Beachfront holiday rentals in Southern Maryland

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in Southern Maryland

Pet-friendly beachfront home rentals

Top guest favourite
Guest suite in Dunnsville
5 out of 5 average rating, 265 reviews

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

DanielRating, 5 stars2 days 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 favourite
Tiny home in Solomons
4.96 out of 5 average rating, 626 reviews

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

KatelynRating, 5 stars4 days ago
So peaceful! Mad we haven't found this place sooner
Superhost
Flat 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 favourite
Flat in Lexington Park
4.97 out of 5 average rating, 558 reviews

Historic St. Mary's City, MD

MatthewRating, 5 stars2 weeks ago
We had a very enjoyable place in such a unique space -- right on the water with an amazing pier. The hosts made excellent recommendations.
Top guest favourite
Home in Shady Side
5 out of 5 average rating, 163 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

KathyRating, 5 stars6 days ago
We had a fantastic stay at Evan’s place. The cottage is beautiful and we really appreciated the lovely touches (fresh eggs, butter, dog biscuits). The property is beautiful and we enjoyed the calm waters of the bay and watching the ospreys. Highly recommend for a lovely and relaxing get away!
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.
Top guest favourite
Home in Fishing Creek
4.96 out of 5 average rating, 27 reviews

Waterfront Sunrise Cottage on Hoopers Island, Md

ShengfengRating, 5 stars4 months ago
We had 3 great night stay. Toby and Kim are super kind, they provided a lot of info. before we arrived, and responded very fast. The cattage is very nice, not very modern, but lovely, and the environment is quite and cozy.
Guest favourite
Home in Port Republic
4.88 out of 5 average rating, 25 reviews

Magical Bayfrnt Home, Pier, Beach, Fossils, trails

SkyeRating, 5 stars3 months ago
An extraordinary place to rest & recharge. The views, the comfort of the home, and the gorgeous walking trails, through woods & beach are a perfect combination. Everything we needed & then some.

Beachfront home rentals with a pool

Top guest favourite
Home in Montross
4.98 out of 5 average rating, 41 reviews

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

NiyaRating, 5 stars3 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 favourite
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 favourite
Flat 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.
Guest favourite
Home in Fishing Creek
4.95 out of 5 average rating, 37 reviews

Bay Front Villa on Chesapeake

RskRating, 5 stars3 months ago
Overall it was great stay. Laura was ready to accommodate my group of 22 ppl and had ample space. It was quiet and private place and we enjoyed the weather a lot. Clean place
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 favourite
Home in Kent Narrows
5 out of 5 average rating, 297 reviews

Chester Riverfront At Kent Narrows

MichaelRating, 5 stars3 days 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 favourite
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 favourite
Home in North Beach
4.92 out of 5 average rating, 64 reviews

A Little Piece of Paradise - Waterfront Home

MandyRating, 5 stars3 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 favourite
Home in Colonial Beach
4.97 out of 5 average rating, 113 reviews

Sunrise Waterfront Potomac Beach Haus

CarmenRating, 5 stars2 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.
Superhost
Home in Colonial Beach
4.67 out of 5 average rating, 12 reviews

Welcome to our beach house.

DavidRating, 5 stars6 months ago
This place is wonderful! Awesome views and wildlife! So quiet you can hear the birds wings flap in the air. Host was very responsive and we Definitely will return.
Superhost
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 favourite
Home in Colonial Beach
4.98 out of 5 average rating, 60 reviews

Waterfront Paradise with own Beach, Kayak, & Grill

SonjaRating, 5 stars4 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 favourite
Home in Reedville
4.94 out of 5 average rating, 35 reviews

Summer Breeze waterfront new home-Private Beach

JamesRating, 5 stars1 day 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.
Top guest favourite
Home in Lottsburg
5 out of 5 average rating, 17 reviews

Hideaway Home - 1st Pet FREE,Private Beach,Hot Tub

JamesRating, 5 stars5 days ago
We had a very relaxing retreat at this beautiful home in this peaceful location. Great outdoor space with hot tub and fire pit overlooking the beach, kayaks, dock, and a nice big deck. Excellent birdwatching and found some fun local restaurants and things to do in the area too. Hope to return!

Destinations to explore