-screen television is mounted on the wall.

4.9 out of 5 average rating, 116 reviews

Oceanfront Carousel building, Swimming Pools!

4.99 out of 5 average rating, 130 reviews

A spacious waterfront home is showcased, featuring a large porch and neatly manicured lawns. The property includes a sandy beach leading to the calm waters of Fishing Creek, with a picturesque background of trees and a second building in the distance.

Home in Woolford

Starboard on McKeil Point, w/heated pool & hot tub

4.88 out of 5 average rating, 189 reviews

A circular swimming pool is surrounded by sun loungers and shaded umbrellas, inviting relaxation. The beach lies in the background, with a stretch of sandy shore and blue umbrellas, while guests enjoy the sun and water nearby.

Condo in Bethany Beach

Beautiful Beach-View Condo

4.94 out of 5 average rating, 161 reviews

A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

Home in Cambridge

Peaceful Historic House Near Water, with Hot Tub!

4.9 out of 5 average rating, 230 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🏝

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 151 reviews

The interior of the bus features a cozy layout with wood paneling and large windows providing natural light. A comfortable seating area, equipped with pillows, is situated next to a compact kitchen with a stove and cabinets. A small dining table with two placemats is visible.

Bus in Frankford

Delightful Skoolie Near Bethany Beach

4.95 out of 5 average rating, 254 reviews

A tranquil waterside view is captured at sunset, showcasing vibrant colors reflecting on the calm water. A private dock extends into the water, with boats gently bobbing alongside. Lush trees frame the scene, enhancing the serene atmosphere.

Home in Reedville

Waterfront FamilyFriendly Home Improved for 2023

4.83 out of 5 average rating, 179 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

4.87 out of 5 average rating, 180 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

Campervan/RV 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

4.93 out of 5 average rating, 153 reviews

The image captures a serene sunset over water, with a shared pier extending into the view. Silhouettes of individuals can be seen near the pier, while golden and orange hues blend with dark clouds in the sky, creating a tranquil and scenic atmosphere.

Cottage in Deal Island

Water View Cottage

Apartment in Church Creek

A bright dining area features a wooden table surrounded by four chairs, illuminated by natural light from the sliding glass doors. A cozy armchair with a soft throw blanket is present, with a clock and decorative art pieces on the walls, creating a welcoming atmosphere.

4.97 out of 5 average rating, 429 reviews

Nature's Rest in Church Creek

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.

4.91 out of 5 average rating, 200 reviews

Rest A'Shored charming Chincoteague getaway

Family-friendly home rentals with a pool

The living room features a large window providing stunning ocean views. Two turquoise chairs and a comfortable blue sofa are arranged around a wooden coffee table. A patterned rug adds visual interest to the space, while a flat-screen television is mounted on the wall.

4.93 out of 5 average rating, 137 reviews

Oceanfront 2 Bed/1.5 Bath, Balcony, Pools, Lounge

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

4.83 out of 5 average rating, 155 reviews

Tiny home in Millsboro

Farm Cottage - POOL - 30 Min to BEACH

4.93 out of 5 average rating, 105 reviews

The cottage is presented in a well-maintained landscape, featuring a light-colored exterior with dark shutters and a welcoming front door. Two benches sit on either side of the entrance, with potted plants nearby and a lush green lawn extending into a wooded area behind.

Farm stay in Pittsville

Kits Cottage on "Just Ducky Acres"

An open living area is highlighted by large windows that offer views of the bay and pool. A comfortable sectional sofa is positioned adjacent to a smart TV, while a modern dining table for four is visible next to the kitchen. The space features light-colored walls and natural wood flooring.

4.96 out of 5 average rating, 107 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

4.97 out of 5 average rating, 197 reviews

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Condo in Ocean Pines

Pines Getaway - Berlin Tree Light & Ice Ice 11/28

4.99 out of 5 average rating, 102 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

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines