Cottage holiday rentals in Chincoteague

The vintage cottage features a charming façade with light blue siding and a gabled roof. A welcoming entryway is framed by shrubs and decorative pumpkins, while large windows invite natural light. Steps lead to a front porch with a cozy seating area.

4.94 out of 5 average rating, 188 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!🐴🦪🌅

The exterior of a two-story cottage is displayed, featuring a welcoming porch with rocking chairs. Surrounded by tall trees, the structure showcases a combination of wood and stone elements, along with multiple windows allowing natural light to flood in.

4.9 out of 5 average rating, 159 reviews

Pony Pines!Your Waterfront Getaway Cottage Awaits!

Imagine a quiet retreat on the water where the sunsets are magnificent, and wildlife such as geese, raccoons, deer, owls, and egrits are to be experience in the backyard. Pony Pines offers a firepit, a master bedroom with a jacuzzi tub, and a clawfoot tub on the main floor. We have 2 Kayaks for your use on the canal, and a storage shed with some of the beach accessories you may need for your days at the Ocean. Linens are provided! Relax with your whole family at this peaceful, Happy Place.

4.95 out of 5 average rating, 253 reviews

The exterior of Westview Cottage is shown, featuring a well-maintained lawn with lush greenery. Floor-to-ceiling glass doors are visible, reflecting the surrounding landscape and allowing natural light into the cottage. Trees and shrubs frame the view, enhancing the serene atmosphere.

Cottage in Onancock

Eastern Shore Romantic Waterfront Getaway Upscale

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

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, 157 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.

4.98 out of 5 average rating, 145 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 LLC - quiet and peaceful

Cozy cottage located on a quiet backroad overlooking a wide open field & back deck provides warm & sunny space for relaxing or reading a book. The kitchen is fully equipped. BFC has a warm farm house feel w/ a touch of the beach. The bathroom has been updated to a more modern feel. Located only a few miles from both seaside and bayside boat ramps. A 7 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wallops & Chincoteague are just a short drive.

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.

4.85 out of 5 average rating, 111 reviews

"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, 139 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!

4.94 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!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

4.99 out of 5 average rating, 191 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 Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. 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 serene waterfront view captures a calm body of water reflecting a colorful sunset. Silhouettes of grass line the shore, while a long pier extends into the distance, adding depth to the tranquil scene.

4.95 out of 5 average rating, 177 reviews

Summer's Sea Shanty on Chincoteague Island

Summer's Sea Shanty is a delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups of friends. We've worked hard to make this the ideal modern day beach retreat. This home boasts screened in front and back porches, a fire pit, an open/functional floor plan. We're pet and kid friendly with luxury linens and rugs and dish ware... We're proud to be the best of the best on the island. We're centrally located and minutes from Assateague National Seashore.

4.83 out of 5 average rating, 275 reviews

A charming beach cottage is displayed in an A-frame design, featuring a large front porch with white railings. Windows are covered by striped awnings, allowing natural light to filter in. The landscaped yard includes low shrubbery, adding to the inviting exterior.

Cottage in Bethany Beach

A-mazing Beach Cottage on Canal & Trolley Route

Welcome to our beach house! An "A"dorable cottage located on Bethany Canal, an easy walk, bike ride, or trolley to the Boardwalk and BEACH! Perfect for families (comfortably sleeps 4 adults and plus children), and small groups of friends alike! 3 bedrooms, 1 full bathroom, plus an enclosed outdoor shower. Very clean, tons of natural light, and plenty of outdoor space -- including a relaxing and bright sunroom/porch, small deck out back with a grill, and large front porch.

4.99 out of 5 average rating, 240 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

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.

Popular amenities for Chincoteague cottage rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

The front exterior of the creek house is shown, featuring a welcoming porch with steps leading up. A colorful flag waves gently, and vibrant greenery surrounds the area, while a white railing offers a pleasant border. The house has a light beige facade complemented by green accents.

Cottage in Newark

4.89 out of 5 average rating, 54 reviews

Cropper Creek House

A view of an outdoor area featuring a waving American flag illuminated by soft string lights. The scene includes a backdrop of lush green grass and trees, with a serene canal reflecting the evening sky's colors.

Cottage in Bethany Beach

4.82 out of 5 average rating, 22 reviews

Bethany Beach Sea Colony Canalside Sleeps 7

5 out of 5 average rating, 80 reviews

A serene water view is captured as the sun sets, casting warm hues of orange and pink across the sky. The calm surface of the water reflects the colorful clouds, while a pier extends into the scene, inviting leisure and tranquility.

Cottage in Woolford

Waterfront Cottage & Guesthouse Near Cambridge

Cottage in Marion Station

An aerial view showcases a rustic-modern house surrounded by greenery. Red pathways lead to the entrance, and a wooden deck is visible with steps leading up to the front door. In the background, a private pool and shaded seating areas offer outdoor relaxation options.

4.77 out of 5 average rating, 48 reviews

Year Round Playground - Rare Rustic-Modern Getaway

4.93 out of 5 average rating, 14 reviews

A dining area features a wooden table surrounded by comfortable chairs upholstered in light fabric. Colorful abstract artwork adorns the wall above. A television is mounted nearby, while patio doors lead to a deck area, allowing natural light to fill the space.

Cottage in Bethany Beach

2br | 2 bath. tennis, pool, hot tub, 0.5m to beach

4.9 out of 5 average rating, 52 reviews

The cottage exterior features a welcoming design with a red front door, surrounded by a gravel pathway and lush greenery. Large windows brighten the facade, while a porch with railings offers a relaxing space to enjoy nature.

Cottage in Selbyville

"Bayside" Coastal Cottage w/ Golf, Hot Tub + EV

4.97 out of 5 average rating, 58 reviews

The exterior of a blue cottage is shown, featuring a sloped roof and a welcoming front porch with seating. Lush green grass surrounds the home, and a large area of trees is visible in the background, providing a natural setting.

Cottage in Snow Hill

‘Christy's Cottage’ w/ Hot Tub - 2 Mi to Beach!

Pet-friendly cottage rentals

Superhost

Two wooden Adirondack chairs are positioned on a weathered dock, facing towards a calm waterway. A shaded structure is visible on the left, while boats are anchored in the distance against a backdrop of blue skies dotted with white clouds.

4.73 out of 5 average rating, 110 reviews

SNUG HARBOR waterfront cottage with a grand view!

4.98 out of 5 average rating, 61 reviews

The exterior of the cottage is displayed, featuring a welcoming front porch with seating. Lush greenery surrounds the home, and a gravel pathway leads to the entrance. Large windows allow natural light, and a decorative plant is positioned near the entrance.

Cottage in Ocean Pines

3-bedroom cottage in Ocean Pines

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, 31 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

4.91 out of 5 average rating, 55 reviews

A serene view of the Chesapeake Bay stretches across the horizon, reflecting sunlight on the calm water. The beach area, featuring soft sand and gentle waves, leads up to trees dotting the shoreline. The cottage is nestled amidst the natural landscape.

Cottage in Reedville

Waterfront Bay Cottage w/ Your Own Private Beach

4.97 out of 5 average rating, 103 reviews

A cottage is set within a private wooded yard, surrounded by lush greenery. The exterior features white siding and black shutters. A grassy area leads to a wooden porch with steps, while a seating area is visible in the garden, offering a peaceful retreat.

Cottage in Cambridge

Cambridge Cottage

4.93 out of 5 average rating, 152 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

4.8 out of 5 average rating, 15 reviews

A light-filled living area showcases a navy sofa facing a mounted television. A striped ottoman sits on a woven rug, while a plant adds a touch of greenery. Dining chairs and natural light from surrounding windows create an inviting space for relaxation.

Cottage in Ocean City

Bungalow 611

Private cottage rentals

4.94 out of 5 average rating, 51 reviews

The exterior of a charming blue cottage is surrounded by lush greenery and vibrant pink flowers. A spacious front porch is visible, complete with white railings. The entrance features an arched window above the door, creating an inviting entrance that blends with the natural surroundings.

Cottage in Ocean Pines

Rhapsody in Blue Beach Cottage Ocean Pines, OC MD

4.95 out of 5 average rating, 19 reviews

A welcoming entrance is framed by neatly trimmed hedges and a well-maintained grassy area. The front porch features decorative railings and steps leading up to a door with a wreath. An American flag is displayed, adding to the home's charm.

Cottage in Onancock

ESVA Down by the Sea & Pet Friendly

Superhost

A welcoming entrance features a blue exterior with white trim and an American flag displayed. Two chairs sit on the wooden steps, accompanied by colorful flower beds and decorative lanterns. The peaceful surroundings are enhanced by additional small flags placed nearby.

Cottage in Frankford

5 out of 5 average rating, 4 reviews

5 Miles to Beach Quiet Secluded 3 Bedroom Cottage

4.83 out of 5 average rating, 69 reviews

The exterior of a charming beach bungalow is seen, featuring a light grey facade and a welcoming front porch with a screened-in area. Colorful flowers are planted along the walkway, and lush greenery surrounds the property, creating a serene outdoor setting.

Cottage in Ocean View

OV Central Beach Cottage

4.98 out of 5 average rating, 49 reviews

A classic two-story house is showcased, featuring white siding and contrasting black shutters. A vibrant red door serves as a focal point. The front steps are flanked by neatly trimmed shrubs, and a green lawn extends to the sidewalk, providing an inviting entrance.

Cottage in Cambridge

Cozy 3-bedroom cottage steps away from the water.

5 out of 5 average rating, 57 reviews

Cottage in Smith Island

IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental

Superhost

An inviting living area features a blend of furnishings, including a dark sectional sofa with decorative cushions and an orange chair. Natural light filters through the windows, illuminating the textured ceiling and light wood flooring. A central coffee table is accompanied by minimal decorative accessories.

Cottage in Ocean City

4.63 out of 5 average rating, 68 reviews

Newly Renovated with free parking on premises