Beachfront vacation rentals in Southern Maryland

Find and book unique beachfront homes on Airbnb

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Popular amenities for Southern Maryland beachfront rentals

Pet-friendly beachfront home rentals

Guest favorite
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
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
Tiny home in Solomons
4.96 out of 5 average rating, 629 reviews

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

AbigailRating, 5 stars2 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...
Superhost
Apartment in Cambridge
4.91 out of 5 average rating, 124 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

LesleyRating, 5 stars4 months ago
We had a winter visit and despite it being freezing outside the house was nice and toasty and we appreciated the fast hot water for showering. No fenced yard for our dog but it's a nice area to walk around. Central location, close to restaurants. Would stay again.
Top guest favorite
Apartment in Lexington Park
4.97 out of 5 average rating, 559 reviews

Historic St. Mary's City, MD

WendyRating, 5 stars3 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
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.
Guest favorite
Home in Onancock
5 out of 5 average rating, 17 reviews

Leave your paw prints by the bay

RobertRating, 5 stars5 months ago
Excellent home. Was attached to another dwelling but felt very private as no one was next door during our stay. Host was very accommodating, neighbors extremely friendly. Lots of dogs being walked in the surrounding area. Roads very safe to go for an extended walk. Winds coming off the water surprisingly strong at times; was impressed at how secure the house seemed during stormy winds. Best part of the stay was being right on the water of the river/bay.

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
Home in Montross
4.98 out of 5 average rating, 41 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
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
Apartment in Colonial Beach
5 out of 5 average rating, 23 reviews

Sandy Feet Retreat - Beachfront

RosemarieRating, 5 stars1 week 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
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
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
Home in Colonial Beach
4.83 out of 5 average rating, 18 reviews

Doug's Paradise

MatthewRating, 5 stars4 months ago
Stayed here to see a few friends who live in the Ebb Tide area. The house was clean, spacious and well equipped. We were only two people but with the sun room it was clear to see there are a few options for people to spread out and not feel on top of each other. This is a nice peaceful area about 15 minutes away from downtown colonial beach and a great location for a getaway. I would stay here away without hesitation.
Guest favorite
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!
Superhost
Cabin in Lusby
4.84 out of 5 average rating, 171 reviews

2-bedroom lake-house with a magnificent view

MohamedRating, 5 stars2 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!!!
Guest favorite
Home in Colonial Beach
4.98 out of 5 average rating, 60 reviews

Waterfront Paradise with own Beach, Kayak, & Grill

SonjaRating, 5 stars5 months ago
We loved this snug, little spot on the water. Watching the sunrise over the water made for enjoyable mornings. It had a full kitchen that made cooking our meals very easy. Two seating areas in the living area gave us room to spread out. Fast wifi....I even stayed online while I was down by the water. I wasn't a huge fan of the overly curious swans, but I did find some really nice pieces of sea glass down by the water. The heat in this house was great.
Guest favorite
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
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.
Top guest favorite
Home in Cambridge
4.95 out of 5 average rating, 80 reviews

Osprey's Retreat - Waterfront with private beach!

lindaRating, 5 stars1 week ago
We had such a great getaway at Salman’s house on the river! The views were spectacular. The neighborhood was very quiet and peaceful and we slept great on the comfy beds. The fresh ground coffee in the morning was such a nice touch. We stayed during the week off-season, and Salman was kind enough to allow an early check in and late check out to round out the perfect stay, and was always quick to reply (although we didn’t need much.) It was only warm enough to enjoy the yard and beach one day, would love to come back in the warmer weather. But the inside views from every room were so nice we didn’t miss much. Thank you Salman for a great trip!

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