
Holiday rentals with a kayak in Maryland
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Maryland
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for kayak rentals in Maryland
House rentals with a kayak

Waterfront Getaway with Dock
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.

Luxury 5BR: Beach, GameRm, Arcade, Theater
This was our second year in a row visiting Julya’s place! Our family loved it so much last year we booked as soon as we could for this season. The house was just as beautiful as we remembered, the kids even said it felt like home the second day. All the thoughtful things included are so nice (blackout shades for the kids, all the kids kitchen stuff, extras for all usable items, beach items). And we love the location! Easy to get to activities, we very much enjoyed the marine museum, the Imaginarium, fishing on the shea-d-lady, and sailing with Sail Solomons. Island Hideway was huge hit with the whole family for dinner. The house is an easy walk to the beach and the view is so cool, feels like a beach treehouse. Will hopefully be back again next year (if not at the end of this season!) 😁 Thank you Julya!!

Cove Point Beach Cabin
Came back for a third visit and had a lovely time at this peaceful retreat.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
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!

Newly Renovated Modern 3 bed 2 bath Water Front
The River House was phenomenal, a beautifully furnished place with large riverfront lawn and private boat launch. Exceptionally clean and well-stocked with everything you could think of for a comfy stay (fluffy towels, extra paper products, cleaning supplies, blankets, tons of pillows). Kitchen is as beautiful as the photos, and amply stocked with everything from ziplocs to pyrex to measuring cups and baking tools. The kayaks and canoe were easy to access and use. Easy place to paddle in a calm and quiet tributary. Highly recommend Lindy’s seafood a mile away. Host has compiled a guidebook with lots of local business recs and info. You will not be disappointed with a stay at this awesome retreat.

Waterfront Farmhouse Meets Modern Luxury
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

3 bedroom/2.5 bath Smith Island bungalow with dock
Wonderful accommodations for a relaxing visit to a beautiful island!

Welcome to Heron House! Annapolis Waterfront Oasis
We had the best time enjoying Jody and Gail's beautiful home! The views were incredible, it was so peaceful, and the house had every amenity we could have wanted. A highlight was kayaking and swimming in the cove right to the side of the home. We cant wait to come back!
Cottage rentals with a kayak

Chesapeake Bay Cottage
Lovely stay on the water! Mini beach is an added bonus. Great restaurants nearby!

Where Eagles Soar *Stunning Waterfront Views*
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.

Levering Creek Cottage with Private Dock
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!

Charming Waterfront Cottage with Sunset Views
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 !

Weems Creek Cottage, Annapolis Waterfront
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!

Ft. Smallwood Overlook. Waterfront with Kayaks!
Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
I think this is my 5th time staying there. Always thinking of my return visit before even leaving!

Waterfront Chesapeake Bay Sunrises w/Private PIER!
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!
Cabin rentals with a kayak

*Private Waterfront Retreat w/3 Cabins Close to DC
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!

True St. Michaels 6 Acre Waterfront w/heated pool
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.

Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTDOOR MOVIE EXPERIENCE*HOT TUB*1.8mi to WISP*WORK SPACES*wood CRIB!
We had a fabulous week at the mad men house. There were plenty of places to get some personal quiet time and the sleeping arrangements were perfect for our group. Stay here again if we return to deep Creek Lake.

Large Cabin w/ RiverView&Hot Tub
We had a great stay at this cabin—very clean, well-stocked, and comfortable. The kitchen, bathrooms, and laundry were all in excellent shape and stocked well, and the washer/dryer was high quality. Beds and linens were comfortable, and the hot tub was a relaxing bonus. Appreciated the availability of streaming TV. Beautiful, peaceful setting. Only wish the patio furniture had been a bit more usable. Overall, highly recommend!

Pizza Friday
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.

Whispering Pines Cabin Pond Views/Access
Such a beautiful cabin. Very peaceful. Loved the hot tub area and the fireplace area!

Deep Creek Aframe : Lake View, Dock slip, Hot Tub
Absolutely loved our stay at the A-frame cabin at Deep Creek! The space is even more spacious and beautiful in person. It perfectly blends cozy cabin vibes with modern touches. The view is absolutely breathtaking. Whether you’re sipping coffee in the morning or watching the sunset, it’s impossible not to feel relaxed and inspired. The cabin is full of thoughtful little details that really make you feel cared for. From the decor to the layout to the small touches you discover throughout the space, it’s clear a lot of love and intention went into designing this retreat. One thing to note: the driveway up to the cabin is pretty steep, so just be prepared for that, especially in icy or rainy weather. But once you’re up there, it’s totally worth it. A perfect getaway that we’re already dreaming of returning to.

Cabin on the Creek ~ Kayaks and Fire Pit
This is may be my favorite airbnb that I've ever stayed at. The house was so well stocked--not just with the essentials but with all kinds of wonderful extras (soap, shampoo, tea, coffee, etc.) and the kitchen was not only well stocked but the knives were actually sharp and the pans were great quality etc. The area was beautiful, and we thoroughly enjoyed the fire pit (fire wood was well stocked). The dock was lovely and the kayaks in great condition. We enjoyed several kayaking ventures on the creek, which was beautiful and quiet. It felt like we had the creek all to ourselves!
Destinations to explore
- Rentals with a washing machine and dryer Maryland
- Aparthotel rentals Maryland
- Apartment rentals Maryland
- Rentals with beach access Maryland
- Rentals with outdoor seating Maryland
- Rentals with an EV charger Maryland
- Townhouse rentals Maryland
- Rentals with a firepit Maryland
- Villa rentals Maryland
- Rentals with a fireplace Maryland
- Rentals with pools Maryland
- Rentals with a sauna Maryland
- Waterfront rentals Maryland
- Family-friendly rentals Maryland
- Chalet rentals Maryland
- Rentals with lake access Maryland
- Smoking-friendly rentals Maryland
- Ski-in/ski-out rentals Maryland
- Farm stay rentals Maryland
- Rentals with breakfast Maryland
- Family-friendly rentals Maryland
- Lakehouse rentals Maryland
- Beach apartment rentals Maryland
- House rentals Maryland
- Mansion rentals Maryland
- Bungalow rentals Maryland
- Hotel rentals Maryland
- Rentals with an accessible-height bed Maryland
- Beachfront rentals Maryland
- Boutique hotel rentals Maryland
- Rentals with a cinema Maryland
- Guest house rentals Maryland
- Tiny house rentals Maryland
- Cabin rentals Maryland
- Private suite rentals Maryland
- Rentals with an accessible-height toilet Maryland
- Pet-friendly rentals Maryland
- Flat rentals Maryland
- Cottage rentals Maryland
- Beach house rentals Maryland
- Rentals with a patio Maryland
- Fitness-friendly rentals Maryland
- Bed and breakfasts Maryland
- Rentals with a hot tub Maryland
- Rentals with a kayak United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do Maryland
- Sports activities Maryland
- Nature and outdoors Maryland
- Tours Maryland
- Art and culture Maryland
- Sightseeing Maryland
- Food and drink Maryland
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Sports activities United States
- Nature and outdoors United States
- Wellness United States
- Art and culture United States
- Tours United States
- Food and drink United States