Family-friendly holiday rentals in Chincoteague

A cozy cottage exterior is presented with a light blue façade and a welcoming front porch. The entrance features a small overhang and steps leading to the front door, accompanied by neatly trimmed bushes and a well-maintained lawn under clear blue skies.

4.94 out of 5 average rating, 208 reviews

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

Indoor spacesKitchenValue

4.94 out of 5 average rating, 540 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 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 12+ years

KitchenFamilyGrill

4.96 out of 5 average rating, 104 reviews

Island House: Kayaks, Bikes, Beach Gear & Firepit

Welcome to Happy Ours! Relax with the whole family at this peaceful Chincoteague home. Walk to the park (Pony Swim!). This beachy cottage offers all the charm with plenty of space, in a quiet area with a huge property. This is a family home that we enjoy with friends & family year-round. We would love to share that experience with you! If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Chincoteague has to offer!

Indoor spacesKitchenLaundry

4.94 out of 5 average rating, 159 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.

Indoor spacesKitchenOutdoor spaces

4.98 out of 5 average rating, 159 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.

Indoor spacesKitchenCheck-in

Adirondack chairs are arranged in a semicircle facing a stunning sunset over Chincoteague Bay. The sky reflects hues of orange and pink, while the calm waters mirror the colors above. A firepit is positioned nearby, surrounded by tall grasses.

4.96 out of 5 average rating, 168 reviews

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

Indoor spacesFamilyAir conditioning

A coastal retreat is presented in a light-colored two-story home elevated on stilts. A set of steps leads to a covered porch with a railing. A small seating area with yellow chairs is visible beneath the porch. Lush green trees surround the property.

4.98 out of 5 average rating, 120 reviews

Pearl in the Pines: bikes, kayaks, EV charger

Nestled in the shade of tall pine trees in the private community of Oyster Bay, "Pearl in the Pines" is a charming coastal retreat equipped to meet any need. This bright and beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly, making 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.

KitchenIndoor spacesBiking

4.98 out of 5 average rating, 306 reviews

A green pasture is featured, where a group of five horses graze peacefully. The background showcases a wooded area with tall trees, under a clear blue sky. A small shelter is visible in the distance, complementing the tranquil rural setting.

Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

FamilyIndoor spacesLaundry

4.84 out of 5 average rating, 108 reviews

Houseboat in Snow Hill

"Beebe Lynn" - Houseboat Getaway

A "Tiny house on the water". Your home-base for exploring Delmarva! Beebe Lynn is a vintage 32 ft Carver, nestled at Baywater Landing Marina in the stunning salt-water marshes of the Chincoteague Bay. From here, you are 35 minutes from Ocean City, MD, and 45 minutes from Chincoteague Island, VA. Beebe Lynn 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!

KitchenIndoor spacesView

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.

4.94 out of 5 average rating, 203 reviews

Adorable Beach Cottage Just Steps From Town & Bay

Escape to Wiggle Bay, a darling 1955 2 BR sunny 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! Perfectly located on a quiet street, just steps from local shops, a coffee house, and the waterfront park, where you can watch the boats, enjoy the sunset and feed the ducks. Just 2.3 mi to Assateague Seashore/Chincoteague Refuge. Ideal for a peaceful and convenient getaway!

KitchenIndoor spacesSleep quality

A modern kitchen is presented with white cabinetry and stainless-steel appliances, featuring a refrigerator, microwave, and coffee maker. A dining table is set for four, and a cozy seating area with a blue couch is visible. Natural light enters through a window, enhancing the space.

4.93 out of 5 average rating, 122 reviews

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!

KitchenFamilyView

4.95 out of 5 average rating, 194 reviews

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.

Indoor spacesKitchenBeach

Popular amenities for Chincoteague family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.86 out of 5 average rating, 128 reviews

Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

KitchenIndoor spacesQuiet

4.93 out of 5 average rating, 155 reviews

An aerial view of a serene waterfront property is depicted, showcasing a spacious home surrounded by trees. A private dock extends into the calm waters, reflecting the trees along the shoreline, highlighting the tranquil setting.

Home in Heathsville

The Hideaway at Mill Creek

FamilyKitchenBreakfast

4.98 out of 5 average rating, 311 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.

Ranch in Selbyville

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

FamilyIndoor spacesCondition

4.88 out of 5 average rating, 261 reviews

A spacious yard features a hammock suspended between two trees, overlooking the bay. Colorful Adirondack chairs are positioned nearby, creating an inviting spot for relaxation. The calm water stretches into the distance under a clear sky, providing a serene atmosphere.

Cottage in Reedville

Private point on the Bay🌤hammock, hot tub, kayaks❤️

FamilyIndoor spacesBiking

A private balcony is showcased overlooking the ocean, featuring two comfortable chairs and a small table. The scene is framed by large sliding doors, allowing natural light to brighten the space. Green turf flooring complements the outdoor seating area.

4.97 out of 5 average rating, 101 reviews

Luxury Oceanfront Oasis!

FamilyKitchenParking

Superhost

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.

4.81 out of 5 average rating, 126 reviews

Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck

FamilyKitchenSleep quality

4.99 out of 5 average rating, 141 reviews

A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.

Home in Dameron

Peace Point - Waterfront, Secluded, Home w/hot tub

FamilyIndoor spacesGrill

4.99 out of 5 average rating, 133 reviews

Home in Mathews

Garden Cottage in Downtown Mathews

KitchenIndoor spacesParking

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 232 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

FamilyKitchenHospitality

4.81 out of 5 average rating, 166 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

FamilyKitchenQuiet

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.

4.92 out of 5 average rating, 215 reviews

Rest A'Shored charming Chincoteague getaway

KitchenFamilyTV

4.99 out of 5 average rating, 141 reviews

Mins to Beach~Walk to Food and Drinks +Beach Gear!

Indoor spacesKitchenBeach

4.95 out of 5 average rating, 181 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

FamilyKitchenHospitality

4.95 out of 5 average rating, 188 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!

Indoor spacesFamilyGrill

4.99 out of 5 average rating, 344 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

KitchenFamilyBiking

4.91 out of 5 average rating, 131 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

KitchenIndoor spacesLocation

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 117 reviews

Farm stay in Pittsville

Kits Cottage on "Just Ducky Acres"

KitchenIndoor spacesQuiet

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.

4.95 out of 5 average rating, 122 reviews

Farmhouse located on a horse farm

FamilyIndoor spacesCondition

4.99 out of 5 average rating, 101 reviews

A light-filled dining area features a long wooden table surrounded by several chairs. Soft curtains frame the windows, allowing natural light to enter. A cozy seating area includes a brown leather chair and a wooden side table, enhancing the space's inviting feel.

Flat in Ocean City

Coastal 2 Bedroom Apartment w/pool

FamilyKitchenPool

4.94 out of 5 average rating, 286 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

Indoor spacesFamilyWalkability

4.99 out of 5 average rating, 117 reviews

A red barn-style building is positioned on a lush green lawn, surrounded by trees and residential structures. A porch is visible on the upper level, and a colorful wheel mural decorates the front. A gravel path leads to the entrance.

Guest house in Cambridge

The Loft at Sailor's Retreat. Waterfront Apartment

Indoor spacesFamilyBack garden

The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.

5.0 out of 5 average rating, 116 reviews

Beautiful waterview 2B condo w/Dock&Close to Beach

Indoor spacesFamilyCheck-in

4.98 out of 5 average rating, 150 reviews

The kitchen area features modern cabinetry and stainless steel appliances. A large kitchen island with seating is complemented by woven bar stools. Natural light enters through a window, enhancing the open space and inviting atmosphere.

Flat in Frankford

Sunshine By The Sea near Bethany Beach

KitchenIndoor spacesDecor

A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.