Waterfront holiday rentals in Assateague Island

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Top-rated waterfront rentals in Assateague Island

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Guest favourite

Home

4.96 out of 5 average rating, 101 reviews

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

Superhost

Townhouse

4.85 out of 5 average rating, 191 reviews

DownByTheBay 115- Waterfront/4BR/Sleep 15/Pool

On The Bay, Beautifully furnished 4BR/3.5BR located in the heart of Midtown Ocean city, MD. * 1 block to beach- 5 min walk * Bonfire Buffet, Dough Roller, Ice cream Parlor - 2 min walk * Mini golf - 2 min walk * Bowling - 5 min walk * OC Boardwalk -7 minute by car * Seacrets - 5 minute by car * Convention Center - 5 minute by car * bus stop -1min walk * Market64- 2min drive *This property DOES NOT provide linens/towels* **Please FIND us at Down by the Bay OCMD For current Promotion**

Guest favourite

Home

4.8 out of 5 average rating, 139 reviews

Charming Waterfront Cottage on Cedar Creek

Come unwind in this comfy cottage right on the water. Situated on a 2 acre wooded lot, this colonial home offers peaceful seclusion and unbelievable water views from every room. This 1930’s cottage has modern updates and plenty of room, with two large bedrooms downstairs and a delightful bedroom suite upstairs. Restaurants and shopping await in the historic town of Onancock, only a 5-minute drive or an even quicker boat ride away. Private dock for swimming and fishing, two kayaks for guest use.

Guest favourite

Home

5 out of 5 average rating, 9 reviews

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

Guest favourite

Home

5 out of 5 average rating, 5 reviews

Waterfront Luxury Vacation Home!

5 oversized bedrooms, large living space for family time with a direct view of Little Assawoman Bay. It is just a few minute drive to Fenwick Island, closed to grocery stores, restaurants and gas stations. It is the most desirable community in Delaware Beaches. Waking up in the primary bedroom with a view of sun rising from water will make your day start with smiles! Not in the primary? You can enjoy the same water view on the main level balcony. Also enjoy our spectacular community amenities

Guest favourite

Home

4.98 out of 5 average rating, 40 reviews

Waterfront, Bring your own boat! Huge canal home.

Look no further for your vacation rental at the beach, this house has it all! Extraordinary waterfront coastal home with amazing views of the Assawoman Bay and the Ocean City skyline. With 2 expansive living areas with open floor plans, there is plenty of space for multiple parties to unwind. Relax on the deck or in the yard and enjoy the canal breezes. Cook in the updated kitchen and enjoy panoramic water views! Enjoy the beach in Fenwick Island, DE/Ocean City, MD just over 2 miles away.

Guest favourite

Flat

4.91 out of 5 average rating, 204 reviews

Dirickson Creek Waterfront Apartment

Spoil yourself in this 5 Star One bedroom ,great view of Dirckson’s Creek . Sunsets from a private waterfront deck or your private little beach & creek bar. 2nd floor over the garage with outside steps and private entrance. This apartment is very private u won’t be disappointed. No pets No Children three kayaks and stand up paddle boards to explore the Creek. We also have two beach chairs and umbrella for your use. Fresh ground coffee provided. Your own gas grill. Great for couples

Guest favourite

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!

Guest favourite

Home

4.91 out of 5 average rating, 166 reviews

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

Superhost

Houseboat

4.77 out of 5 average rating, 124 reviews

"Serendipity"- Houseboat Getaway

Serendipity is docked at an active marina with watermen and pleasure cruisers, nestled off the Chincoteague Bay. Sleeps up to 4 adults craving coastal tranquility. From the boat, the Chincoteague Bay is in view and ready to be explored. Enjoy a full spectrum of awe-inspiring coastal wetlands, historic downtown areas, and beaches all within a few minutes' drive. Truly, the perfect setting for a much deserved recharge. 35 Minutes from Ocean City, Assateague Is, and Chincoteague Is.

Guest favourite

Apartment

4.84 out of 5 average rating, 192 reviews

On the Bay, Private Beach-Boat Slip

Enjoy your own piece of paradise! Walk out the door 10 steps to the water! Modern condo located on the bay with great views, a patio, a grill, a private beach, boat slip, and 2 blocks to the ocean. Perfect for couples and small families! This is a well-appointed 500 sqft open concept condo with 1 bedroom, office & 1 bath. We take great pride in our condo and keep everything updated. New living room furniture Spring 2021. Completely renovated in mid 2020.

Guest favourite

Home

4.98 out of 5 average rating, 122 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!