Vacation rentals with a kayak in Southern Maryland

Find and book unique kayak rentals on Airbnb

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Popular amenities for Southern Maryland kayak rentals

House rentals with a kayak

Guest favorite
A serene view showcases a dock extending into calm waters at sunset. Silhouetted Adirondack chairs are positioned facing the horizon, where the sun dips below the water, casting a warm glow across the sky and reflecting on the tranquil surface.
Home in Lottsburg
4.96 out of 5 average rating, 48 reviews

Waterfront Escape!

RoxanneRating, 5 starstoday
We had such a nice visit! Ryan was very responsive to questions and requests. The house is very cute and perfect for a family with kids. Lots of toys and games and outdoor equipment - and a fun tree swing! The little sandy area was just right for our three kids (ages 1, 4 and 7). We ate all our meals outside on the deck overlooking the water. The neighbors were very friendly. Everything was great!
Top guest favorite
A peaceful waterfront retreat is nestled among trees, showcasing a two-story blue house with a spacious deck. The property features a rock shoreline leading to a calm beach area, offering a serene setting by the water. The surrounding landscape is lush and inviting.
Home in Lusby
5 out of 5 average rating, 17 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

AlanRating, 5 stars4 days ago
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!
Top guest favorite
The exterior of a restored home built in 1860 is shown, featuring light-colored siding and a gabled roof. The porch is framed by green grass and various potted plants, contributing to a welcoming atmosphere. A flag can be seen displayed near the entrance.
Home in TYLERTON
4.96 out of 5 average rating, 134 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

SusanRating, 5 stars4 weeks ago
Wonderful accommodations for a relaxing visit to a beautiful island!
Superhost
Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.
Home in Scotland
4.9 out of 5 average rating, 134 reviews

Spacious Gorgeous Waterfront Home with Sunset View

KathrynRating, 5 stars1 week ago
My family of 10 had a great stay here! There was plenty of space to spread out and the location is perfect and serene. We were able to fish out on the dock and caught a few spot! One of the friendly neighbors even stopped by to offer some raspberries from their bush and extra firewood. We did run into an issue after check in with one of the bathrooms, but Karina was quick to respond and sent someone out to handle it as quickly as possible. Thank you for the wonderful stay!
Superhost
Aerial view of a long wooden dock extending over calm waters, leading to a covered boat area. Reeds surround the water's edge, and a charming house is visible in the background under a colorful sky, adding to the serene riverfront setting.
Home in Dunnsville
4.75 out of 5 average rating, 144 reviews

Cozy & Content River Retreat Beach Hot Tub & Games

ChristineRating, 5 stars1 month ago
We had a great time at Nicholas and Dana's place! It was both fun and relaxing. We really enjoyed the little beach, the dock and the kayaks. We caught some catfish and one tiny crab in the crab trap (and threw everything back in). It was nice to have the firepit and hot tub to use too. And, the kids really liked being downstairs in their own space. The only issues were that the key pad wasn't working to get in to the front door which was frustrating after a long drive and the grill was very slow to heat up and probably needs to be replaced. Overall, this home was a really good choice for us and we would stay again when visiting family in the area.
Guest favorite
A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.
Home in Montross
4.96 out of 5 average rating, 76 reviews

Waterfront home, private dock

ShufanRating, 5 stars3 weeks ago
We had a wonderful vacation here. Although it rained during our stay, we found the treehouse to be a great place just for listening the rain drops and having some inner peace.
Guest favorite
A private dock extends over calm waters, providing access to the waterfront oasis. Surrounding trees display vibrant autumn colors, reflecting in the water, while a covered area at the end of the dock offers a spot for relaxation. The serene landscape invites tranquility.
Home in Montross
4.95 out of 5 average rating, 66 reviews

Luxury Modern Waterfront Retreat

MalikRating, 5 stars3 weeks ago
Kelly and Thomas were amazing host. Very responsive and accommodating The home was very clean and the location was great.. 10/10. Definitely would book again!
Top guest favorite
A wooden dock extends into a calm body of water, surrounded by greenery. The sky above features a mix of soft clouds and blue hues, reflecting off the tranquil surface. The dock is supported by multiple wooden posts, enhancing the serene waterfront view.
Home in Heathsville
5 out of 5 average rating, 38 reviews

Waterfront Cabin! FishCrab~BigPorch~Paddle~Karaoke

Sasha LernerRating, 5 stars2 days ago
5 stars! Well deserved! From the beginning to the end! Jian is the great host. Very helpful, friendly and super responsive! The place is awesome, exactly like the photos. We enjoyed watching movies on the screened in porch, bird watching, fishing, kayaking, relaxing on the dock, playing games inside, karaoke too. The place is very comfortable and has everything even more than you need. I really appreciate how much thought went into lighting, decor and convenience with QR codes and labels. Some days it was raining and we took our 7yo to Compass Entertainment center, which is 30 min away. I recommend checking it out. Last before the departure was a storm and we lost power and WiFi, the reception is bad without the WiFi but the host notified us promptly and kept us informed about what’s going. Customer service was excellent! We enjoyed our time at LaMemoriia

Cottage rentals with a kayak

Top guest favorite
The exterior of The Crab Shack is showcased, featuring a metal roof and a spacious deck. A bike rests against the railing, with picnic tables positioned nearby. The structure is surrounded by greenery, reflecting in the calm water of Carter's Creek.
Cottage in Weems
4.99 out of 5 average rating, 115 reviews

The Crab Shack

TarynRating, 5 stars1 week ago
This was our 1st visit to The Crab Shack. All I can say is Wow, just Wow! This was the cleanest, nicest and cutest Airbnb that we have ever stayed at over the years! It was amazing! My husband and I traveled from Sarver, PA with our 2 Golden Retrievers to celebrate our 10 year Wedding Anniversary! We all had the best time ever! We spent most of the time here at the Shack just cooking on the grill and listening to music and the girls did a lot of swimming fetching for balls! Thank you Carlisle and Mary for making our 10 year Anniversary simply perfect! ❤️☀️😎🥂🍾🦀 We can’t wait to come back! ☺️
Guest favorite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale
4.96 out of 5 average rating, 160 reviews

Chesapeake Bay Cottage

MargaretRating, 5 stars2 months ago
Lovely stay on the water! Mini beach is an added bonus. Great restaurants nearby!
Guest favorite
An inviting deck features a turquoise picnic table and comfortable seating with floral cushions, offering views of Cod Creek. Large windows span the cottage facade, allowing natural light to fill the interior. Surrounding trees provide a serene backdrop.
Cottage in Heathsville
4.87 out of 5 average rating, 114 reviews

Cottage with a view!

HollyRating, 5 stars1 week ago
We came to relax and it was successful. A cute little cottage by the river.
Superhost
A covered deck offers seating with wicker chairs and colorful cushions overlooking the calm waters of the Chesapeake Bay. The decking is made of warm-colored wood, and a gentle view of the shoreline can be seen in the distance, enhancing the serene atmosphere.
Cottage in Reedville
4.88 out of 5 average rating, 211 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

TheresaRating, 5 stars3 days ago
If you are looking for a beautiful and peaceful location to unwind, this is a great place! The home is very comfortable and has everything you could need. But the highlight was the amazing views of the bay from practically every window in the house. We would definitely recommend staying here!
Superhost
A remodeled cottage is set amidst a green lawn, featuring a spacious screened front porch and surrounded by trees. The building showcases a classic design with a dark exterior and a contrasting light roof, under a clear blue sky.
Cottage in Warsaw
4.93 out of 5 average rating, 120 reviews

Modern 2 Bdrm Cottage in Historic River Community

C. CaliRating, 5 stars3 weeks ago
Loved staying at this quiet retreat! Mornings listening to birds, afternoons in the sunny backyard, stars and stars! Really loved this place and will be back again.
Top guest favorite
The exterior of the cottage is shown, featuring a welcoming entryway with stairs and a blue door. Two blue adirondack chairs are positioned on the well-maintained lawn, with a glimpse of the waterfront visible through large windows. Surrounding greenery enhances the outdoor setting.
Cottage in Smith Island
4.97 out of 5 average rating, 229 reviews

Levering Creek Cottage with Private Dock

ErikRating, 5 stars5 days ago
Janet has a unique property considering the destination is on an island... it has it's own dock which affords guests the ultimate in flexibility. It was the main reason we elected to overnight there. My son and I only had one night for the fishing trip in our own boat over father's day weekend so it was not a deal-breaker we had to book 2 nights. The simplicity of motoring up after a day on the water with all of our gear and the convenience for being up early to catch the right tide was a perfect fit. Wish we had 2 nights to stay and have better luck with the weather... and the fish, but we will be back. Thanks Janet!
Guest favorite
A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.
Cottage in Edgewater
4.99 out of 5 average rating, 157 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

SusanRating, 5 stars3 weeks ago
I had an amazing stay for my wedding weekend. The view of the water was unbeatable and the brand new outdoor furniture was great! Heather was very responsive and it was overall a great place to stay!
Guest favorite
An aerial view captures a secluded Victorian cottage surrounded by a private lake and lush landscaping. The cottage features a green roof and is accessed by a footbridge. Open land and water can be seen in the background, creating a serene retreat.
Cottage in Hacksneck
4.94 out of 5 average rating, 122 reviews

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

KariRating, 5 stars4 days ago
Pretty Bird Cottage was a magical place to spend a quiet few days unplugged with family. Would recommend to anyone looking for a peaceful getaway. It’s pretty secluded, so we planned groceries on the way there rather than venturing out for most meals. Also, cell service is spotty so be sure to keep the door code instructions somewhere you can access them offline. It was a wonderful vacation!

Cabin rentals with a kayak

Guest favorite
A sleek Scandinavian micro home made of spruce is set against a backdrop of colorful autumn foliage. Large windows provide ample natural light, while a patio area features comfortable seating and dining options. The surrounding lawn is well-maintained, creating an inviting outdoor space.
Cabin in Indian Head
4.97 out of 5 average rating, 32 reviews

*Private Waterfront Retreat w/3 Cabins Close to DC

CandiceRating, 5 stars4 months ago
This place could not be more perfect for our trip to DC. It was the perfect distance to the metro. Our group of 8 had so much space of our own, yet plenty of room to be together in the common spaces and not be on top of each other! We went in the coldest month of the year, so unfortunately we didn’t get to experience the best of what the outdoor areas had to offer but the views were breathtaking regardless. Melanie’s place was extremely clean and everything was provided and then some! Everyone in our group would like to go back in warmer months to spend more time outside. Before we got there, Melanie explained that there was an issue with one of the sinks in the cabins and said she would credit us accordingly. I thought that was great! It did not hinder or create a problem whatsoever! I hope we get to make it back sometime!
Guest favorite
Cabin in Saint Michaels
4.99 out of 5 average rating, 112 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

KateRating, 5 stars2 weeks ago
WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.
Superhost
A log cabin with a rustic exterior is surrounded by lush greenery. The wraparound porch features a wooden railing and an American flag hangs proudly. A detached garage is visible in the background, and the property is set against a peaceful lake.
Cabin in Lancaster
4.9 out of 5 average rating, 58 reviews

Riverside R&R: Cabin, Dock, Kayak & Game Arcade

LisaRating, 5 stars1 week ago
We are two families that met up for a relaxing getaway after celebrating a high school graduation. This was the perfect place. The downstairs had lots of games and a big screen for them to hook their switch up to. We watched movies upstairs. And use the well-equipped kitchen each night to make a big dinner. The kids took the kayaks and canoe out one afternoon as well. Although I would say they definitely wouldn’t swim there. Compass entertainment complex is very close and they enjoyed their time there. We also went to a movie there one night. It is a beautiful home in a peaceful setting. Especially down on the dock at night. It was very quiet. We would definitely recommend this home.
Guest favorite
An aerial view showcases the property surrounded by tall trees, with a clear path leading to a waterfront area. The serene water reflects the sunlight, while the landscape features a mix of greenery and open space, highlighting the tranquility of the setting.
Cabin in Ridge
4.95 out of 5 average rating, 65 reviews

Pizza Friday

LoisRating, 5 stars3 weeks ago
Pizza Friday was an amazing find! We spent a family reunion on the porch making pizza's in the oven. We obtained crusts from an Italian restaurant in California on our way and it proved to the perfect choice for us. We also enjoyed the dock and even caught a few crabs to show the kids. In addition we sat around the fire pit in the evenings. The beds were comfortable and everything was clean inside although we spent most of our time outside on the porch.
Superhost
The image displays a wooden cabin with a hot tub on a spacious deck overlooking the calm waters of Cool Springs Lake. Surrounding trees provide a natural backdrop, enhancing the serene lakeside setting.
Cabin in Spotsylvania
4.75 out of 5 average rating, 159 reviews

Wilderness Resort- Hot tub Rancher

RossRating, 5 stars3 weeks ago
Amazing peaceful place
Top guest favorite
A serene lakeside view features a wooden dock extending into the calm water, flanked by greenery. Two kayaks are displayed on a rack, while a fire pit with seating is positioned nearby. A safety notice is visible, ensuring guest awareness.
Cabin in Lusby
4.98 out of 5 average rating, 90 reviews

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

LaurenRating, 5 stars3 weeks ago
We stayed at Julie’s home with a group of friends and our families and had a wonderful time. The lakefront setting was incredibly relaxing—we found ourselves rarely leaving the property because it had everything we needed. From soaking in the hot tub to enjoying the game room, there was something for everyone. The kids loved having space to run around in the basement, while the adults enjoyed peaceful mornings and evenings on the screened-in porch. Julie was very responsive and answered all of our questions quickly, which made the entire experience seamless. We would absolutely stay here again!
Top guest favorite
Cabin in Manquin
5 out of 5 average rating, 41 reviews

Luxury cabin - Pond - 16 acres

EmilyRating, 5 starstoday
This property was gorgeous! The house was clean, spacious, and comfortable, and we loved relaxing on the porch and the dock. Blake was very responsive and communicated check-in/check out instructions well. The location feels serene and remote, but it is just a short drive away from a grocery store, multiple places to eat, Kings Dominion, and a local theater. The kitchen is a bit bare-bones, so be sure to bring everything you need if you plan to cook. We would love to come back in the future!
Guest favorite
A serene waterfront view showcases calm waters reflecting the sky, bordered by trees. A wooden dock extends into the water, framed by lush greenery. The soft colors of sunset illuminate the scene, creating a tranquil atmosphere in this natural setting.
Cabin in Reedville
4.97 out of 5 average rating, 261 reviews

Dinna Fash-3 BR Waterfront Log Cabin

AndrewRating, 5 stars2 weeks ago
So relaxing! So cozy! Such a cool spot and neighborhood! All the little details didn’t go unnoticed!

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