Holiday rentals with a kayak in Southern Maryland

Find and book unique kayak rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for kayak rentals in Southern Maryland

House rentals with a kayak

Superhost
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 favourite
Home in TYLERTON
4.96 out of 5 average rating, 134 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

SusanRating, 5 stars3 weeks ago
Wonderful accommodations for a relaxing visit to a beautiful island!
Superhost
Home in Scotland
4.9 out of 5 average rating, 134 reviews

Spacious Gorgeous Waterfront Home with Sunset View

KathrynRating, 5 stars6 days 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!
Guest favourite
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 favourite
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!
Top guest favourite
Home in Colonial Beach
4.97 out of 5 average rating, 72 reviews

River Refresh - Waterfront with Spa on Placid Bay

YuRating, 5 stars3 days ago
Nicola’s place is beyond the photos and descriptions! We have good time there and had the luck to experience the beauty of both rainy and sunny days there. The house is beautifully renovated and pristine clean. Every single spot is well equipped with a lot of surprising details. The screened porch is the perfect to enjoy the view no matter what weather , and free of bug/mosquitoes inside! River view Hot tub is very relaxing. We are also able to enjoy Kayaking, crabbing (several biggest blue crabs I’ve ever caught) along the river and never get bored among the peaceful environments surrounding!
Top guest favourite
Home in Heathsville
5 out of 5 average rating, 38 reviews

Waterfront Cabin! FishCrab~BigPorch~Paddle~Karaoke

Sasha LernerRating, 5 stars1 day 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
Top guest favourite
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 favourite
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 favourite
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
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
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 favourite
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 favourite
Cottage in Smith Island
4.97 out of 5 average rating, 229 reviews

Levering Creek Cottage with Private Dock

ErikRating, 5 stars4 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!
Top guest favourite
Cottage in Tall Timbers
5 out of 5 average rating, 47 reviews

Charming Waterfront Cottage with Sunset Views

LeslieRating, 5 stars3 weeks ago
We had an amazing holiday weekend at Dave and Jenny’s cottage! They were always so quick to respond with any requests we had! The cottage as perfect and just like the pictures. They literally had thought of everything! The sunsets were absolutely stunning and it was truly the most relaxing time we’d had in a while! It was just what we needed !
Top guest favourite
Cottage in Leonardtown
4.96 out of 5 average rating, 95 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

WendyRating, 5 stars2 days ago
I think this is my 5th time staying there. Always thinking of my return visit before even leaving!

Cabin rentals with a kayak

Guest favourite
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 favourite
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
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
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.
Superhost
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 favourite
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.
Top guest favourite
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 favourite
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!

Destinations to explore