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Cottage vacation rentals in Assateague Island

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Top-rated cottage rentals in Assateague Island

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Guest favourite
A single-story home sits nestled among lush greenery, featuring a welcoming front porch with a wooden railing. A set of steps leads up to the entrance, flanked by large windows adorned with green shutters, complementing the home's neutral exterior.
Cottage in Ocean Pines

Cozy Beach Getaway in the Lovely Ocean Pines North

Welcome to our Cozy Beach Getaway!! ☀️🌊👙⛱️🐚🏖️🌞🌅⛅️ This beautiful and peaceful home is located in Ocean Pines North. 3 bedrooms, 2 bathrooms. Peaceful front porch and back deck. 🏡🏝️ Whether you’re looking for a summer family vacation, girls weekend getaway, or just a break from reality, this is the perfect place! Washer/dryer 🧺, two smart TV’s 📺, driveway fits 4 cars comfortably 🚗. Enjoy the hustling city of Ocean City during the day and stay in the tranquility and peaceful Ocean Pines at night! 🏖️💞☀️

FamilyValueLayout

4.9 out of 5 average rating, 216 reviews
Top guest favourite
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.
Cottage in Chincoteague

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!🐴🦪🌅

ValueFamilyKitchen

4.94 out of 5 average rating, 215 reviews
Top guest favourite
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.

FamilyLocationLong stay

4.98 out of 5 average rating, 163 reviews
Top guest favourite
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.
Cottage in Chincoteague

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.

LocationFamilyLayout

4.96 out of 5 average rating, 170 reviews
Guest favourite
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!

LocationValueCheckout

4.95 out of 5 average rating, 167 reviews
Superhost
Cottage in Chincoteague

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!

ValueFamilyBeach

4.86 out of 5 average rating, 121 reviews
Guest favourite
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!

FamilyLocationBreakfast

4.94 out of 5 average rating, 191 reviews
Top guest favourite
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

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

LocationFamilyAmenities

5.0 out of 5 average rating, 261 reviews
Guest favourite
Tall grasses sway gently in the foreground, framing a serene body of water. The calm surface reflects a clear blue sky, while a distant shoreline is visible along the horizon. The scene captures a tranquil natural setting by the water's edge.
Cottage in Saxis

ISLAND SUNSETS Near Chincoteague Island

1 - Story Near Chincoteague Island Virginia Assateague Beach NASA Wallops Island, Va. Onancock, Va Waterman’s Fishing Village Surrounded by Water on three sides & Virginia Wildlife Refuge on fourth side. 400 ft. Walking distance to Beach, Kayaking & Canoeing, Wildlife, Fishing Pier, Boat Ramp, Marina, Public Pavilion, 2 Restaurants, Museum, Multiple Seafood Shantys

ValueLocationParks

4.87 out of 5 average rating, 235 reviews
Top guest favourite
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. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

FamilyLocationHospitality

4.99 out of 5 average rating, 268 reviews
Top guest favourite
The exterior of the cottage is shown, featuring a welcoming entryway with stairs and a blue door. Two blue adirondack chairs are positioned on the well-maintained lawn, with a glimpse of the waterfront visible through large windows. Surrounding greenery enhances the outdoor setting.
Cottage in Smith Island

Levering Creek Cottage with private dock

Levering Creek Cottage is a waterfront property with a deep water dock that you can see from the back door. We are located on Levering Creek where you can sit on the dock watching watermen arrive with their daily catch, see nesting bald eagles, watch beautiful sunrise, fish and crab. We are also just steps away from most everything including the ferry.

LocationFamilyHeating

4.97 out of 5 average rating, 278 reviews
Top guest favourite
Cottage in Berlin

Bayfront Cottage w/ Amazing Views

Whether you’re enjoying time by the firepit or sipping coffee on the couch, the views of Sinepuxent Bay and Assateague Island make this cottage the ideal spot for your next vacation. The cottage is located in a quiet neighborhood and is only a short drive from Assateague Island, the historic town of Berlin, and the Ocean City Boardwalk.

FamilyLocationAccess

4.98 out of 5 average rating, 223 reviews

Popular amenities for Assateague Island cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top guest favourite
The open living space features light wooden paneling and natural light streaming through multiple windows. A blue sofa faces a flat-screen TV, while a small dining table with stools is positioned nearby. The kitchen area is equipped with modern appliances for convenience.
Cottage in Dewey Beach

Uncle Buck's Cottage

FamilyValueAccess

4.91 out of 5 average rating, 109 reviews
Top guest favourite
A cozy sleeping area features a soft blue quilt covering the spacious bed, adorned with colorful dog-themed pillows. A neatly folded stack of white towels rests on the bed, while a bedside lamp provides gentle lighting, enhancing the room's warm ambiance.
Cottage in Rehoboth Beach

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

FamilyValueCheckout

4.96 out of 5 average rating, 226 reviews
Guest favourite
An aerial view depicts a private above-ground pool surrounded by a spacious wooden deck. Multiple seating areas with umbrellas offer shade, and lush greenery borders the property, adding a natural ambiance. The outdoor kitchen and grill area are visible, enhancing the deck's recreational space.
Cottage in Marion Station

Pool/HotTub/RecRoom/Pvt. Dock YearRoundPlayground

FamilyLocationQuiet

4.81 out of 5 average rating, 59 reviews
Top guest favourite
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

ValueLocationKitchen

4.9 out of 5 average rating, 78 reviews
Top guest favourite
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

Hot Tub Haven 2 Mi to Beach! ‘Christy's Cottage’

ValueFamilySleep quality

4.98 out of 5 average rating, 85 reviews
Guest favourite
Cottage in Frankford

Outdoorsy Cottage, Pet Friendly, Hot Tub & FirePit

LocationHot tubCheck-in

5.0 out of 5 average rating, 9 reviewsThe 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

Cropper Creek House

LocationFamilySleep quality

4.89 out of 5 average rating, 54 reviews
Guest favourite
Cottage in Ocean View

25 % off: Bethany Bay | Beach+Hot Tub+Pool+Views

FamilyLocationView

5.0 out of 5 average rating, 7 reviews

Pet-friendly cottage rentals

Guest favourite
The exterior of a two-story cottage is shown, featuring a blue metal roof and white siding. Blue shutters frame the windows. A small deck is visible in front, furnished with two adirondack chairs in bright green. A door centrally accesses the home.
Cottage in Wingate

Blue Crab Cottage: Remote+Nature+Fishing+Views

ValueFamilyParking

4.84 out of 5 average rating, 103 reviews
Guest favourite
An inviting entrance features a bright white door adorned with a decorative wreath. Lush white hydrangea flowers bloom vibrantly in the foreground, complementing the blue exterior of the cottage.
Cottage in Lewes

BnB’s Dog-Friendly Garden Cottage

LocationValueAmenities

4.86 out of 5 average rating, 227 reviews
Guest favourite
Cottage in Lewes

Dog-Friendly Retreat with Fenced Yard, Fire Pit

ValueFamilyWalkability

4.93 out of 5 average rating, 138 reviews
Guest favourite
A cozy living area is highlighted by a yellow armchair and a white accent chair. A small table with a blue lamp stands beside them. Natural light filters through the partially covered windows, and a television is mounted on the wall opposite the seating.
Cottage in Rehoboth Beach

Cozy Cottage Close to Downtown Built in 2021

LocationFamilyKitchen

4.95 out of 5 average rating, 130 reviews
Top guest favourite
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

ValueFamilyBathroom

4.97 out of 5 average rating, 126 reviews
Top guest favourite
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

FamilyLocationGetting around

4.99 out of 5 average rating, 89 reviews
Top guest favourite
Cottage in Galestown

Cozy Millpond Cottage • Fall Getaway

LocationValueQuiet

4.96 out of 5 average rating, 25 reviews
Top guest favourite
Cottage in Melfa

Waterfront 1BR on Working Farm w/ Deck + View

LocationCleanlinessQuiet

4.92 out of 5 average rating, 48 reviews

Private cottage rentals

Top guest favourite
A tranquil garden path leads to the cottage entrance, flanked by lush greenery and vibrant flowers. A small fountain gently flows, surrounded by well-manicured grass and white gravel. The serene ambience is highlighted by the dappled sunlight filtering through the leaves.
Cottage in Lewes

Charming, Historic Lewes Cottage

FamilyLocationBathroom

4.97 out of 5 average rating, 316 reviews
Top guest favourite
The exterior of a charming cottage is surrounded by green grass and trees. The wooden shingle siding complements the white trim around the windows and doors. A pathway leads to the entrance, and an American flag is displayed on the front porch, hinting at a welcoming atmosphere.
Cottage in Ocean View

Basil Cottage at Good Earth, near Bethany Beach

ValueLocationCondition

4.92 out of 5 average rating, 299 reviews
Top guest favourite
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

ValueLocationIndoor spaces

4.95 out of 5 average rating, 262 reviews
Top guest favourite
A charming single-story home is presented with a welcoming front porch. Flanked by lush green trees, the residence features a neatly manicured lawn and a driveway that leads to an attached garage, providing a serene and inviting outdoor setting.
Cottage in Selbyville

The Cove Cottage, West Fenwick

FamilyLocationDecor

4.97 out of 5 average rating, 101 reviews
Top guest favourite
The exterior of a charming cottage is depicted, featuring a white wooden facade and a metal roof. A small stone patio with a bistro table and chairs sits at the entrance, surrounded by lush greenery and flowering plants. Two windows invite natural light into the space.
Cottage in Onancock

Little Cottage on the Creek

LocationRiverView

4.96 out of 5 average rating, 136 reviews
Guest favourite
A charming beach cottage in a vibrant blue hue is framed by a black gate and a wooden fence. Lush greenery and blooming azalea bushes add color to the entrance, leading to a pathway illuminated by natural light. A gentle slope of trees enhances the tranquil setting.
Cottage in Dewey Beach

Shady Shore Cottage in North Dewey Beach

FamilyLocationLaundry

4.92 out of 5 average rating, 122 reviews
Top guest favourite
A comfortable living area is highlighted by a sectional sofa with neutral tones. A round dining table for four is set next to large windows, inviting natural light. Artwork depicting coastal scenes decorates the walls, enhancing the home's airy ambiance.
Cottage in Lewes

Hetty's House - Your Cozy Retreat

ValueFamilyCleanliness

5.0 out of 5 average rating, 115 reviews
Guest favourite
A serene landscape captures the sun setting over the water, casting warm hues across the sky. The water reflects the colors, with gentle waves lapping at the sandy shore. Silhouetted trees line the horizon, creating a peaceful backdrop.
Cottage in Tyaskin

Charming Cottage in Tyaskin, MD

FamilyLocationHeating

4.85 out of 5 average rating, 126 reviews