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Waterfront vacation rentals in Assateague Island

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Assateague Island

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

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Townhouse in Ocean City

4.85 out of 5 average rating, 189 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 in Onancock

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

Cottage in Onancock

4.96 out of 5 average rating, 227 reviews

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<<

Guest favourite

Home in Millsboro

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 in Chincoteague Island

4.97 out of 5 average rating, 207 reviews

Jay’s Retreat: EV Charger-Fire Pit-Kayaks-Bikes

Welcome to Jay's Retreat, your perfect escape just minutes from Assateague National Seashore and the iconic Chincoteague Ponies! This fully equipped 1,000 sq. ft. home features 3 cozy bedrooms, a fire pit for starry nights, kayaks, bikes, and a private dock for your water adventures. Enjoy swimming, fishing, hiking, and bird watching right at nature’s doorstep. With linens and towels included, plus an EV charger for your convenience, you’ll have everything you need for a memorable getaway.

Guest favourite

Apartment in Selbyville

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 in Chincoteague

4.9 out of 5 average rating, 110 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 in Ocean Pines

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!

Home in Onancock

4.9 out of 5 average rating, 59 reviews

Escape To A “True” Chesapeake Waterfront Property!

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 "Bayview House", an updated 1950's cape cod featuring lots of original features with many modern upgrades. It sits on our 44-acre property along with our "Sunset House" - also available on Airbnb.

Houseboat in Snow Hill

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

Condo in Dewey Beach

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

Cottage in Easton

5 out of 5 average rating, 100 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

Vacation rentals for every style

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Quaint homes, peaceful surroundings

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Hotels

Stylish accommodations and amenities

Popular amenities for Assateague Island waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Ocean City

5 out of 5 average rating, 4 reviews

The Pelican of Bahia Vista 3B/2b

Guest favourite

Apartment in Ocean City

4.96 out of 5 average rating, 56 reviews

Canal Front Condo 2 Blocks 2 Beach & Park Sleeps 4

Guest favourite

Apartment in Ocean City

5 out of 5 average rating, 24 reviews

Bayside Bungalow - Waterfront

Apartment in Ocean City

4.8 out of 5 average rating, 10 reviews

Bayfront Ponte Vista ~ 211

Guest favourite

Apartment in Ocean City

4.96 out of 5 average rating, 28 reviews

Driftwood Condo, 1BRTropical Bayside w/sunsetview

Guest favourite

Apartment in Chincoteague

4.85 out of 5 average rating, 165 reviews

Sunset Haven Downtown

Apartment in Ocean City

4.71 out of 5 average rating, 28 reviews

3br Waterfront Assateague Island Best View

Guest favourite

Apartment in Ocean City

4.93 out of 5 average rating, 15 reviews

Crystal's Catch of the Bay!

Waterfront house rentals

Guest favourite

Home in Woolford

4.93 out of 5 average rating, 139 reviews

Waterfront Getaway with Dock

Guest favourite

Home in Ocean Pines

4.99 out of 5 average rating, 118 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

Guest favourite

Home in Woolford

5 out of 5 average rating, 115 reviews

Starboard on McKeil Point, w/heated pool & hot tub

Guest favourite

Home in Woolford

5 out of 5 average rating, 218 reviews

Newly Renovated Modern 3 bed 2 bath Water Front

Guest favourite

Home in Cambridge

4.89 out of 5 average rating, 18 reviews

Waterfront & Hot Tub! 4 BR/4 BA - Central Location

Guest favourite

Home in Bethany Beach

4.87 out of 5 average rating, 47 reviews

Waterfront, SUPs, Yaks, & Bikes! Walk 2 the Beach

Guest favourite

Home in Lewes

4.98 out of 5 average rating, 177 reviews

Beautiful Waterfront Home-Private, Clean, Relaxing

Guest favourite

Home in Cambridge

4.95 out of 5 average rating, 74 reviews

Osprey's Retreat - Waterfront with private beach!

Waterfront condo rentals

Guest favourite

Condo in Ocean City

4.95 out of 5 average rating, 39 reviews

Entire Downtown Bayfront Condo

Condo in Ocean City

4.88 out of 5 average rating, 51 reviews

Waterfront Condo w/ Balcony, Right on the Canal

Condo in Ocean City

4.85 out of 5 average rating, 40 reviews

Penthouse condo. Bayside with elevator. Wow Views!

Guest favourite

Condo in Ocean City

4.85 out of 5 average rating, 101 reviews

1st Floor 3 BR Condo close to Beach with Pool!

Guest favourite

Condo in Ocean City

4.87 out of 5 average rating, 71 reviews

UNIQUE Bay Front Sanctuary Condo

Guest favourite

Condo in Ocean City

4.98 out of 5 average rating, 212 reviews

Direct Oceanfront close to Northside Park!

Guest favourite

Condo in Ocean City

5 out of 5 average rating, 60 reviews

Blue Haven I Bay I Boatslip I BoardwalkI Inlet

Guest favourite

Condo in Ocean City

4.88 out of 5 average rating, 129 reviews

Water Front Condo w/Pool Short Walk to Beach

Destinations to explore