Chesapeake Beach beach vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Chesapeake Beach vacation rentals

Stay near Chesapeake Beach's top sights

Chesapeake Beach Water Park16 locals recommend
Hook & Vine - Kitchen and Bar18 locals recommend
Neptune's Seafood Pub9 locals recommend
Sweet Sues Bake Shop & Coffee14 locals recommend
Chesapeake's Bounty3 locals recommend
North Beach Farmers' Market3 locals recommend

Chesapeake Beach vacation rentals

Superhost
Home in Annapolis
5 out of 5 average rating, 14 reviews

Book for CW Water views, parking, porch, dogs ok

MichelleRating, 5 stars3 months ago
The place was perfect and we loved watching the sunrise over the bay every morning. Nice quiet neighborhood and great fenced in backyard for the dogs. The house was as described and looks like the photos. The host was very responsive and helpful! Would definitely recommend this home to anyone looking to come to the Annapolis area.
Guest favorite
A spacious screened porch features several white wicker chairs surrounding a coffee table. Ceiling fans rotate overhead while large windows provide expansive views of the water. The area includes a dining table and some colorful beach towels neatly organized on the wall.
Home in Montross
4.93 out of 5 average rating, 202 reviews

The Glebe

Irma VRating, 5 stars2 weeks ago
We loved the open space concept in the house. It has beautiful views and a fire pit. Beds were clean and comfortable. Very well supplied kitchen. We will come back. Thanks,
Guest favorite
A sandy beach stretches along the water's edge, bordered by a calm lake. Rocky jetties extend into the water, and trees provide shade in the background. A few people are scattered along the shore, contributing to a serene atmosphere.
Home in Rock Hall
4.95 out of 5 average rating, 37 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 week ago
It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"
Guest favorite
A wooden dock extends into the water, framed by a sandy beach and green foliage. An American flag gently flutters, while the sun’s rays create a shimmering effect on the calm surface of the water. The sky displays wispy clouds, adding depth to the serene scene.
Cottage in Colonial Beach
4.87 out of 5 average rating, 89 reviews

Bungalow Private Beach & Dock Colonial Beach Water

EricaRating, 5 stars2 weeks ago
We had a great time at Nate’s Airbnb. The beach access was awesome. Waking up to the bird song was one of my favorites
Top guest favorite
An outdoor hot tub features a sleek design with built-in jets, illuminated by soft purple lighting. The surrounding area is draped with white curtains, creating a secluded atmosphere. Seasonal use is indicated, adding a touch of relaxation to the outdoor space.
Place to stay in Annapolis
4.94 out of 5 average rating, 121 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

PaulRating, 5 stars1 week ago
We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.
Superhost
Cottage in Saint Michaels
4.77 out of 5 average rating, 26 reviews

Cottage #1 Lighthouse First Cottage down driveway

AngelicRating, 5 stars31 months ago
This was the 2nd time we stayed at Harris Cove. Beautiful property just a few minutes from St. Michaels. The cottages are cozy and have everything you need. We love it there and will be returning. Alex and Jaimie are awesome hosts and greeted us upon arrival. Wonderful long weekend away that is relaxing and alot of to do as well!
Guest favorite
A large tree provides shade over a grassy area, with a view of a calm waterfront. A wooden pier extends into the water, flanked by lush greenery. The scene is serene, evoking a sense of relaxation and natural beauty.
Home in Deale
4.98 out of 5 average rating, 106 reviews

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

CarolRating, 5 stars2 weeks ago
Our family had a great time - the property was spacious and clean, location was beautiful, and we loved playing outdoors in the open space and getting out on the water. Hosts were very responsive and everything we might need/want was provided!
Top guest favorite
A serene exterior view of the home is framed by tall trees and a well-maintained lawn. The structure features a spacious porch and multiple entrances, while a paved driveway leads up to the front. A colorful sky enhances the tranquil setting.
Home in Spotsylvania Courthouse
5 out of 5 average rating, 20 reviews

The Upper Level

AudraRating, 5 stars5 months ago
I would highly recommend this home to anyone looking to stay in that area!! Very comfortable space and the host was very accessible and accommodating!! 5 stars for sure!!!

Other great vacation rentals in Chesapeake Beach

Top guest favorite
A serene backyard scene is captured at sunset, featuring a concrete patio with four chairs arranged around a small table. A shed is visible in the distance, alongside lush green grass and mature trees. The sky displays a gradient of colors as daylight fades.
Home in Fruitland
4.97 out of 5 average rating, 130 reviews

Amazingly convenient yet secluded.

MaryRating, 5 stars1 week ago
Keith was always prompt in responding to questions and was very friendly. The house was easy to get to and had plenty of things to do around the area. We were very happy with our stay and will definitely stay again.
Guest favorite
A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.
Home in Edgewater
4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

NancyRating, 5 stars3 weeks ago
Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.
Guest favorite
A sunlit corner of a room features large windows offering views of the waterfront and lush greenery. A spacious bed with a textured white coverlet is in the foreground, complemented by a yellow accent chair and a small round table set up beside a work desk.
Home in Deale
4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

CourtneyRating, 5 stars1 month ago
This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.
Superhost
A spacious living area features a large sectional sofa positioned around a coffee table, with a geometric area rug beneath. A flat-screen TV is mounted on the wall, and natural light streams in through large windows, enhancing the open layout that flows to the dining area.
Home in Pasadena
4.86 out of 5 average rating, 58 reviews

Beautiful Home Near Beach and Patapsco River

EvaRating, 5 stars1 month ago
This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.
Guest favorite
A row of charming urban townhouses features a blend of red brick and stone exteriors. A large tree stands in front, providing natural shade. The street is lined with parked vehicles, indicating a vibrant neighborhood. The sky is bright with scattered clouds.
Apartment in Canton
4.97 out of 5 average rating, 32 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

RachelRating, 5 stars2 weeks ago
Jenny’s place was exactly what we needed for our long weekend trip. I loved that it was spacious, clean and had excellent natural light. We spent lots of time walking through the park across the street and appreciated how quiet the street/block was at night. 10/10 would recommend!
Top guest favorite
The exterior of the house is showcased with a charming wrap-around porch, flanked by neatly trimmed landscaping. A three-story structure features shingle siding and multiple large windows that allow ample natural light. The front entrance is accessed via a set of stone steps.
Home in Arlington
4.97 out of 5 average rating, 100 reviews

Entire family size house steps to ANC & metro walk

Mary EllenRating, 5 stars1 month ago
Tyler's place was perfect for our stay with our extended family. It's spacious and comfortable, with plenty of room to relax indoors and out. It has a very nice large porch and deck, great for some solitude or for kids to play. The beds were comfy and the linens ample, there are gorgeous large bathrooms and luxurious showers, the kitchen was well-stocked and included an amazing high-end stove, and the living spaces are nicely decorated and furnished with art and tons of books. One bedroom had lots of toys and kids' books, a very nice touch. Tyler was helpful, accommodating, and responsive. The location is very convenient to Arlington National Cemetery and within walking distance to a Metro stop. Everything about this rental was fantastic--we highly recommend it if you need a lovely space for a large group. Thanks, Tyler!
Superhost
The house is positioned among leafy trees, featuring numerous large windows that brighten the interior. A spacious deck is visible, along with a hot tub. A stone fire pit surrounded by wooden chairs is located in the foreground, inviting outdoor gatherings.
Home in Montross
4.88 out of 5 average rating, 232 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

SarahRating, 5 stars2 weeks ago
This cabin was everything we wanted and more! It’s in the perfect location, just a short drive to so many activities but also tucked away offering privacy. The house was so cozy it put us at ease as soon as we walked in. The owner was proactive and very quick to respond, including sending a great packing and local activity list a couple days in advance of our trip which came in very handy. Activities: This rental comes with guest passes to the private Shark Tooth Beach where our kids had so much fun finding real shark and manta ray teeth in the sand! Westmorland State Park and George Washington’s Birthplace both had great hiking and beaches for the kids. We visited Garners Produce twice where the kids fed animals and pedaled toy tractor’s while we picked up farm fresh milk and eggs. We spent our afternoons kayaking on the quiet lake soaking up the sunshine. We will definitely book another vacation at this cabin. You will not be disappointed with your stay at this little gem!
Superhost
A wooden deck is visible, surrounded by trees adorned with autumn foliage. The serene lake reflects the vibrant colors of the leaves, creating a peaceful outdoor space perfect for relaxation.
Cabin in Lusby
4.84 out of 5 average rating, 171 reviews

2-bedroom lake-house with a magnificent view

MohamedRating, 5 stars3 weeks ago
Beautiful house and beautiful view. Outdoor jacuzzi with the view is not to be missed! Gorgeous and clean home. The private site made it an amazing getaway from busy life. Thank you, we will be back soon!!!

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