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Assateague Island vacation rentals

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Top-rated vacation rentals in Assateague Island

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

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Colorful armchairs with a fish pattern provide comfortable seating by large windows that offer views of the water and surrounding nature. A small green side table stands between the chairs, adorned with a vase of flowers.

Home

4.78 out of 5 average rating, 23 reviews

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

Home

5 out of 5 average rating, 39 reviews

Chic Coastal Retreat: Steps to Beach Road & Dining

Experience the ultimate in coastal living at this beautifully renovated home, a stone's throw from the Beach road. Seasonal discounts available, this is your perfect getaway destination. The interior features 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 and balcony for serene morning views 🌄

A charming cottage is framed by vibrant gardens filled with colorful flowers, including yellow daffodils and purple tulips. A stone pathway leads to the welcoming porch, where rockers invite relaxation. Green foliage and trees enhance the peaceful setting, offering a serene atmosphere.

Cottage

4.9 out of 5 average rating, 109 reviews

Dog friendly, Close to outlets, fire pit, Sleeps 6

Tucked away in a quiet neighborhood, this adorable cottage awaits your next peaceful vacation. With 3 beds/2 baths, there’s space to enjoy a relaxing stay for up to 6 guests with cozy blankets and beds as well as beautiful surrounding gardens. We are only 4 miles to the beaches, 1 mile to outlet shopping, and close to amazing restaurants. You may not even want to leave the cottage at all. Pet friendly (1 dog please). NEW FOR 2024: beautiful bathroom updates and NEW comfy mattress in the master!

An aerial view of the midtown area showcases several multi-story buildings, with the ocean visible in the background. The coastline is framed by sandy beaches, and a parking area is seen adjacent to the structures, creating a vibrant beachside scene.

Condo

4.95 out of 5 average rating, 168 reviews

Modern Oceanside 42nd st 2bed 2bath sleeper sofa

Gorgeous 2 bed, 2 bath 1st floor condo is on 42nd st. Ocean side! Newly renovated, modern and clean condo sleeps 8 (air mattress for 2)has everything you need to feel like you’re at home away from home! Beautifully decorated and complete with stainless steel appliances, fully equipped kitchen, WiFi, a color changing gas fireplace, 80” tv, and is furnished with linens and towels. Just steps to the beach, convention canter and walking distance to the bars such as Seacrets, Coconuts and Taphouse.

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.

Home

4.87 out of 5 average rating, 106 reviews

Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

LOCATION, LOCATION, LOCATION!!! Located in the heart of Chincoteague, Sunny Claire is just steps away from downtown restaurants, shopping, theater, town park, fishing pier & carnival grounds. Relax in the hot tub, read a book or enjoy sunsets from one of the cozy porches, or just stroll along Historic South Main Street. This well appointed cottage offers the perfect vacation spot for your Chincoteague vacation. Sleeps 8 Master w/ King Sleep Number Bed Bedroom #2 (1 Q) Bedroom #3( 1 Q, 1 F)

A serene lake view features gentle fountains spraying water, surrounded by well-maintained greenery. Various residential buildings with sloped roofs stand along the water's edge, framed by lush trees and a clear blue sky.

Townhouse

4.93 out of 5 average rating, 109 reviews

Lakefront slps 6; beach, pools, tennis, gym, view!

Lake front in Sea Colony Resort! Walk to beach, pools, tennis/pickleball, putting green, bocce, shuffleboard, fishing ponds, fitness center & more! 24/7 security. Completely renovated. Well equipped kitchen opens to bright, charming living/dining rooms with seating for six. AC, charcoal grill, washer/dryer, wifi, 3 flat screen TV's & 3 queen beds. Beach tram & pool across street. Large deck with great view of lake and fireplace in living room! Professionally cleaned between guests.

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.

Home

4.9 out of 5 average rating, 111 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!

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage

5 out of 5 average rating, 101 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

A spacious bedroom features a large bed with a patterned comforter and multiple decorative pillows. Natural light floods the room through a glass door leading to a balcony. A bedside table with a lamp and a potted plant add to the calming atmosphere.

Condo

4.93 out of 5 average rating, 102 reviews

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

A cozy seating area features a light-colored couch adorned with decorative pillows. A woven coffee table rests on a natural fiber rug, while a window nook is lined with plants, allowing natural light to brighten the space. Wooden accents add a warm touch.

Tiny home

4.83 out of 5 average rating, 120 reviews

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

Condo

5 out of 5 average rating, 17 reviews

The Tarryn Elizabeth Unit A

What better way to enjoy a getaway or family vacation than on a peaceful quiet island where the beach is clean and spacious and some of best fishing and crabbing in the world! Rent a four wheeler and drive on the beach 24/7 or lounge on the porch and soak in the sun, and not to mention the unlimited hi speed Internet with smart TVs in all 3 rooms for all your relaxing needs if you should choose to stay in the home!

The kitchen features modern appliances and a spacious island with seating for three. Natural light enters through a skylight and glass door, illuminating the light-colored cabinetry and countertops. A hallway leading to other areas of the house is visible in the background.

Home

4.96 out of 5 average rating, 130 reviews

Woodsey Beach House - Beach, Lake, Woods!

Beach? Check Cabin? Check Lake? Check Have it all at our home near the beach, in a beautiful wooded setting with a lake view! Quiet neighborhood makes you feel right at home. Newly renovated with new appliances and furnishings. The house has an upside-down layout, so most of the living spaces, including the kitchen, dining, and living rooms are on the second floor. The home is unique, bright and comfortable.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Assateague Island vacation rentals

Free parking on premises

Assateague Island beach vacation rentals

A covered patio offers a spacious table with four chairs, situated above sandy terrain leading to the beach. Beach grass and low vegetation are visible in the distance, while clouds drift across the sky, framing a serene coastal scene.

Townhouse

4.98 out of 5 average rating, 42 reviews

Unique Direct Oceanfront 3-Level w/a Private Beach

Condo

4.9 out of 5 average rating, 77 reviews

COZY 3BR BEACH LOFT - pool/tennis court

A sandy pathway leads to a tranquil beach, bordered by wooden posts and a low fence. The calm ocean glistens in the sunlight, and a clear blue sky stretches overhead, creating an inviting scene for leisurely walks by the water.

Condo

4.95 out of 5 average rating, 19 reviews

Beach Bliss - A Modern Ocean City Rental

A view of the ocean and sandy beach is presented from a balcony. Nearby buildings feature rooftops in varying shades of blue, while a beach boardwalk and recreational equipment are visible along the shoreline. The expanse of water stretches toward the horizon under a light haze.

Condo

4.85 out of 5 average rating, 13 reviews

Experience a Seashore Adventure! Book today!

The exterior of a retro beach cottage showcases a vibrant turquoise facade. Soft lighting highlights the entrance and decorative signage. A well-maintained lawn with landscaped shrubs complements the inviting appearance. Adjacent buildings offer a glimpse of the bustling surroundings.

Cottage

4.85 out of 5 average rating, 27 reviews

Sandy Sheets cozy beach cottage

A sandy path leads to the beach, bordered by wooden fencing. Sparse grass grows on either side, and a sign indicating rules is prominently placed near the sand. The ocean stretches in the background under a clear blue sky.

Condo

4.85 out of 5 average rating, 55 reviews

Ful Dek - Family Casual Condo-Midtown-Ocean Block!

An outdoor dining area is shown, featuring a light blue picnic table surrounded by four matching chairs. A patio umbrella stands upright in the center, offering shade. A tall tree is visible in the background along with a white fence that encloses the space.

Villa

4.93 out of 5 average rating, 29 reviews

Cheery & Cozy Beach Villa - Walk to Beach

A covered balcony features comfortable seating with soft cushions, overlooking the beach and ocean. The railing is white, and potted flowers add a touch of greenery. The vibrant beach can be seen in the distance, with people enjoying the sand and waves.

Apartment

5 out of 5 average rating, 6 reviews

Luxury Beach Front Vista on the OCMD Boardwalk

Assateague Island house rentals

A quaint two-story house is surrounded by lush greenery, featuring a well-maintained yard filled with blooming flowers. The exterior displays white siding with dark shutters, and steps lead up to a welcoming porch, enhancing the home's inviting character.

Home

4.78 out of 5 average rating, 130 reviews

BayTime

A bright living area features a plush blue sofa and a patterned chair, complemented by a sleek gas fireplace. Light filters through the window blinds, illuminating the space. A dining table is nearby, decorated with natural elements, enhancing the homey environment.

Home

4.94 out of 5 average rating, 211 reviews

Cozy Home at 109 Swedes St

Home

4.89 out of 5 average rating, 18 reviews

New 5 Bdrm/Bayside Home/Prime Spot/Private Parking

A single-story house is presented, featuring a welcoming front porch with screened seating. The exterior is surrounded by well-maintained grass and mature trees displaying autumn foliage. A driveway leads to the entry, enhancing the inviting appearance of the home.

Home

4.95 out of 5 average rating, 194 reviews

Pet friendly cottage 4 blocks to Beach

A dining area features a round wooden table surrounded by six chairs. A decorative plate with shells is centered on the table. Bright light enters through the glass doors leading to the screened porch, with a view of the outdoor space and surroundings.

Home

4.95 out of 5 average rating, 106 reviews

In-Town Rehoboth Beach, Walk to Everything!

A cozy living area features a light-colored sofa and a decorative ottoman on a patterned area rug. Large windows allow natural light to brighten the space, while a holiday-themed tree adds a touch of festivity. A dining area can be seen in the background.

Home

4.98 out of 5 average rating, 195 reviews

Beautiful Renovated Home, Perfect Getaway!

The exterior of the home features a light green facade with a bright red door. A stone pathway leads to the entrance, flanked by landscaped flower beds containing purple flowers. Trees and shrubs are visible in the background under a clear blue sky.

Home

4.82 out of 5 average rating, 172 reviews

IN-TOWN - WALK/BIKE/DRIVE TO BEACH/DINING & STORES

The image displays the exterior of a ranch-style house featuring a brick facade and white siding. Lush greenery surrounds the property, while a nearby historic house with a distinctive turret is visible across the street. A clear blue sky offers a bright backdrop.

Home

4.87 out of 5 average rating, 122 reviews

Hudson House

Assateague Island condo rentals

A living room features two sofas, one with stripes and the other with a floral pattern. A large area rug with a starfish design lies on the floor. Natural light enters through a window, illuminating the space where artwork is displayed on the walls.

Condo

5 out of 5 average rating, 11 reviews

Condo on the Canal 13th Street (Aronimink)

The image captures a serene view of the bay, with calm waters extending toward the horizon. A wooden pier can be seen jutting into the water, complemented by a nearby tree that adds a touch of greenery. The sky is partly cloudy, enhancing the natural setting.

Condo

4.91 out of 5 average rating, 273 reviews

Wight Bay Unit 245

Condo

4.98 out of 5 average rating, 113 reviews

Ahoy Condo! Great ocean view just steps to beach!

Condo

4.78 out of 5 average rating, 105 reviews

Spacious Direct Oceanfront 1BR Condo w/Balconies

A spacious living area features a comfortable gray sectional sofa adorned with colorful cushions. An inviting lamp sits on a coffee table, while the light beige walls complement the tiled flooring. The open layout connects to the kitchen and dining space in the background.

Condo

4.82 out of 5 average rating, 265 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

The exterior of the condo is displayed, featuring a three-story building with a tan façade and turquoise accents. Walkways with white railings lead to individual entries, while lush greenery borders the property. A sign identifying the condo is visible at the entrance.

Condo

4.93 out of 5 average rating, 44 reviews

2BR/2BA/ 5 Bed condo with 2 private balconies!

An open-concept living area features a light gray sofa with blue accent pillows, complemented by a white coffee table. A spacious kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light brightens the space, enhancing its modern design.

Condo

4.87 out of 5 average rating, 101 reviews

Charming Remodeled 2 level condo w/ amazing views

A light-filled living area features a cozy couch with decorative pillows, complemented by a small coffee table. A flat-screen TV is mounted on the wall opposite a comfortable seating arrangement, which includes a recliner and a wicker chair. Light gray curtains frame the window.

Condo

4.74 out of 5 average rating, 19 reviews

Mallard condo’s A

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