Vacation rentals with a kayak in Southern Maryland

Find and book unique kayak rentals on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Popular amenities for Southern Maryland kayak rentals

House rentals with a kayak

Guest favorite

Home in Woolford

4.93 out of 5 average rating, 139 reviews

Waterfront Getaway with Dock

JustinRating, 5 stars2 months ago
Great place for a family va-k...
Guest favorite

Home in Colonial Beach

4.94 out of 5 average rating, 17 reviews

Peaceful and Cozy Waterfront Home

AngelRating, 5 stars2 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
Superhost

Home in Heathsville

4.92 out of 5 average rating, 123 reviews

The Hideaway at Mill Creek

RebeccaRating, 5 stars1 month 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, 35 reviews

Family & Pet Friendly Private Beach Retreat

JustinRating, 5 stars2 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 stars3 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 Montross

4.91 out of 5 average rating, 160 reviews

Tranquil River Home

AmberRating, 5 stars1 month ago
We absolutely loved our stay! The house was beautifil and well maintained and just as described. The view was MAGNIFICENT from the back deck! We saw bald eagels flying over the Potomac and shrimp boats going up and down the shore. This home is one of the best pet friendly airbnbs I have stayed in. They have dog bowls and a doggie door! If you want a nice getaway with no big city vibes, this is truly it! We loved getting away and just hanging around the house. We did explore Westmoreleand State Park, Stratford Hall and George Washington's birthplace. We hope to be back sooner, rather later! You will not be dissappointed with staying here! *Sidenote*Watch out for the deer! My brother in law was taking out the trash one night and about 6 went running around him.
Guest favorite

Home in Newburg

4.9 out of 5 average rating, 112 reviews

The River House, a Wicomico Beach Retreat

SabrinaRating, 5 stars3 weeks ago
This was our annual book club weekend and we had such a wonderful time. We spent cozy evenings by the fire. Enjoyed recommended places to visit and eat. I loved having my morning coffee on the dock and watching the sun come up. Thank you for sharing your home with our book club of 14 years!
Guest favorite

Home in Montross

4.99 out of 5 average rating, 144 reviews

Beach Please! River cottage w/private beach & dock

RobertRating, 5 stars1 month ago
Pictures don't do the place justice. The house itself is adorable, vintage cottage feel, well stocked. House also supplies so many activites....darts, pools table, tons of books, puzzles and board games, TV. The outside is the star though. Double decker back porches. Amazing view.....so worth getting up at sunrise!! Very peaceful neighborhood. Plus lots of water activities included.....canoe, kayak, paddle board, fishing poles, crab cage, fire pit, and large four person hot tub. This place is ideal for family get together or peaceful time away. We enjoyed our anniversary weekend away! Thank you.

Cottage rentals with a kayak

Guest favorite

Cottage in Lancaster

4.93 out of 5 average rating, 30 reviews

Christmas Cottage on the River

KelleyRating, 5 stars2 months ago
We absolutely loved Phillip’s incredibly charming and cozy cottage! The interior is gorgeous and the exterior waterfront view will take your breath away! We spent a lot of time fishing on the dock and loved eating our bountiful catch! Lots to explore nearby in the quaint small towns of the Northern Neck! Phillip was very quick to respond to my many questions and always offered local recommendations which we really appreciated! We did a quick run to Walmart to get firewood for the outdoor pit, bait and $9 camping chairs. The chairs made our dock fishing more comfortable than the built-in dock bench. My advice is run, don’t walk, to secure a reservation at this stunning waterfront oasis! We can’t wait to return! K Helms, Clifton, VA
Superhost

Cottage in Reedville

4.88 out of 5 average rating, 189 reviews

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

DonnaRating, 5 stars5 days ago
A wonderful Beautiful place. It is nicely decorated and roomy. Well worth the drive & the money. Would love to stay here again. Highly recommend.
Superhost

Cottage in Warsaw

4.94 out of 5 average rating, 108 reviews

Modern 2 Bdrm Cottage in Historic River Community

AliRating, 5 stars1 month ago
Renee’s home felt like a peaceful retreat. The country drive was serene and it brought you to a nestled community along the river. I loved the quaint church on your street too! I saw neighborhood dogs playing from Renee’s porch swing as I watched the sunset each evening. She left you kayaks and bikes to use while visiting too which was a nice touch. The home itself is exactly as pictured, if not better. My father said, “this is probably the nicest shower I’ll ever use in my lifetime”. Whether you’re looking for a cozy home to hunker down in or a place to watch your kids run around and play, this home is a great pick for everyone. Highly recommend! Thank you, Renee for being so responsive when I had questions and for opening your space to us. xx
Guest favorite

Cottage in Cambridge

4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

SarahRating, 5 stars3 weeks ago
My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!
Guest favorite

Cottage in Lusby

4.98 out of 5 average rating, 58 reviews

Stunning Secluded Luxury waterfront cottage!

CeciliaRating, 5 stars4 months ago
KJ we had an amazing time swimming, kayaking, fishing and crabbing!! We had a lovely dinner, kj had a large crab pot to cook the large bounty of crabs we caught. Was such a great and peaceful vacation. The house was pristine, loved drinking my coffee on the pouch and had a great time at night watching shooting stars by the campfire.
Guest favorite

Cottage in Hague

5 out of 5 average rating, 126 reviews

Potomac River cheerful cottage

JonRating, 5 stars2 weeks ago
The location was beautiful, the house was very well maintained and the host thought of everything to make the trip awesome. Highly recommend!
Guest favorite

Cottage in Kinsale

5 out of 5 average rating, 31 reviews

River + Beach Front Cottage 4 BR ADA Northern Neck

EmilyRating, 5 stars2 months ago
We had a wonderful long weekend here! The house is well-equipped and David was even able to secure fishing and crabbing gear so our two kids could try to catch dinner. It is a quiet street of cottages with friendly neighbors in a gorgeous location - the view is so calming. We enjoyed exploring the local area (love the coffee shop and brewery in Montross), kayaking, swimming, and relaxing on the big screened porch. A feature here that you don’t always have at the shore is a great sandy beach! Can’t wait to come back for another getaway.
Guest favorite

Cottage in Leonardtown

4.96 out of 5 average rating, 167 reviews

Beach Front and 'Perfectly Placed'

ShelleyRating, 5 stars3 weeks ago
Wonderful cottage for a restful and peaceful retreat! Gorgeous views, beautiful sunsets, well equipped, and cute decor. We loved coming out to the sitting room in the morning and watching the view. Perfect for families or even solo trips. My four year daughter had a magical time going down to the water and exploring. I loved seeing the awe on her face when she saw the sunset each evening. Will definitely recommend!

Cabin rentals with a kayak

Guest favorite

Cabin in Indian Head

4.97 out of 5 average rating, 29 reviews

*Private Waterfront Retreat w/3 Cabins Close to DC

JillRating, 5 stars3 weeks ago
Amazing water views from the main house and tiny house. The house was well stocked for cooking. We enjoyed having a grill and an Ooni oven for pizza night! Melanie was responsive and helpful.
Superhost

Cabin in Reedville

4.7 out of 5 average rating, 20 reviews

"Elderberries" Chesapeake Bayfront Cottage

MarkRating, 5 stars2 months ago
Had a great time at the Elderberries cottage! The views were spectacular, and you could take them in from the enclosed porch, the open deck, and even the living room. The entire setup was perfect for a vacation/remote work getaway, and the kitchen has everything you need. WiFi worked great, and the smart TV supported pretty much any streaming service you'd want. Rachel was friendly and super responsive; we hope to stay there again sometime.
Superhost

Cabin in Lancaster

4.88 out of 5 average rating, 51 reviews

Waterfront Log Home Retreat- Dock, Kayaks, Rest!

KelvinRating, 5 stars3 weeks ago
Great place to get away from the noise. Very peaceful and river view is amazing. Very nice amenities and great place to spend with your family and friends. Definitely recommend it!
Superhost

Cabin in Queenstown

4.89 out of 5 average rating, 19 reviews

Cozy Historic Cabin on the Water

CavanRating, 5 stars2 months ago
Great time, beautiful cabin and property!
Superhost

Cabin in Saint Michaels

4.75 out of 5 average rating, 80 reviews

Cottage #4 Chesapeake Blue down the drive way.

DavidRating, 5 stars4 months ago
I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.
Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 245 reviews

Peaceful Waterfront Retreat on The Bay

DavidRating, 5 stars3 weeks ago
Wow… what an amazing location and packed with so many details and so much character! We caught white perch off the private dock, rented a skiff down in Solomons to cruise the Patuxent, found a nice sized shark tooth fossil on the bay cliffs side, and caught some more perch using the cabin’s kayaks… all in all an amazing time even deep into cold November, I can’t wait to go back ASAP this is my new favorite place to escape!
Guest favorite

Cabin in Lusby

4.93 out of 5 average rating, 181 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

DanielleRating, 5 stars1 month ago
This was the perfect place for my DC-based family of 3 to have a getaway in nature. The sunrise over the lake, surrounded by autumn leaves, made us feel like we were living in a painting. My kiddo loved the swings (two on the porch and one inside!). The house is carefully curated and appointed with a fresh 70's vibe. It was very clean and incredibly cozy.
Guest favorite

Cabin in Montross

4.96 out of 5 average rating, 23 reviews

Camp Heron : Waterfront Cabin on the Potomac

JudithRating, 5 stars2 months ago
Just a stunning location! The bird watching was marvelous, every morning a pair of swans landed and swam around until dusk. Lots of blue herons, too. Good fishing right out of the back yard. The kitchen was very well appointed, good cookware, plates, cups, etc. bed were comfortable with really nice pillows. We spent most of our time around the fire pit or on the screened porch. A great place for relaxing!

Destinations to explore