Waterfront vacation rentals in Chincoteague Bay

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chincoteague Bay

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

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Guest favorite

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 153 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Guest favorite

Home in Onancock

4.8 out of 5 average rating, 141 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.

Top guest favorite

Cottage in Onancock

4.95 out of 5 average rating, 235 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<<

Top guest favorite

Home in Gloucester Courthouse

4.97 out of 5 average rating, 309 reviews

"Bee-Z Haven" Waterfront Cottage on the Ware River

Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Guest favorite

Home in Deale

4.98 out of 5 average rating, 106 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

3 Bedroom, 2 Bath Waterfront Paradise. This rustic rambler on Broadwater Creek in Churchton, MD, is a family vacation dream. A compound spanning 8 acres with over 700 feet of Waterfront will allow you to fish, crab, paddleboard, kayak, and enjoy the waterfront dream. Located near the small quaint waterman town of Deale, MD, you may never want to leave this relaxing area with direct access to the Chesapeake Bay. Brand new 140ft pier with views straight out to the bay, crabbing, and fishing!

Guest favorite

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Top guest favorite

Apartment in Lexington Park

5 out of 5 average rating, 374 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Guest favorite

Condo in Dewey Beach

4.84 out of 5 average rating, 193 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 favorite

Home in Cambridge

4.98 out of 5 average rating, 126 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!

Superhost

Home in Cambridge

4.9 out of 5 average rating, 107 reviews

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!

Guest favorite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 331 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

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What guests are saying

Waterfront 5 Bedroom Home Close to Annapolis

5 out of 5 average rating, 32 reviews4 months ago

Our family gathering was just wonderful due in large part to the home exceeding our expectations. First, host Laura could not have been any more helpful and responsive. Add to that was a beautifully laid out home for a small gathering that was well stocked and filled with of amenities. I would encourage anyone who is looking for a beautiful place within close proximity to Annapolis and Baltimore to seriously consider this home. Thanks again!

Vacation home in Severna Park

What guests are saying

Lighthouse View - Waterfront, Lighthouse Views

5 out of 5 average rating, 17 reviews6 months ago

Television is how I go to sleep. I specifically told you I need that before I arrived. The tv in the bedroom should have detailed instructions with the remotes. I tried everything but only got it to come on for 10 minutes once and not at bedtime. I did figure out the one downstairs tv worked but doing the same upstairs didn't work. I tried all inputs and stayed on the one you had on the tv. This caused me not to be able to sleep. This was a problem for me. More lightening on the back steps would be good. In the hallway from the car is great. Carpet upstairs isn't good. The small window by the deck door is torn in in 2 places.

Townhouse in Chincoteague

What guests are saying

Serene getaway with great waterfront views!

5 out of 5 average rating, 34 reviews7 months ago

We recently had a wonderful stay at Travis's place, and we couldn't have felt more at home. The house is not only beautiful but also comfortable, making it the perfect retreat. It’s one of the best-stocked homes I’ve encountered on Airbnb, which made our stay even more enjoyable. Travis was a wonderful host, always responsive and ready to assist with any questions. I truly hope to return in the future. Thank you, Travis, for hosting us in your lovely home!

Home in Cambridge

What guests are saying

Waterfront on the James 4,100 SF near Williamsburg

5 out of 5 average rating, 69 reviews6 days ago

Really nice quiet place on the James River. Kitchen and living room/breakfast area served our family really well. The house is close to the Jamestown ferry which allowed us easy access to the historical sights of Jamestown, Williamsburg and Yorktown and some great restaurants in Williamsburg. A great place.

Home in Surry

What guests are saying

Oyster House Waterfront Retreat - 90 min to DC

4.88 out of 5 average rating, 34 reviews4 months ago

The only thing that could have made our stay better would have been a longer visit in the summertime. Elizabeth has very lovingly and thoughtfully restored this beautiful home. We came in for a weekend full of celebrations and get togethers for a Navy retirement. The Oyster House was very comfortable for our family to sit down to unwind before going to bed to get back at it again in the morning. There were 5 people in our party, and we had no issues with everyone being able to shower. The linens were plush and plentiful. If we have the opportunity to return to Leonardtown The Oyster House will be our place.

Home in Leonardtown

What guests are saying

Waterfront Solomons Apartment

4.7 out of 5 average rating, 30 reviews5 days ago

We had a great stay. This place is tucked away and private, but also close to the action- plenty of restaurants, bars, and recreation. Park your car and walk everywhere. Don’t be afraid to bring your dog. This is a great spot for having adventures with your pup or for leaving them in the apartment for a bit. Space was clean and comfortable. Hosts were proactive and accommodating. We hope to come back.

Apartment in Solomons

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