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

Rod 'N' Reel Restaurant51 locals recommend
Chesapeake Beach Water Park44 locals recommend
Hook & Vine - Kitchen and Bar31 locals recommend
Neptune's Seafood Pub29 locals recommend
Sweet Sues Bake Shop & Coffee27 locals recommend
Chesapeake's Bounty27 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 stars2 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.
Superhost
A spacious living area features elegant armchairs in soft hues, accompanied by a round wooden coffee table. A traditional area rug adds texture, while large windows dressed in blue curtains allow natural light to fill the room. A fireplace and decorative furnishings enhance the atmosphere.
Home in Wye Mills
4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

LisaRating, 5 stars11 months ago
Kevin is a great host to us year after year! we love staying at his place!
Superhost
A sandy beach stretches along a calm shoreline, edged by gentle waves. The clear blue sky mirrors the tranquil water, creating a serene atmosphere. Tall grasses provide natural borders along the beach, with distant trees visible on the right side, offering a sense of peaceful seclusion.
Cottage in Saxis
4.86 out of 5 average rating, 218 reviews

ISLAND SUNSETS Near Chincoteague Island

AndrewRating, 5 stars1 day ago
Great, comfortable place to stay for a visit to Saxis and the eastern shore. Well-kept with all necessary amenities.
Guest favorite
A spacious rooftop deck is presented, featuring comfortable seating arranged around a fire pit. A patterned area rug adds texture to the wooden surface. Clear views of the sky and surrounding greenery create an inviting atmosphere for relaxation.
Condo in Colonial Beach
4.96 out of 5 average rating, 47 reviews

Rooftop bay and river views

AlisaRating, 5 stars1 week ago
House was great with space for everyone whether we gathered for a meal or game wanted to spread out. Super easy walk to the beach and boardwalk. GREAT coffee shop and a few gems of restaurants and shops-we were definitely there in off season and the town was not fully opened - lots of opportunity in the town and lots of places getting opened for the season! Would be a great place for a quick summer getaway
Guest favorite
An outdoor deck is surrounded by lush trees, providing a secluded atmosphere. Comfortable seating is arranged around a central table, with decorative cushions adding a touch of color. A grill stands at the edge of the deck, offering outdoor cooking options. Water views are visible through the trees.
Home in Heathsville
4.9 out of 5 average rating, 81 reviews

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit!

ManuelRating, 5 stars3 months ago
We took a small vacation with my sister’s family and we loved the location. Our kids enjoyed the small play area in the basement with the arcade machine and foosball table. We cooked every night and they had all useful appliances. We used the Ninja air fryer and Keurig machine every day. Since we went in January after a snowstorm the road was a little hazardous to use and the lake was completely frozen, so we spent most times indoors. We did enjoy going to the dock and looking at the frozen lake. This will be a great place to visit during the summer, they had Kayaks to use and a nice dock to jump from and fish. We would definitely come back.
Superhost
Home in Saint Leonard
5 out of 5 average rating, 3 reviews

Waterfront Home, Spectacular View & Private Beach!

AmberRating, 5 stars1 month ago
I had a wonderful stay at this beautiful house over looking the bay! The views all around the property were absolutely stunning, creating such a peaceful and relaxing atmosphere. I was on a work trip with several coworkers, and the house was incredibly comfortable and spacious —it truly felt like home. The space was clean, safe, and well-maintained, making it the perfect retreat after long workdays. The kitchen was fully stocked with everything needed to prepare a large family meal, which was a huge plus. Most importantly, our host was amazing—she was incredibly kind, attentive, and thoughtful, anticipating our needs before we even had to ask. I would absolutely stay here again and highly recommend this property to anyone looking for a serene and welcoming getaway. Thank you, for such a great experience!
Top guest favorite
A charming home is presented with a yellow front door and blue windows. A white picket fence encloses the front yard, while a small porch is defined by two steps leading to the entrance. An American flag is displayed outside.
Cabin in North Beach
4.93 out of 5 average rating, 59 reviews

1943 Beach House Walk to Town & Beach & Boardwalk.

LatanyaRating, 5 stars1 month ago
I was in town for work, and this place was perfect. It was walkable to several restaurants and to the calming water. Christopher was a wonderful host and very responsive. I'd definitely stay again if in town.
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 stars1 week 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!

Other great vacation rentals in Chesapeake Beach

Guest favorite
An aerial view captures a tranquil property nestled by a serene cove. The two-story home features a light exterior with a dark roof. A wooden dock extends into the water, adorned with seating and kayaks, surrounded by lush greenery and open fields.
Home in White Stone
4.92 out of 5 average rating, 24 reviews

Relax Waterfront Hot Tub, Game Room, Frisbee Golf

EmilyRating, 5 stars1 month ago
We loved our weekend at Camden Cove! Beautiful scenery, relaxing atmosphere, fantastic amenities. Highly recommend enjoying a long weekend (or longer!) here.
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 stars4 weeks 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.
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 stars3 weeks 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
Home in Germantown
4.8 out of 5 average rating, 54 reviews

Sophia’s victorian

Simrnjit KaurRating, 5 stars1 week ago
Perfect place for our stay in Germantown. Very cozy and the kitchen was fully stocked with cookware. Plenty of rooms for everyone to have their own space and also the family room was big enough for everyone to hang out together.
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, 231 reviews

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

SarahRating, 5 stars1 week 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 stars1 week 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!!!
Guest favorite
Home in Colonial Beach
4.94 out of 5 average rating, 68 reviews

The Heaven at Colonial Beach

MelissaRating, 5 stars2 months ago
I’ve stayed at a lot of Airbnb’s and this was easily one of the best. Everything was exactly as described, and maybe even better than described. It had tons of amenities and a well stocked kitchen perfect for our large family. Spotless and beautiful. I highly recommend this home and would gladly stay there again.
Guest favorite
A spacious parking area is visible in front of a single-story house, surrounded by large trees. The building features a welcoming porch and two garage doors. An expansive blue sky complements the serene outdoor setting.
Home in Leonardtown
4.87 out of 5 average rating, 15 reviews

Garden Getaway

LindsayRating, 5 stars1 month ago
We had the pleasure of staying here during the winter while we looked for a place to live. It was perfect! Quiet and peaceful yet super close to all restaurants and stores. We had some snowfall and the views were stunning! Once it warmed up we even got to see some wild life in the woods behind us. Lovely huge porch! Lots of space in garden escape. Can bring the entire family and more!!! Nice big driveway for easy turned around. Patrick was beyond responsive for all my questions.Whether is was just informing be as something as simple as an Internet outage in the area or we had one situation with an unsure smell. Patrick acted immediately on the problem and it was resolved within 2 hours from start to finish. Cannot recommend this place enough!

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