Vacation rentals with a kayak in Southern Maryland

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Popular amenities for Southern Maryland kayak rentals

House rentals with a kayak

Top guest favorite
A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.
Home in Woolford
4.93 out of 5 average rating, 151 reviews

Waterfront Getaway with Dock

SarahRating, 5 stars2 weeks ago
We loved the experience from booking to check-out. The setting exceeded our expectations. Peaceful and beautiful landscape. Easy to launch kayaks. Chickens were an added bonus. Appreciated the close proximity of Blackwater. Would love to return.
Top guest favorite
A rack holds three colorful kayaks—green, yellow, and purple—resting on a natural landscape of brown leaves. A wooden dock extends into the calm water, lined by trees in the distance, showcasing the tranquil surroundings ideal for kayaking and relaxation.
Home in Heathsville
5 out of 5 average rating, 46 reviews

Northern Neck Creek Retreat w/ king suite, firepit

JulietteRating, 5 stars3 weeks ago
Creek Retreat is a perfect place to kick back and relax. Surrounded by nature, a private oasis. The space is well appointed, clean and comfortable. Tastefully decorated. Added amenities and attention to details elevate the experience. Enjoy kayaking and sitting by the fire. Georgia is a great hostess and is proactive and responsive. If you're looking for a getaway, book it here!
Superhost
A gentle sunset casts warm hues over a serene waterfront scene. The coastline features a lighthouse near a small, two-story building, with a pier extending into the water. Lush greenery surrounds the area, creating a peaceful atmosphere.
Home in Piney Point
4.86 out of 5 average rating, 51 reviews

2 Bedroom Cozy Beach Cottage

WillieRating, 5 stars1 month ago
Michelle is a great host. The place is clean and has many conveniences. I highly recommend!
Top guest favorite
A spacious room features large windows that provide views of the calm Patuxent River. A wooden table with several stools sits in the center, and a telescope is positioned beside the window, inviting observation of the serene landscape.
Home in Prince Frederick
5 out of 5 average rating, 16 reviews

Downs By The River

JeffRating, 5 stars1 week ago
We had a very enjoyable stay at this perfect River House. The place was warm and comforting, with some of the most amazing views you can find. We arrived shortly after check in time, and easily let ourselves in with the lock box code & key. Everything inside looked just like the pictures, and we weren't disappointed! If you're looking for some beautiful river views, right on the water, with your own private water access and dock, this is the place for you. We were in town for a wedding a few houses down, and this place couldn't have been any better for us. We were able to walk to & from, which was a huge bonus for after the reception...Cheers :) We enjoyed eating out a couple times in town, and really liked Brick Wood Fired Bistro & Traders Seafood Steak & Ale. We would highly recommend this property for anyone looking for a peaceful river stay, and will surely return someday in the future! Thanks for your hospitality!
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 stars2 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!
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 stars2 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.
Top guest favorite
The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.
Home in Lusby
4.99 out of 5 average rating, 212 reviews

Cove Point Cottage with Chesapeake Bay views

LynnRating, 5 stars6 days ago
Very nice house in a great walkable neighborhood. Host were very helpful and responsive.
Top guest favorite
A circular fire pit made of blocks is surrounded by six colorful adirondack chairs in bright hues of red, orange, yellow, green, blue, and turquoise. The setting overlooks a calm body of water, framed by trees and a dock in the distance.
Home in Reedville
4.95 out of 5 average rating, 175 reviews

Panoramic Waterfront: Fire pit, Game Room, Kayaks!

LoriRating, 5 stars2 weeks ago
stayed with family, very comfortable, loved being on the water. took out a kayak, and much fun with corn hole. Enjoyed watching baby osprey from backyard!

Cottage rentals with a kayak

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 stars1 month 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, 113 reviews

Cottage with a view!

GraceRating, 5 stars3 weeks ago
Beautiful place to stay. Quite peaceful area with friendly neighbors. Home was cozy and welcoming. Kitchen had everything you could need. Amenities were amazing. Had a spectacular time would definitely come back to stay again.
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, 210 reviews

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

LorenRating, 5 stars2 weeks ago
We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.
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
A waterfront cottage is set against a backdrop of lush greenery, with a stone wall bordering the water. The well-maintained lawn extends towards the river, and the cottage features a covered patio, inviting outdoor seating, and a surrounding cluster of trees.
Cottage in Cobb Island
4.97 out of 5 average rating, 62 reviews

Where Eagles Soar *Stunning Waterfront Views*

NancyRating, 5 stars1 week ago
My friends and I immediately felt relaxed and cared for in this delightful home. We loved that it was right on the water and that we could enjoy seeing the Potomac River from so many rooms. The beds were very comfortable. Sue is a thoughtful and very pleasant host. We enjoyed our stay very much.
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 stars1 day 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!
Top guest favorite
Cottage in Annapolis
4.98 out of 5 average rating, 115 reviews

Weems Creek Cottage, Annapolis Waterfront

AmyRating, 5 stars6 days ago
Cottage is very cute and the perfect size for a couple. Beautiful view and has all the necessary amenities. Jim was very responsive and communicative!
Top guest favorite
A serene view of a wooden dock extending into calm waters, reflecting hues of blue, orange, and pink from the sunset. Soft clouds drift in the sky, complementing the tranquil ambiance of the waterfront scene.
Cottage in Leonardtown
4.96 out of 5 average rating, 94 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

ElizabethRating, 5 stars1 week ago
Perfect location. Spent all our time on the dock and porch when it was too sunny.

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!
Superhost
A sunlit deck extends alongside the cottage, featuring smooth wooden planks. Two chairs and a small table are positioned invitingly near the edge, with tall trees providing shade and a view of the bay beyond.
Cabin in Reedville
4.73 out of 5 average rating, 22 reviews

"Elderberries" Chesapeake Bayfront Cottage

JoelRating, 5 stars1 month ago
We enjoyed our stay here. Very quiet area, nice comfortable space. The gravel road leading in (maybe a half-mile long) and driveway gave us a good area for morning and evening dog walks. We did not end up doing any fishing but the pond looked like a great place for kayak fishing. Not specific to the house but in the area: Rita's Cafe in Weems was great (food truck on a small road)--Chef Craige usually has a special and some regular menu items. Leadbellys (at Fairport Marina) had good oysters and hush puppies and was convenient for our first night. River Market in White Stone has good food to be ordered at the rear counter and prepared items in the coolers. Out of the Oven Bakery (White Stone) had great bread Miss Mary's seafood, also in White Stone had great fresh fish and prepared items. The three places in White Stone are very close to each other so convenient when running out.
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 stars6 days 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.
Superhost
The exterior of the historic cabin is showcased, featuring a dark blue facade with a white entrance door. Flowerpots flank the entrance, and landscaped gardens present vibrant floral hues. A glimpse of the dock along the river is visible in the background, framed by mature trees.
Cabin in Queenstown
4.9 out of 5 average rating, 21 reviews

Cozy Historic Cabin on the Water

KrystalRating, 5 stars3 weeks ago
Staying at Shawna and Keith's cabin was a wonderful experience. Peaceful and serene, it was relaxing just to wake up in this private oasis. Shawna and Keith were very friendly and easy to get in touch with if we had any questions. They even provided items for some of the activities we decided to try while staying there. The cabin was clean, quaint, quiet, well-equipped; and looked exactly as described. We would definitely return for another weekend getaway! Thanks again!
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 stars2 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 stars2 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, 40 reviews

Luxury cabin - Pond - 16 acres

DanielleRating, 5 stars2 weeks ago
We had a great stay at Blake's place! the fire pit and grill were easy to use. We loved how peaceful the home and surrounding areas were. Thank you for a great stay!

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