Vacation 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, 335 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!

4.94 out of 5 average rating, 127 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, 510 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, 174 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

4.85 out of 5 average rating, 111 reviews

The exterior of Ivy's Cottage showcases a charming gray shingle facade with a welcoming purple front door. A set of steps leads to a spacious porch, which is accompanied by white railings and decorative plants, enhancing the inviting entryway.

Cottage in Chincoteague

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

Just a few miles from the Chincoteague National Wildlife Refuge & Assateague Beach. Ivy's Cottage offers a great in-town location that's close to shops, restaurants, waterfront park, & public fishing pier. This beautifully renovated, this Chincoteague Island Cottage Features: Lovely eat in kitchen, fully equipped w/ all amenities. Cozy living room w/ full sleeper sofa & recliner. Queen bedroom w/ adjacent full bathroom. Large front porch perfect for outdoor dining & park style charcoal grill!

4.95 out of 5 average rating, 138 reviews

A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.

Cottage in Hacksneck

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

4.99 out of 5 average rating, 292 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!

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, 103 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 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.

4.99 out of 5 average rating, 238 reviews

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

LAST MINUTE OPENING-09-27 to 10-03-25 !!!! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

4.98 out of 5 average rating, 111 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.

4.97 out of 5 average rating, 618 reviews

The charming carriage house features a light-colored exterior with white trim and a metal roof. Two garage doors and multiple windows offer ample natural light, while a gravel driveway provides access to the entrance. Surrounding trees add a touch of greenery to the serene setting.

Guest suite in Berlin

Ayers Creek Carriage House

Our beautiful carriage house is located on 5 pristine acres along, scenic Ayers Creek, offering year round beauty. Only minutes from Assateague Island, Berlin, and Ocean City. Serene with abundant wildlife. Ideal oasis for outdoor enthusiasts. Worcester County Maryland Rental License #1324

Popular amenities for Chincoteague vacation rentals

Laptop-friendly workspace

Chincoteague beach vacation rentals

4.88 out of 5 average rating, 228 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❤️

4.94 out of 5 average rating, 176 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!

4.94 out of 5 average rating, 122 reviews

The serene outdoor view captures a vibrant sunset over the water, framed by two waterfront pavilions. Silhouetted trees stand on either side, while the grassy expanse leads down to the beach, creating a peaceful atmosphere for relaxation.

Home in White Stone

Coastal Farmhouse Getaway

4.97 out of 5 average rating, 103 reviews

A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.

Condo in Ocean City

Gorgeous New Beachfront! King Bed, Direct Sea View

4.99 out of 5 average rating, 150 reviews

A private balcony features a high table with two chairs, providing an unobstructed view of the ocean and beach below. The scene is enhanced by the bright blue sky and gentle waves, creating an inviting spot for enjoying morning coffee.

Condo in Ocean City

Beautiful Renovated Ocean Front Condo 1b/1.5ba

Guest suite in Fenwick Island

A cozy guest suite is presented, featuring a spacious bed covered with a vibrant blue blanket. Decorative elements include a light-colored rug and a plant next to the bed. A small bookshelf and artwork adorn the walls, contributing to the room's inviting decor.

4.8 out of 5 average rating, 112 reviews

Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!

4.87 out of 5 average rating, 197 reviews

A vibrant display of the northern lights illuminates the night sky with shades of red and green, reflecting softly on the water's surface. The silhouette of a sailboat is visible, along with a shore that includes trees and lighted structures.

Apartment in Exmore

Private Entrance Apartment on the Chesapeake

4.95 out of 5 average rating, 295 reviews

The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.

Condo in Ocean City

Direct Oceanfront with a View and Amenities Galore

Chincoteague house rentals

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, 35 reviews

Magnolia House ~Available This Week~

4.99 out of 5 average rating, 133 reviews

A charming house with large windows is situated by the water, framed by lush greenery. A wooden dock leads from the house to the water's edge, surrounded by tall grass. Soft evening light highlights the structure, creating a serene ambiance.

Home in Ocean Pines

Charming Waterfront Cottage w/2 King Suites + Dock

4.98 out of 5 average rating, 118 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

4.95 out of 5 average rating, 253 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

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

A charming two-story cottage is displayed, featuring bright blue siding. The front appears framed by white trim around the windows, which are adorned with window boxes. A concrete path leads to the front door, and a fenced area can be seen in the background.

4.78 out of 5 average rating, 51 reviews

Waterman's Reel

A two-story waterfront home is visible, elevated on stilts with a spacious deck featuring steps leading down to a private dock. Brightly colored kayaks are stored on the dock, and lush trees surround the property, providing a natural, serene backdrop.

4.95 out of 5 average rating, 42 reviews

Jay's Retreat

A charming two-story building is presented in a row of identical homes, featuring light gray siding and white accents. Each unit has a front door, with some balconies visible above. Lush green grass is maintained in the front yard, framed by colorful landscaping.

4.99 out of 5 average rating, 91 reviews

Central Location-Walk 2 Dining-Recently Renovated!

Private Chincoteague vacation rentals

4.67 out of 5 average rating, 295 reviews

A sleek building is situated by the water's edge, reflecting the soft hues of a sunset. Clouds scatter across the sky, casting gentle shadows, while pilings extend from the shore into the tranquil bay. The serene scene invites relaxation and appreciation of the natural beauty.

Condo in Chincoteague

Le Petit Paradis-Waterfront, pet-friendly Studio

5 out of 5 average rating, 54 reviews

An aerial view of Crooked Elm Cottage is presented, showcasing a cozy cottage with a steeply pitched roof nestled among lush green fields. Surrounding trees and open spaces complement the serene rural setting, with a dirt driveway leading up to the charming retreat.

Cabin in Westover

Chalet Style Home, private country setting

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 modern kitchen featuring a large island with four wooden bar stools. White cabinets, stainless steel appliances, and a minimalist design create an organized space. Natural light illuminates the room through a nearby window, enhancing the inviting atmosphere.

5 out of 5 average rating, 11 reviews

Chincoteague Cottage

4.97 out of 5 average rating, 39 reviews

The exterior of a charming white cottage is showcased, featuring two sets of stairs leading to the front porch. The well-maintained lawn is punctuated by a small garden area, and a decorative figure can be seen near the entrance.

Cottage in Chincoteague

Waterfowl Watch Chincoteague Buy 2 nights get 1!

4.93 out of 5 average rating, 70 reviews

A gravel driveway leads towards a rustic boathouse with weathered wooden siding, framed by tall grasses and marshland. The iconic Chincoteague lighthouse can be seen in the distance, completing the scenic view under a clear sky.

Cabin in Chincoteague

The Boathouse: Charming & Historic Waterfront Stay

4.97 out of 5 average rating, 29 reviews

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon