House holiday rentals in Chincoteague

4.94 out of 5 average rating, 129 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.

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, 175 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

The living area features a comfortable seating arrangement with a sofa and two chairs, all upholstered in coastal-themed fabrics. A round wooden coffee table sits centrally on a patterned rug, and large windows allow natural light to fill the space. A ceiling fan adds functionality.

4.99 out of 5 average rating, 93 reviews

Central Location-Walk 2 Dining-Recently Renovated!

Experience the ultimate in coastal living at your beautifully renovated vacation home, a stone's throw from the Beach road. This is your perfect getaway destination. You'll enjoy a bright chef's kitchen with granite countertops and a tiled backsplash, an open-concept first floor with a cozy living room, and a convenient half bath. Retire to the second level where 2 bedrooms await, including a primary suite with a private bath & private balcony for sipping your coffee & serene morning views 🌄

A cozy living area features a comfortable sectional sofa adorned with patterned cushions. A wooden coffee table is positioned in front of the sofa, complemented by a TV on a light-colored media console. Natural light filters through a nearby window, illuminating the warm wooden floors.

4.91 out of 5 average rating, 104 reviews

On a Whim, a family retreat!

Relax with the family at our home, nestled on a quiet private street yet just a short walk from restaurants, beach access, and family-friendly activities. Enjoy access to all that Chincoteague has to offer while retreating to a cozy & comfortable Cape Cod-style duplex. We are a short drive away from exploring Chincoteague National Wildlife Refuge, famous for its wild ponies and hiking trails. Whether you’re here to relax or adventure, this local gem offers something for every nature lover.

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

Spacious open floor plan great for entertaining family and friends with all the modern amenities you need! Eat inside at the large dining room table or enjoy the cool evening breeze outside on the fully screened in porch. 3 bedrooms and 2 full baths can comfortably accommodate 2 families with children or 3 couples. Located on Willow street, you are just a short walk to the Chincoteague carnival grounds and Main Street. We are dog friendly as we know they are really part of the family!

A charming cottage features a two-story structure with a white exterior and red roof accents. Balconies with railings are present on both levels, complemented by landscaped greenery and flowers at the entrance. Nearby structures are visible, creating a cozy neighborhood atmosphere.

4.85 out of 5 average rating, 115 reviews

Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

Location, Location, Location! Just a few miles from Assateague Beach & the Chincoteague National Wildlife Refuge, Sunny Claire is located in the heart of historic downtown Chincoteague Island! You are steps away from the best restaurants, shopping & other popular attractions. Relax in the 6 person hot tub & enjoy evening sunsets & partial water views from one of the cozy porches. Features: Linens for all beds & towels provided King Sleep Number Bed Outdoor Shower Water Filtration System

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, 278 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.

4.91 out of 5 average rating, 101 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

Stunning waterfront panoramic view getaway house

Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself in jaw-dropping panoramic canal views of the Chincoteague Bay. Secluded escape for the nature enthusiast, balanced with country club amenities. Pools, boating and a golf course are within walking distance. Outdoor adventures and pristine beaches are just a short drive away! This property was designed to gather, recharge, explore, love, work remotely and inspire.

A spacious family room showcases a large sectional couch in a neutral tone, complemented by decorative pillows. A TV is mounted on the wall above a modern fireplace, with natural light filtering through the window blinds.

4.9 out of 5 average rating, 115 reviews

Chincoteague Island Creekside Cottage

Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal small town". Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponys) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124". Make Memories!

4.99 out of 5 average rating, 123 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.

A charming bungalow is shown at dusk, featuring large windows that allow natural light to fill the interior. A neatly landscaped yard complements the exterior, which is painted in soft blue tones. A parking sign is visible in the foreground, indicating designated parking availability.

4.95 out of 5 average rating, 132 reviews

The Neigh-Neigh - Location, Location, Location!

Named in honor of the ponies that first put Chincoteague on the map, this charming newly renovated family getaway is walking/biking/and wheeling distance to shops, galleries, restaurants, waterfront park, library, beach, wild ponies, and movie theater. Come relax in a stunning, clean, 2 BR, 2 full BA plus oversized upstairs den with queen and twin beds and a futon bed that comfortably sleeps 8. The amenities and unique offers this place has, is not to be missed.

Popular amenities for house rentals in Chincoteague

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A cozy seating area is positioned on the waterfront, featuring plush cushions and decorative pillows. Two lanterns with candles add ambiance. Lush greenery and a clear sky are visible in the background, enhancing the serene view of the water.

4.96 out of 5 average rating, 79 reviews

Private pool, waterfront, kayaks, bikes, firepits!

5 out of 5 average rating, 105 reviews

The exterior of the single-family home is shown, featuring a welcoming entrance with a striped awning. A well-maintained front yard with shrubs and a tree provides shade, while the attached garage is visible on the left.

Home in Frankford

3BR single family house close to Bethany Beach

The kitchen area showcases wooden cabinetry and a central island, with essential appliances visible. A round dining table with wooden chairs is positioned nearby. Natural light is introduced through a window, creating a bright and functional cooking space.

4.81 out of 5 average rating, 212 reviews

Bayside community, near OCMD, great rates

4.85 out of 5 average rating, 240 reviews

A wooded area features tall pine trees casting shadows on the soft ground covered with pine needles. In the background, the still water of a pond is visible, surrounded by foliage and gently reflecting the sky.

Home in Bethany Beach

Condo Villa 2B 2B, Walk 2 Beach Sl6

4.97 out of 5 average rating, 133 reviews

A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.

Home in Ocean City

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

A serene view of Sinepuxent Bay stretches across the horizon, showcasing expansive grasslands and soft green vegetation. The sky transitions to warm hues of sunset, creating a calming atmosphere. A glimpse of the fishing pier is visible in the distance, enhancing the waterfront scenery.

4.81 out of 5 average rating, 113 reviews

Mosaic Life Escapes -Bayfront Million Dollar Views

5 out of 5 average rating, 6 reviews

Mins to Golf & Ocean City! Sleeps 16 w. GameRoom!

4.99 out of 5 average rating, 101 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

Weekly house rentals

4.86 out of 5 average rating, 21 reviews

A living room area features a light-colored sofa and a red armchair, providing comfortable seating for guests. Light hardwood flooring and bright windows enhance the space, while a dark wooden table is positioned beside the sofa. A glimpse of the kitchen area can be seen through an open door.

Home in Onancock

A Little Serenity: Our Cozy One Bedroom Apartment

4.95 out of 5 average rating, 38 reviews

A two-story home from the early 1920s features a wraparound porch supported by white columns. Light-colored siding, red shutters, and a gently sloped lawn add to its charm. A sign is positioned in the front yard, and a slight overcast sky is visible in the background.

Home in Saxis

Island Voices In The Wine Near Chincoteague & NASA

Home in Deal Island Historic District

A bright dining area features a round table surrounded by wooden chairs. A colorful table runner adds a vibrant touch. Large sliding glass doors provide an unobstructed view of the water and open to an outdoor deck. A stylish chandelier hangs from the ceiling.

4.82 out of 5 average rating, 22 reviews

Reel Relaxation-Waterfront

5 out of 5 average rating, 11 reviews

A tranquil scene captures the houses situated near the marsh at sunset, with vibrant hues reflecting off the clouds. Lush grasses frame the foreground, leading to a wooden pathway connecting to the residences, surrounded by tall trees swaying gently in the evening breeze.

Home in Westover

5 bedroom waterfront retreat with private dock

Four light blue adirondack chairs are arranged beneath a tree adorned with string lights, creating a cozy seating area. A large, detached garage with a light-colored exterior is visible in the background, complemented by a grassy lawn illuminated by soft evening light.

4.98 out of 5 average rating, 88 reviews

Bikes-Kayaks-Outdoor Shower Grill-Firepit-Beach Eq

4.71 out of 5 average rating, 45 reviews

A two-story home with a gray exterior is showcased, featuring a distinctive pointed roof and a welcoming front porch. The porch is adorned with white railings. Gravel lines the front yard, bordered by wooden posts connected by rope. Nearby, a parked vehicle is visible.

Home in Greenbackville

Newly remodeled single-family house by the bay

An aerial view of a two-story duplex is presented, showcasing a well-maintained exterior with white siding and a sloped roof. The spacious lawn is bordered by a white picket fence, and a small shed is visible to the side. A black vehicle is parked nearby, surrounded by lush greenery.

4.88 out of 5 average rating, 24 reviews

Coastal Charm Duplex with Views of Horse Farm

A charming coastal cottage is viewed under a colorful sky at dusk. The inviting front porch is illuminated and features seating. A gravel driveway leads to the entrance, surrounded by a tranquil natural setting of trees and landscaping.

5 out of 5 average rating, 14 reviews

Coastal-Chic w/Private Backyard and Great Location

Private house rentals

A cozy fire pit area is surrounded by four Adirondack chairs, two in blue and two in turquoise. The setting includes a picturesque tidal pond with lush grass and reeds in the background, reflecting a serene atmosphere under a cloudy sky.

4.95 out of 5 average rating, 19 reviews

Beachgrass Bungalow

5 out of 5 average rating, 26 reviews

An elevated beach house stands gracefully by the canal, with a spacious upper deck visible under a colorful twilight sky. Lush trees frame the property, while a wooden dock provides direct access to the water, creating a serene and inviting coastal atmosphere.

Home in Ocean View

Cozy Stylish Waterfront 3BR Kayaks Fireplace Porch

A two-story cottage is presented with a light gray exterior and a white picket fence. A balcony extends from the second floor, offering blue accents. The front yard features greenery and flowering plants, while the clear blue sky adds to the home’s serene ambiance.

4.89 out of 5 average rating, 66 reviews

Oysterhaven Cottage-Waterview-Balcony

A spacious living area features a large sectional couch and a coffee table, surrounded by wooden flooring. A world map adorns the wall, and natural light streams in through the windows. The open layout flows into a dining area visible in the background.

5 out of 5 average rating, 37 reviews

Magnolia House ~Linens Included~

The inviting exterior of the cottage is framed by lush greenery, featuring a charming front door and welcoming pathway. A bicycle leans against the railing, while vibrant flowers and decorative landscaping enhance the coastal appeal. Natural light brightens the front of the house.

5 out of 5 average rating, 32 reviews

The Cottage Bluefish -new in '25

The living area features a spacious seating arrangement, including a dark sofa and cozy blue chair. Natural light is welcomed through large windows, while a wooden coffee table adds an organic touch. A Smart TV and decorative artwork enhance the inviting ambiance, leading to the dining area.

4.86 out of 5 average rating, 64 reviews

Chincoteague Island House "Sir Whelk-A-Lot"

A modern cottage exterior features a combination of brick and wood siding, highlighted by an inviting orange front door. Two garage doors flank the entrance, with a landscaped front yard adorned with shrubs and grass. Soft lighting enhances the home's contemporary design during dusk.

5 out of 5 average rating, 3 reviews

The Cottage @ Assateague Oasis.

The elegant waterfront home features a welcoming exterior with multiple levels and balconies. American flags adorn the front, while flowerbeds with greenery and stone pathways enhance the appeal. A smooth drive leads to the entrance, complemented by a tranquil waterside setting.