Chesapeake Beach beach vacation rentals

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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

Vacation rentals in Chesapeake Beach

Guest favorite
Home in Montross
4.93 out of 5 average rating, 200 reviews

The Glebe

LynnRating, 5 stars1 month ago
Excellent stay at RivahLife! The views were spectacular and the home was exactly as described. Easy to find with lots of stuff for the kids and adults. Looking forward to returning during the warmer months as the fishing, boating, and swimming would be more desirable. Thanks for the high chair and portable crib. Those things really help when traveling with kids.
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, 31 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

RachelRating, 5 stars2 days 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!
Guest favorite
A person is seen kayaking on calm waters, with a lighthouse in the background. The kayak is gray with orange and blue accents. The scene captures a peaceful moment on the water, emphasizing the tranquility of the Chesapeake Bay.
Apartment in Annapolis
4.94 out of 5 average rating, 17 reviews

Crow’s Nest Cottage - Down Under: Chesapeake Bay

RickRating, 5 stars1 month ago
I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.
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
4.94 out of 5 average rating, 36 reviews

Rockfish Keeper

Kore MichaelRating, 5 stars5 months ago
The house was exactly as described and it was so easy to communicate with them as they responded to texts within minutes
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
A pair of glass French doors provides a view of the outdoor seating area and pool. Bright red chairs are positioned around a fire pit on a stone patio, framed by a lush green lawn leading to the water.
Home in Tilghman Island
4.97 out of 5 average rating, 30 reviews

Relax by the Water - Summer Dates Available!

RonnieRating, 5 stars3 months ago
Absolutely beautiful home! highly recommend!
Guest favorite
A wooden deck offers a view of the grassy yard leading to the waterfront. Boats are visible on the water, with trees in the background providing a natural setting. The scene is illuminated by natural sunlight, enhancing the tranquil outdoor atmosphere.
Home in Essex
4.86 out of 5 average rating, 51 reviews

Waterfront getaway Essex, MD

YannerysRating, 5 stars2 weeks ago
A great place to spend time with the family with incredible views
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.

Other great vacation rentals in Chesapeake Beach

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, 142 reviews

House in Edgewater Maryland

NancyRating, 5 stars1 week 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 custom-built residence is presented with a blend of stone and wood accents. Large windows illuminate the inviting front porch, surrounded by manicured landscaping and a lush green lawn. The two-story structure is set against a backdrop of trees, offering a sense of privacy.
Home in Annandale
4.94 out of 5 average rating, 18 reviews

Family Ready Dogs OK Ping Pong Backyard EV Charger

AngelaRating, 5 stars1 month ago
Absolutely gorgeous home. ALL the amenities! Master bedroom is HUGE. Master shower is superb!! All bedrooms are nice sized and all have their own bathroom. Basement is really nice too. Can’t say enough good about this home. Would definitely rent again!!
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 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 stars3 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.
Guest favorite
Home in Cambridge
4.98 out of 5 average rating, 126 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

RobertRating, 5 stars4 days ago
Excellent host! Great communicator and went out of her to make sure we didn't have any issues. Lovely place for a family get away!
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
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 stars5 days 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!
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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