
Holiday rentals with outdoor seating in Assateague Island
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Assateague Island
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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.

Ocean City Townhome by Beach Bayside
If you're looking for a vacation home, consider this convenient duplex located just a few blocks from the beach. Situated on the second floor, this vacation rental offers all the necessary amenities for a comfortable stay with Food lion, Target and Marshalls nearby. Enjoy a short, seven-minute walk to Harpoon Hanna's, a local restaurant hotspot. For entertainment, Jolly Roger Amusement Park, James Farm Ecological Preserve, Roland Convention Center, host regular sports events and live shows.

Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!
Unwind and chill in this boho coastal inspired guest suite on the ocean side. At Sea Dunes' private guest king suite, the surf and sand are steps away. Get ready to pack your cooler and enjoy a day in the sun on this beautiful, private dog-friendly beach. Sea Dunes is located in Fenwick Island, DE and nestled between protected state nature parks. Just a short trip in the car to a marina with watersports, kayak adventures on the bay, local dining, farm markets and shopping.

Beachfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with a breathtaking view of the beach and ocean.

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.

"Jolly"- Houseboat Getaway
#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

Baywatch Upper-Waterfront & Roaming Ponies!
Calender open for super deals on weekly Summer rentals 2026. Beautiful space in and out! Vacation efficiency, situated right on the bay with views of Assateague across the way, Chincoteague ponies are on premises. Coastal charm at its finest, there are 2 queen bedrooms and livingroom/breakfast room, all with a view. No full kitchen. Microwave, toaster, small fridge, stocked Keurig coffee and tea station and shared outdoor cooking area, sink and bbq grill.

Secluded Waterfront 15mi to Beachβ’Kayaksβ’Fast WiFi
Casa Blue Heron is a 2,254 ftΒ² (209 mΒ²) custom home offering stunning water views, a firepit, and serene seclusion at our 3-bedroom waterfront sanctuary by Chincoteague Bay and near Assateague, Berlin, Ocean City, Snow Hill and much more. β "A private and tranquil setting where it is impossible not to relax and appreciate nature... Wish I had booked an extra day!" Add us to your wish list by clicking theβ€οΈin the upper-right corner.

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.

Bayfront Modern Retreat β’ Dock, Kayaks, Views
Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginiaβs Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.

Bayfront Cottage w/ Amazing Views
Whether youβre 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.

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 Assateague Island outdoor seating rentals
Holiday House Rentals with Outdoor Seating

The Neigh-Neigh - Location, Location, Location!

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Joy in the Morning @ Berlin Boho Bungalow

Chincoteague Island Creekside Cottage

Bayside community near OCMD great rates

Salisbury Hideaway

Rest A'Shored charming Chincoteague getaway

Mosaic Life Escapes -Bayfront Million Dollar Views
Apartment rentals with outdoor seating

Studio Condo Steps to the Beach

Private suite .5 mile from beach/no shared spaces

Newly Constructed 2nd-Story Studio Apartment

Little Slice of Cambridge. 2 bedroom, pet friendly

Endless Summer With Ocean View & Large Deck

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

West Ocean City: Private Studio, Close To Beach

Relax at the Shorehouse
Condo rentals with outdoor seating

Dewey Beach Condo 2BR+sofa bed. Walk to the beach!

ππͺππ¨π© πππ«π€π§ππ©π Lovely 2lvl Condo Steps 2Beach+Pool

Short walk to Beach & Boardwalk | 2BR/2BA Condo

Luxury at the Beach.

Mid-Town OC! Ocean Block... Steps to the Beach!

Oceanside Retreat | Steps to the Beach

Love Above the Waves-Best Ocean View & Heated Pool

Direct Oceanfront close to Northside Park!
Destinations to explore
- Rentals with an EV chargerΒ Assateague Island
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- Rentals with poolsΒ Assateague Island
- Rentals with a patioΒ Assateague Island
- Cottage rentalsΒ Assateague Island
- Townhouse rentalsΒ Assateague Island
- Family-friendly rentalsΒ Assateague Island
- Rentals with a fire pitΒ Assateague Island
- Rentals with beach accessΒ Assateague Island
- Rentals with a kayakΒ Assateague Island
- Rentals with a fireplaceΒ Assateague Island
- Beachfront rentalsΒ Assateague Island
- Fitness-friendly rentalsΒ Assateague Island
- Rentals with a washing machine and dryerΒ Assateague Island
- Pet-friendly rentalsΒ Assateague Island
- Rentals with outdoor seatingΒ United States




