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
Home in Woolford
4.93 out of 5 average rating, 143 reviews

Waterfront Getaway with Dock

MattRating, 5 stars1 month ago
I’ve enjoyed Trevor’s place each for the past few years. He’s a great host! Very responsive. Great communications. Always a pleasure!
Guest favorite
Home in Colonial Beach
4.94 out of 5 average rating, 17 reviews

Peaceful and Cozy Waterfront Home

AngelRating, 5 stars4 months ago
We enjoyed staying here The place was just as peaceful and relaxing as we hoped I would definitely recommend and stay here again if ever in town again
Guest favorite
Home in Shady Side
4.96 out of 5 average rating, 105 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

NicholasRating, 5 stars3 months ago
We had 6 people for a weekend retreat and this was a fantastic house and location for us. the host was super communacitive and easy/friendly to work with. We'll go back for sure next time we need a retreat space that is quiet, private and affordable.
Superhost
Home in Heathsville
4.92 out of 5 average rating, 124 reviews

The Hideaway at Mill Creek

RebeccaRating, 5 stars4 months ago
Everything about this home was perfect for our family of four that loves the Bay. Peaceful, amazing views, well stocked, comfortable, private pier with kayaks, a zillion movie and game choices, close to NNK towns. The hot tub was a bonus. By the end of the weekend we wanted to move in! And the next door pup Bella was the sweetest. Thank you, we will be back for sure!
Guest favorite
Home in Heathsville
4.94 out of 5 average rating, 36 reviews

Family & Pet Friendly Private Beach Retreat

JustinRating, 5 stars4 months ago
Responsive and communicative via AirBnb app. Open to small changes we had to make. Beautiful house and wonderful neighborhood. Everything as described and reasonable price. Truly provided the BnB part of AirBnb with linens, cleaning/cooking supplies, and bathroom supplies. Very scenic. The pictures don't do it justice when it comes to the proximity of the dock. It is right outside the window of the master bedroom.
Guest favorite
Home in Lancaster
4.94 out of 5 average rating, 16 reviews

The River House

WhitneyRating, 5 stars5 months ago
We had a relaxing weekend at the river. We had so much privacy and were super happy with the house
Superhost
Home in Scotland
4.91 out of 5 average rating, 126 reviews

Spacious Gorgeous Waterfront Home with Sunset View

DeborahRating, 5 stars3 months ago
Our family of 5 adults, 1 child and an infant had a lovely Thanksgiving visit to Karina's house in Scotland. The house was very spacious and comfortable for all. Our 5-yr old granddaughter was especially thrilled with 'her' room -- nicely decorated and quite suitable for her age. The other bedrooms had great mattresses (relatively new?) and the linens were all good quality. The kitchen had most of the items you'd need to make a big dinner and even bake. The location was very quiet and given the time of year, a peaceful retreat to simply enjoy the view of Tanner Creek. All in all it was a great spot for a family holiday gathering.
Superhost
Home in Dunnsville
4.74 out of 5 average rating, 141 reviews

Cozy & Content River Retreat Beach Hot Tub & Games

MichaelRating, 5 stars2 weeks ago
Incredibly peaceful and comfortable. looking forward to returning in warmer weather and for a longer stay. We were seeking a quiet place for renewal and relaxation and the little yellow cottage met all our needs. We stocked up on local seafood from nearby Warsaw to cook, woke up with the birds for breathtaking sunrises and soaked in the amazing hot tub with an incredible view. As a bird geek in training, I had an amazing assortment to watch and enjoyed the views from the dock and the deck each day. We experienced a heavy downpour for a great deal of our stay,but a trip to town and hunkering down with our books, puzzle and more hot tub were the perfect antidote. We might share the space with friends or family next time, as there was plenty of space. However, our trio of 2 humans and our puppy pal might just escape alone again! Thanks for sharing this letter slice of heaven on the "Rivah." We'll be back!

Cottage rentals with a kayak

Guest favorite
Cottage in Weems
4.99 out of 5 average rating, 105 reviews

The Crab Shack

KimberlyRating, 5 stars1 week ago
We loved The Crab Shack. It was a comfortable, cozy place right on the water with an outstanding view. The amenities were great! We felt like we were at home but in a really special location. We hope to return very soon!
Superhost
Cottage in Reedville
4.88 out of 5 average rating, 196 reviews

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

IsabellaRating, 5 stars1 week ago
Beautiful location! Such a great spot for relaxation. Melissa & Dave were very clear with their instructions, and very sweet couple! Great communication and accommodating. Hopefully we go back soon!
Superhost
Cottage in Warsaw
4.94 out of 5 average rating, 111 reviews

Modern 2 Bdrm Cottage in Historic River Community

StephanieRating, 5 stars3 weeks ago
This was my second stay at Renee’s cottage. It was as peaceful as I remembered. My husband and I had such a relaxing time, walking the dog and enjoying the wildlife, lounging in the overstuffed couches, and drinking our coffee on the screened in porch. One of our favorite places to stay.
Guest favorite
Cottage in Smith Island
4.97 out of 5 average rating, 219 reviews

Levering Creek Cottage with Private Docking

CaitlynRating, 5 stars2 weeks ago
We needed a place to chill and unwind and this was it! Not much to do this time of year but we didn't care. We loved every minute of our time on the island. Everyone was so friendly and we felt right at home. Beautiful sunsets and delicious catered meals. Thank you!!!
Guest favorite
Cottage in Annapolis
4.98 out of 5 average rating, 108 reviews

Weems Creek Cottage, Annapolis Waterfront

AmiraRating, 5 stars1 month ago
We had a lovely stay at Jim’s place. It is so quaint, quiet, and thoughtful. We loved the scenery, the bedside view of the sunset over the river was stunning. We slept so well, absolute peace and immediate comfort. It’s also in a really cute area, nice little local restaurants and cafes nearby, and we enjoyed walking/driving to downtown Annapolis. Only about 30 min walking & less than 10 min drive. Very easy to find, SO clean and very well designed, private and intimate, just really cute and charming spot. Jim was very friendly, responds immediately and provides all the information you could possibly need! We will definitely be returning in warming weather. Highly recommend!
Guest favorite
Cottage in Pasadena
4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars3 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 !
Guest favorite
Cottage in Hague
5 out of 5 average rating, 134 reviews

Potomac River cheerful cottage

JamesRating, 5 stars3 weeks ago
Want to get away? This retreat defines that. I am assuming for the winter months, only a handful of people are here. The dock and water were inviting but chilly for February. We brought all our food so we just chilled and took a long walk along the roads. This is the place to read a book, clear your minds, just unwind.
Guest favorite
Cottage in Montross
4.98 out of 5 average rating, 144 reviews

Newly Renovated 2BR Waterfront Cottage with Dock

TiffanyRating, 5 stars1 week ago
My husband and I visited for a little anniversary getaway. We brought our old pup and she loved laying on the deck, looking out at the water. We got lucky to have a beautiful weather weekend with temps in the 50s. We enjoyed the fire pit at night and opening up the living room doors for a nice indoor/outdoor feel. The home is located in the woods on a quiet street so I took some nice morning strolls with our pup. We went into town for coffee and takeout dinner and enjoyed Carolina Beach which is dog friendly in the winter and a short 25 min. drive. The downstairs bedroom stayed warm even with the barn style doors open, dropping the ac temp, and running the ceiling fan. The mattress was comfortable and the kitchen was well equipped for the meals we cooked in. We would definitely return again!

Cabin rentals with a kayak

Guest favorite
Cabin in Indian Head
4.97 out of 5 average rating, 32 reviews

*Private Waterfront Retreat w/3 Cabins Close to DC

CandiceRating, 5 stars1 month 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
Cabin in Lancaster
4.89 out of 5 average rating, 54 reviews

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

HollyRating, 5 stars1 month ago
We’ll be staying at this property quarterly this year and I’ll review it each time. For now, I’d just like to say…we feel at home. We are so grateful that we will be able to experience the seasons and magic of this beautiful land and home all year long in 2025.
Superhost
Cabin in Queenstown
4.89 out of 5 average rating, 19 reviews

Warm and Cozy Historic Cabin on the Water

CavanRating, 5 stars4 months ago
Great time, beautiful cabin and property!
Superhost
Cabin in Spotsylvania
4.74 out of 5 average rating, 126 reviews

Wilderness - Hot tub Rancher

DenaeRating, 5 stars1 week ago
I enjoyed my stay here with my partner. The location was great, close proximity to many stores and restaurants. The jacuzzi was the best part of the trip!
Guest favorite
Cabin in Lusby
4.9 out of 5 average rating, 252 reviews

Peaceful Waterfront Retreat on The Bay

HeatherRating, 5 stars1 week ago
Our stay at Camp Maier was everything we needed and MORE than we could have ever expected. We ended up staying a few extra days because THATS how much we wanted to hang on to the peace and serenity that we felt while there. We are definitely planning our next trip. Great hosts. Gorgeous cabin. Beautiful land/views. Definitely worth it.
Guest favorite
Cabin in Lusby
4.93 out of 5 average rating, 191 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

MollyRating, 5 stars1 week ago
We had a wonderful time at Lisa's place and were so impressed and charmed by the gorgeous spot, the tasteful decor, and the general peacefulness and coziness of the whole place. It was the perfect spot for a getaway with friends who just wanted a quiet and comfy place to catch up and relax together. Lisa was easy to get in touch with and incredibly helpful. We felt right at home and can't wait to return!
Guest favorite
Cabin in Mineral
4.96 out of 5 average rating, 112 reviews

Log Cabin Retreat on Lake Anna, private side!

DavidRating, 5 stars1 month ago
This was our family's second time here. It's hard to find a place that can accommodate a large group, including a couple seniors with special needs and two young kids. We were lucky to have snow, so had a great time playing in the very large backyard. The kitchen is well stocked, so did all our own cooking and we barely had to leave the house. We hope to be back again soon!
Superhost
Cabin in Mineral
4.87 out of 5 average rating, 31 reviews

Cabin on the Cove

MichelleRating, 5 stars2 months ago
We loved the outdoor spaces and the view of the lake from the living room! Plenty of hikes and wineries to go to in the area. We thoroughly enjoyed our stay and appreciated their flexibility as well!

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