Vacation rentals with a kayak in Maryland

Find and book unique kayak rentals on Airbnb

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Popular amenities for Maryland kayak rentals

House rentals with a kayak

Guest favorite
Home in Woolford
4.93 out of 5 average rating, 145 reviews

Waterfront Getaway with Dock

TysheraRating, 5 stars4 weeks ago
Went to location as a family get-away. The views were breathtaking, who knew we would find such peace so close to home. Literally sat on the couch and stared outside for hours. The home was small enough to enjoy each other's company but large enough to allow everyone the time and space to do their own thing. The price was more than reasonable and we can't wait to return.
Guest favorite
Home in Preston
4.96 out of 5 average rating, 93 reviews

River House on the Choptank

MichelleRating, 5 stars3 weeks ago
We really enjoyed our stay at Steven’s River house on the Choptank River. I appreciated the beautiful, peaceful atmosphere while sitting on the back deck! The home is clean, open and very comfortable. Steven was always quick to answer emails and we would love to stay again should we come back to the area!
Guest favorite
Home in Chestertown
4.93 out of 5 average rating, 43 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

ChristineRating, 5 stars3 weeks ago
Ina was a great communicator - from initial contact, instructions for the house, to checkout! She couldn’t have been better. She was quick to respond and very helpful, which made everything super easy. The house had such an amazing view! Our water-loving dog found the river within 5 mins of getting out of the car!! Great amenities (incl. kayaks, life vests (even for the pup!), well stocked kitchen, bed linens, comfy beds and furniture, nicely decorated, and clean)! It was an easy ride to town. We went to get a bit of a respite from our busy lives for a few days in the off season, and the surroundings were just what we needed. One downside was that the utilities (refrigerator and heat) are rather loud when they turn on, so if you’re a light sleeper, you may be bothered. We were awakened a few times, but the rest of the positives made up for it!! Great spot!
Guest favorite
Home in Deale
4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

CourtneyRating, 5 stars3 weeks ago
This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.
Guest favorite
Home in Middle River
4.95 out of 5 average rating, 39 reviews

Waterfront Home with Private Beach, Stunning Views

EvanRating, 5 stars4 days ago
Great place, we had a family get together and we had a very peaceful weekend. There were so many places to hang out between the porches and dock-side area, big living room and huge dining room table. Very tranquil, I was thoroughly pleased with the home!
Guest favorite
Home in Westover
5 out of 5 average rating, 16 reviews

Rumbley Retreat

ChadRating, 5 stars2 months ago
Came down for a duck hunting trip! The place was perfect! Very clean and cozy! Hope the owner was very attentive and quick to respond with any questions! If in the area again I will definitely book again!
Superhost
Home in Mechanicsville
4.95 out of 5 average rating, 75 reviews

Stylish waterfront retreat, 1 hr to DC

TinaRating, 5 stars2 months ago
Great house. Clean, clutter-free, and nicely furnished. Amazing hosts. Lovely location. Clear instructions. It was just a lovely time overall. Thanks so much for hosting us.
Top guest favorite
Home in North East
4.96 out of 5 average rating, 46 reviews

Boho River Cottage

StaceyRating, 5 stars5 days ago
Our stay at Cece's Boho Cottage was excellent. It started with an egg hunt around the yard for my boys along with some sweet treats for all to enjoy. Cece gave amazing restaurant suggestions along with local hikes and shops. If you happen to forget something, Cece thought of it! We loved morning coffee on the back porch with the rising sun, comfy beds, and enough space to spread out. Thank you for sharing your adorable cottage with us! We are already trying to plan a trip back!

Cottage rentals with a kayak

Guest favorite
Cottage in Charlestown
4.91 out of 5 average rating, 67 reviews

Charlestown Cottage at Cattail Bend

CaitRating, 5 stars4 weeks ago
The cottage was exactly as described and everything we could have wanted! I have zero critiques—Laura thought of everything.
Top guest favorite
Cottage in Annapolis
4.98 out of 5 average rating, 112 reviews

Weems Creek Cottage, Annapolis Waterfront

BenjaminRating, 5 stars2 weeks ago
What a beautiful off the beaten path place to stay. You are within walking distance of restaurants, coffee, and grocery. But feel like you’re miles away. That’s the effect the cabin has on you. There is a beautiful waterfront that you can enjoy from just about every area of the home. Jim was more than helpful. He really went above and beyond over most host. We would definitely Stay again. It’s the perfect spot if you need to relax.
Guest favorite
Cottage in Charlestown
4.96 out of 5 average rating, 162 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

JulieRating, 5 stars3 days ago
A little slice of heaven! The most beautiful and peaceful AirBnB we have stayed at. We didn’t turn the TV on once. Everything was so perfectly beautiful from inside to outside. The kayaks and hot tub are such a highlight and the beach is an awesome sea glass hunting ground. We will be back soon.
Guest favorite
Cottage in Pasadena
4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars4 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 !
Top guest favorite
Cottage in East New Market
4.95 out of 5 average rating, 61 reviews

Cottage on Cabin Creek

LornaRating, 5 stars2 months ago
My husband and I traveled here for a night away from our children and work responsibilities. We were looking for some place that was private and on the water. This place was both and it did not disappoint! The loft was cozy and spacious and we loved looking out the windows at the water and rain. It was very clean and there were plenty of towels and blankets and other special touches. Janelle communicated with us ahead of time to make sure she was ready for our arrival and she was kind and responsive throughout the process. We also found it easy to get into Easton for dinner at The Stewart, which was a treat, and then return back to the cabin. I would stay here again in a heartbeat -- but hopefully for longer next time.
Superhost
Cottage in Tall Timbers
4.89 out of 5 average rating, 119 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

KarenRating, 5 stars1 month ago
A beautiful home with space for several people, close to the water and surrounded by beautiful pine trees. Clean and tidy with a coastal charm, pet friendly is an extra bonus! Owners were very supportive and communicative.
Guest favorite
Cottage in Leonardtown
4.96 out of 5 average rating, 182 reviews

Beach Front and 'Perfectly Placed'

BenjaminRating, 5 stars1 week ago
It is the perfect location for a relaxed getaway. Several lovely state parks within a short distance. The space is well equipped and comfortable with magical sunsets over the Potomac. Theresa is super responsive.
Guest favorite
Cottage in Wittman
4.89 out of 5 average rating, 159 reviews

"Wittman Cottage"

JeanRating, 5 stars3 weeks ago
This was my 2nd visit to Lace’s home and would return again! I greatly enjoyed the private, quiet and peaceful surroundings, with views of Harris Creek from both the front and rear of the home, yet just a short drive to the shops & restaurants of St. Michaels and only 30 minutes to Easton. My favorite part? The huge screened in porch with lots of comfy furniture facing the water. With a dock, fire pit, outdoor eating spaces & included kayaks you, relatives & friends will enjoy yourselves at this spacious home.

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 stars3 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 favorite
Cabin in McHenry
4.98 out of 5 average rating, 132 reviews

Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTDOOR MOVIE EXPERIENCE*HOT TUB*1.8mi to WISP*WORK SPACES*wood CRIB!

KellyRating, 5 stars6 days ago
We had the BEST time at Mad Men Lake House. We had kids with us aged 6-18, and they were never bored. Between the pool and ping-pong, swings, air hockey, and the other fun games, they were always having a blast! The kayaks and life vests were perfect, with plenty of options to take everyone out on the lake. Our dogs also loved having a completely closed off upper deck to lounge on with no fear of them going on an unexpected adventure outside. We enjoyed local hiking spots as well. Wish we could spend more time there! Thank you to Rebecca and family for thinking of all of the little details, from decor to amenities to make this an unforgettable family vacation.
Superhost
Cabin in Queenstown
4.9 out of 5 average rating, 20 reviews

Warm and Cozy Historic Cabin on the Water

jeffRating, 5 stars1 month ago
Such a cool cabin. Wish we could have stayed longer.
Superhost
Cabin in Elkton
4.74 out of 5 average rating, 47 reviews

Large Cabin w/ RiverView&Hot Tub

KatieRating, 5 stars2 months ago
This cottage was the perfect respite for my family. The big panoramic window that looked out over the water was perfect. The house was so comfortable and the hosts were very responsive. Highly recommend a stay here. There isn’t a lot to do in the immediate area, but the university of Delaware was 20 minutes away and Baltimore an hour south. It was a perfect house for a long weekend getaway.
Guest favorite
Cabin in Accident
4.95 out of 5 average rating, 65 reviews

Cozy Chalet @ Pond's Edge - Comcast WiFi -Wisp/DCL

ChrisRating, 5 stars1 month ago
The house amazing and beautiful especially in the daytime. There was some trouble finding the house, but check it was a breeze once it was located. Highly recommend.
Top guest favorite
Cabin in Accident
4.98 out of 5 average rating, 97 reviews

Whispering Pines Cabin Pond Views/Access

HannahRating, 5 stars3 weeks ago
Jesse was a fantastic host! We had a wonderful time connecting with friends! The property was beautiful we spent lots of time outside, by the fire, pond, and playing yard game! Thank you for sharing your home!
Guest favorite
Cabin in Lusby
4.9 out of 5 average rating, 258 reviews

Peaceful Waterfront Retreat on The Bay

DonnaRating, 5 stars3 days ago
A fair and open spaced home. Free of clutter. Many updated electronics I didn't expect. Only drawback was the microwave. It had a lagging door switch that locked when it was ready. If your impatience, it would test your nerves. A shower that was plenty hot and spacious. Loved the size of the home and location, I want to rent this again.
Guest favorite
Cabin in Oakland
4.97 out of 5 average rating, 30 reviews

Deep Creek Aframe : Lake View, Dock slip, Hot Tub

BriannahRating, 5 stars2 months ago
Rented this cabin for my birthday and it was amazing! My friends and I loved everything about their place! The food around the area is amazing and we also went skiing one of the days. If anyone would ask any of us we would definitely recommend this cabin. We’ve all talked about coming back next year we just loved it so much!!

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