Beachfront vacation rentals in Chesapeake Beach

Find and book unique beachfront homes on Airbnb

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Popular amenities for Chesapeake Beach beachfront rentals

Pet-friendly beachfront home rentals

Guest favorite
A serene waterfront scene captures a dock alongside a calm waterway, surrounded by lush greenery. An American flag waves at the dock, with a gravel road leading away from the water. The inviting atmosphere reflects the tranquility of the locale.
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 332 reviews

The Crab House - a Private, Waterfront Guest House

RosaRating, 5 stars2 weeks ago
This guesthouse is situated right on the water in a quiet, private neighborhood that is located close to restaurants, shopping, and recreation. The ambiance is relaxed, and we immediately felt at home. The decor is stylish in the gorgeous kitchen, and the heated bathroom facilities are spacious and accommodating. The bed was particularly comfortable, and the living room faces large windows and a continuous view of the waterfront. We enjoyed our stay in this location and highly recommend this property. We hope to visit again when we are in the area.
Top guest favorite
A spacious backyard is visible from the balcony, featuring a well-kept lawn and several trees providing shade. A play structure with a slide is situated on one side, while the house displays charming architectural details. Guests can enjoy a peaceful outdoor setting.
Guest suite in Dunnsville
5 out of 5 average rating, 266 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

DanielRating, 5 stars1 week ago
It ought to be a collection of Such's and So's. Such a nice place and so quiet. So well decorated with taste and quality materials. Such a relaxing spot so close to the water. So so so good cookies and muffins. And last but not least, so nice people. Very lively and cheerfull Tanya, very calm, quiet and peacefull John (still amazed, 40 years later and apparently, by his wife who may still have more energy than any soldier he faced throughout his carreer . Is there any use to add we enjoyed very much being there and highly recommend the Birds nest ? Daniel
Guest favorite
An open living space with large panoramic windows invites natural light. A compact kitchen is visible, equipped with appliances and a built-in shelf. A round dining table with white chairs is positioned adjacent to a cozy seating area, which features a soft gray sofa. A decorative rug enhances the warmth of the room.
Tiny home in Solomons
4.96 out of 5 average rating, 629 reviews

“Cabana by the Bay”-tiny home on a pier!

AbigailRating, 5 stars3 days ago
We really enjoyed our stay at the cabana! We loved how peaceful it felt, yet we were right there in the center of things when we wanted to get something to eat etc. Though small, the kitchen had everything we needed to cook a full breakfast. Truly a novel place to stay! I would recommend this place to anyone wanting a relaxing and unique place to stay on Solomons Island...
Top guest favorite
The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.
Apartment in Lexington Park
4.97 out of 5 average rating, 559 reviews

Historic St. Mary's City, MD

WendyRating, 5 stars4 days ago
The location was beautiful and the home was very cozy. Sitting on the screened porch, reading and enjoying the view of the yard and water was good for the soul. It was very quiet and we had all the amenities we needed.
Guest favorite
A serene lakeside scene features silhouetted trees framing a view of the water at sunset. A person sits in a plastic chair at a small table, overlooking the calm waters, creating a peaceful and reflective atmosphere.
Cottage in Pasadena
4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars5 months ago
The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !
Superhost
Cottage in Lottsburg
4.9 out of 5 average rating, 102 reviews

Charming Waterfront Home with Expansive Views

MichaelRating, 5 stars5 months ago
We loved the house; cozy, nicely decorated, with many pieces of original art that really added character. The kitchen is well stocked for those who like to cook. The location right on the water was wonderful, and Nancy provided kayaks, which we took advantage of. Our dog was beside himself with so much room to run. Nancy’s daughter and family live next door, and we spent quite a few hours enjoying conversation and local knowledge with them. We would go back again.
Superhost
The two-story house is set against a clear blue sky, featuring a spacious porch with ample seating. A stone fire pit is positioned in the yard, surrounded by grass, complemented by a pergola on one side.
Home in Dunnsville
4.75 out of 5 average rating, 143 reviews

Cozy & Content River Retreat Beach Hot Tub & Games

ChristineRating, 5 stars4 days ago
We had a great time at Nicholas and Dana's place! It was both fun and relaxing. We really enjoyed the little beach, the dock and the kayaks. We caught some catfish and one tiny crab in the crab trap (and threw everything back in). It was nice to have the firepit and hot tub to use too. And, the kids really liked being downstairs in their own space. The only issues were that the key pad wasn't working to get in to the front door which was frustrating after a long drive and the grill was very slow to heat up and probably needs to be replaced. Overall, this home was a really good choice for us and we would stay again when visiting family in the area.
Guest favorite
Apartment in Annapolis
4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

ThomasRating, 5 stars6 months ago
Wonderful host—I felt right at home. Had conversation prior to arrival and felt like I knew her very well before arriving. The view was spectacular I could have just sat on the patio and watched the woods and water all day. Was there for a school reunion so I had other activities that I had scheduled. This was by far, the best Air B&B experience I have had. Fantastic host, comfortable, and stunning scenery. I am going to try and revisit soon.

Beachfront home rentals with a pool

Top guest favorite
Home in Chestertown
5 out of 5 average rating, 22 reviews

Chestertown Watson Family Farm

TaraRating, 5 stars7 months ago
We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.
Top guest favorite
A wooden dock extends into calm waters, featuring two boats secured at the end. A colorful sail with bright red, yellow, and blue stripes stands upright, contrasting with the clear blue sky. Surrounding greenery creates a serene backdrop.
Home in Montross
4.98 out of 5 average rating, 42 reviews

Game-Themed Waterfront Fun! Dock-Boats-King Suite

NiyaRating, 5 stars4 weeks ago
I stayed here with my three kids for a little getaway, and we had the best time. The place was super clean and spacious, and the modern decor and finishes were clearly chosen with care—it just felt really good to be there. The game rooms were such a fun touch, each with its own theme, and the kids were obsessed! One of our favorite parts was the scavenger hunt—it was such a fun and unexpected surprise, and it gave us a memory we’ll definitely hold onto. The host was incredibly kind, polite, and respectful. Overall, it was just a great experience and a really special trip with my kids.
Top guest favorite
The backyard features a private pool surrounded by landscaped gardens and a variety of seating areas. Flowering plants add color to the foreground, while lounge chairs line the poolside. The house and trees are visible in the background, complementing the serene setting.
Home in Lusby
5 out of 5 average rating, 15 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

DeniseRating, 5 stars6 months ago
The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!
Guest favorite
A comfortable living area features a sectional sofa and two armchairs, complemented by a coffee table. Large windows allow natural light to fill the space, with a sliding door leading to a private balcony. A television is mounted on the wall opposite the seating.
Apartment in Colonial Beach
5 out of 5 average rating, 23 reviews

Sandy Feet Retreat - Beachfront

RosemarieRating, 5 stars2 weeks ago
Sandy Feet Retreat in Colonial Beach was a great place to take my daughter and the grandkids for a 3 day Spring Break holiday. The condo was beautifully furnished and very well located on the boardwalk. My family loved having access to the beach right outside the condo and spent many hours collecting shells and sea glass. Fishing from the pier was a thrill for my grandson. I enjoyed peaceful mornings on the balcony and evening time there listening to the waves each day. Thank you Brittany for everything you do to assure a lovely stay for your guests.
Superhost
A fenced swimming pool is visible under clear blue sky, with sunlight reflecting off the water's surface. Several white lounge chairs surround the pool, complemented by a shaded table and umbrella nearby. The area appears well-maintained and inviting for relaxation.
Condo in Betterton
4.92 out of 5 average rating, 36 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

CaitlinRating, 5 stars7 months ago
A great sunset view from the balcony, such a nice quiet river/bay beach, peaceful community to walk around. Would stay in again! Would note there’s 1 flight of stairs up as it’s a 2nd floor condo of sorts; and a big hill/stairs down to the beach. However, also a parking lot if needed to drive to the beach. Beach chairs were nice to have. There was no cooking oil but I think we left some :) I would only ask they replace the dining room chair with the hole in the seat. The pool was closed and that was not expected! Adam was very responsive when we messaged.
Superhost
A private, fenced-in pool area is shown, featuring a clear blue pool surrounded by a spacious patio. Lounge chairs are set around the pool, and a covered seating area is visible nearby, providing options for relaxation in a tranquil outdoor setting.
Cottage in Heathsville
4.83 out of 5 average rating, 75 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

AllyRating, 5 stars8 months ago
This was a wonderful getaway for my family and friends. We had two toddlers that loved the river beach and pool. There were plenty of toys to keep the kids and adults busy!
Top guest favorite
A spacious outdoor area features an inviting pool surrounded by lush greenery and vibrant landscaping. Colorful umbrellas provide shade over multiple seating areas, including lounge chairs and a dining table. The serene atmosphere is accentuated by the tranquil water and nearby trees.
Home in Kent Narrows
5 out of 5 average rating, 299 reviews

Chester Riverfront At Kent Narrows

MichaelRating, 5 stars1 week ago
Beautiful location on the water with all the amenities one could ask for. Thanks for having games and jigsaw puzzles (with all the pieces!). Gracious and responsive hosts who made sure we felt welcome and at home. We’ll be back!

Private beachfront home rentals

Guest favorite
An open living space is visible, featuring a comfortable sofa and a wooden coffee table. A dining area with black chairs is situated near a well-equipped kitchen, which includes stainless steel appliances. A large window allows natural light to fill the room.
Home in Middle River
4.95 out of 5 average rating, 20 reviews

The Shore House

JessicaRating, 5 stars1 week ago
House was spectacularly designed and smelled so good upon arrival. The ranch level style with everything on one floor was ideal for stay with a toddler (and 3 adults). We only stayed a weekend but wish it was longer. I would definitely stay here again. One thing to note that this area does not have service if you are not in the house. Once you are in the house you have WiFi and good to go. Lauren was super responsive and very nice.
Guest favorite
A charming yellow cottage features a welcoming porch with two comfortable chairs and a vibrant area rug. Lush green trees provide shade, while glimpses of the water are visible in the background under a clear blue sky.
Home in North Beach
4.92 out of 5 average rating, 64 reviews

A Little Piece of Paradise - Waterfront Home

MandyRating, 5 stars4 months ago
A great find, and just what we needed! It was perfect for my husband, myself and our teenage son. We took the upstairs bedroom and he had the downstairs bedroom. We loved the fire pit outside and having a front row seat to the bay. The house was quaint and just perfect for the three of us. We enjoyed walking around North Beach, and also enjoyed a couple of their great restaurants, even in the off season!
Top guest favorite
The living room features a cozy seating area with plush sofas and a coffee table placed on a textured rug. A decorative hanging chair and a wood stove add character, while large windows reveal expansive views of the waterfront, allowing natural light to fill the space.
Home in Colonial Beach
4.97 out of 5 average rating, 114 reviews

Sunrise Waterfront Potomac Beach Haus

CarmenRating, 5 stars3 weeks ago
Heather was an amazing host, and the home was absolutely beautiful. Waking up to the waterfront views and the peaceful early morning walks are only some of the reasons why I would stay again. If you are looking for a peaceful getaway, look no further.
Guest favorite
A spacious deck features a dining table surrounded by several chairs, providing a comfortable outdoor dining area. A grill is positioned nearby for cooking, with views of the surroundings, including trees and the shoreline of Chesapeake Bay in the distance.
Home in North East
4.86 out of 5 average rating, 72 reviews

The Beach House

KarenRating, 5 stars5 months ago
We had a small family group stay at the Beach House in North East for Thanksgiving, and it was perfect in every way for our group. Plenty of room, fantastic location and water views, easy beach access, very well-equipped kitchen, warm and cozy living room area, and great communication from Alexis. We hope to return again soon!
Guest favorite
The spacious waterfront deck features a clear view of the Chesapeake Bay, with soft sandy beach extending along the shoreline. Lush greenery lines the edge of the deck, providing a natural backdrop against the bright blue sky and calm water.
Home in Reedville
4.94 out of 5 average rating, 35 reviews

Summer Breeze waterfront new home-Private Beach

JamesRating, 5 stars1 week ago
This is a great place for a relaxing family getaway. The property is right on the water with a nice dock you can walk out on every morning. They even have chairs already out there so you can sit and drink your coffee, read, etc. The house itself was very clean with tons of supplies provided. There are grocery stores and restaurants not too far away. Would highly recommend.
Guest favorite
Home in Cobb Island
4.98 out of 5 average rating, 45 reviews

River Front 3 bedroom home with pier and beach.

JenniferRating, 5 stars5 months ago
Our family traveled from South Carolina for a funeral in LaPlata MD (a short drive away from this home). Jane's property was just what we needed to accommodate our family of 6. The house was clean, comfortable and well equip with everything that was needed. The ping pong table in the garage provided much needed entertainment when we had down time. The views were absolutely beautiful and we can not wait to come back. While there we enjoyed crabs at Captain John's crab house a couple of miles away. I would totally recommend this home to anyone that is traveling for business, leisure or just a peaceful, quiet getaway. Thanks Jane for your hospitality and sharing your beautiful home with us.
Guest favorite
A wooden deck area is highlighted with four Adirondack chairs arranged around a central fire table, where flames flicker gently. Beyond the deck, a well-maintained lawn leads to the bay, visible in the distance under a colorful sunset sky.
Home in Stevensville
4.96 out of 5 average rating, 89 reviews

25-50% Off~Private Beach~Hot Tub~Fire Table~

KeelanRating, 5 stars3 weeks ago
Beautiful house in a picturesque location. My daughters enjoyed wading into the Chesapeake Bay from the (small) private beach on the property and drawing pictures in the sand. We also enjoyed watching a heron that was hanging out for a while on the neighbor's pier (the binoculars provided that Nancy and Tom provided were a nice addition).
Guest favorite
Home in Lusby
4.92 out of 5 average rating, 12 reviews

Chesapeake Bay Waterfront View

KathrynRating, 5 stars6 months ago
My husband and I stayed a weekend to celebrate our anniversary. Beautiful view , amazing sunrise. Great restaurants near by. The home was very comfortable.

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