Vacation rentals with a kayak in Maryland

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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 stars1 month 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, 94 reviews

River House on the Choptank

JimRating, 5 stars4 days ago
Great place! very charming, relaxing, peaceful! No problem feeling right at home. We would stay here again in a heartbeat. Here are a few pointers for those who are planning to stay here: - Its pretty far from grocery / convenience stores - about 30 minutes one way. Do your homework before you get to the place, and try to get all the supplies you will need ahead of time. - The bathrooms are Jack and Jill's so if you're going to a big event - in our case a wedding, make sure that you have a bathroom plan in place as you will have to make sure both sides of the door are ready for who is going to take their time first. No biggie if you're used to j&j bathroom arrangements. I totally recommend this place for a group of 4 - 6 who want together time to relax!
Guest favorite
Home in Chestertown
4.93 out of 5 average rating, 43 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

ChristineRating, 5 stars1 month 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 stars1 month 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 stars1 week 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 stars3 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 stars3 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 stars1 week 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, 68 reviews

Charlestown Cottage at Cattail Bend

MarillaRating, 5 stars4 days ago
Cute place in a cool area! Perfect size for 4 people, loved walking to the nearby beach. Beds were comfy, kitchen was well-stocked for a small space. We enjoyed sitting on the screened-in porch watching the creek ebb and rise with the tide. There's a fire station next door, so we did hear loud sirens. But otherwise peaceful.
Top guest favorite
Cottage in Annapolis
4.98 out of 5 average rating, 112 reviews

Weems Creek Cottage, Annapolis Waterfront

BenjaminRating, 5 stars3 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, 164 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Joseph & TracyRating, 5 stars6 days ago
The property is beautiful, its just like the pictures. The location is peaceful and quite. Its a perfect spot to just to relax and reconnect. Can't say enough good things about the cottage. Clean, Bed was nice, view was amazing, Hot tub, kayaks, plenty of firewood for a beach fire. During our stay we went to main street in North East it was about a 7 minute drive. It was a nice little town to walk. Chesapeake Coffee Co for a breakfast sandwich and a coffee. We had lunch at Woody's crab shack. Ordered in pizza from Bella Pizza, Went to Nauti Goose. I was underwhelmed at all restaurants and by all meals. If we come back again, I'd get groceries to cook, there is a grill to use (we didn't) and stay in, just take in the view and enjoy the peaceful waves. We would defiantly recommend and hopefully be back again soon.
Guest favorite
Cottage in Pasadena
4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars5 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, 62 reviews

Cottage on Cabin Creek

JenniferRating, 5 stars3 weeks ago
We would highly recommend this peaceful and relaxing cottage. We especially loved the views, the dock for fishing, & the views from the bedroom. Janelle was very helpful with places to visit as well as working out an issue that came up at the property. She was quick to respond & made every effort to make sure we were comfortable. Would definitely stay here again! 😊
Guest favorite
Cottage in Tall Timbers
4.89 out of 5 average rating, 120 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

JenniferRating, 5 stars1 week ago
This was our second stay with Bob and Lolly in Tall Timbers, and it did not disappoint! Immersed in books and history, this quaint cottage was the perfect getaway. We are looking forward to our next visit!
Guest favorite
Cottage in Leonardtown
4.96 out of 5 average rating, 183 reviews

Beach Front and 'Perfectly Placed'

AmberRating, 5 starstoday
Teresa’s home was charming and relaxing. That’s the best words for it. The outside space was so peaceful. We absolutely loved the kayaks, making a fire, sitting outside listening to the waves, the beautiful sunset on the water, the quiet location. Very clean space. Had everything we needed. Coffee station was very nice. Comfortable beds. My girls enjoyed the bunk beds. Loved the deep bathtub. Very relaxing! Very nice washer and dryer with all the cleaning supplies you need, kitchen utensils, plates, glassware, pots, pans. The neighbors have the absolute sweetest most gorgeous Great Danes I’ve ever seen. They came over to say hi when I built a fire. Super amazing people to speak to. So kind and down to earth. Town is a little ways off. I’m so used to being in a city and a coffee shop being a mile if I wanted an expresso. I would suggest stopping at the market and picking up everything you need in advance. Fridge is spacious so it’ll fit whatever you bring. Enjoyed it so much!
Guest favorite
Cottage in Wittman
4.89 out of 5 average rating, 159 reviews

"Wittman Cottage"

JeanRating, 5 stars4 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 Saint Michaels
4.99 out of 5 average rating, 108 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

KyleRating, 5 stars3 months ago
Marissa’s home was beautiful and had everything we needed - plus some. Plenty of clean/comfort space and restrooms for our party of 6. We had such a relaxing, warm stay during a snowy January weekend - even smores! Marissa was always responsive and provided suggestions for shopping and dining in St. Michael’s. It was lovely all the way around! Highly recommend this home and working with these owners. Top notch!
Guest favorite
Cabin in McHenry
4.98 out of 5 average rating, 133 reviews

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

KellyRating, 5 stars1 week 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
4.73 out of 5 average rating, 48 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, 66 reviews

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

SusanRating, 5 stars2 weeks ago
We loved at our stay at this beautiful cabin! The pond in the backyard was the highlight — it led to beautiful views and a nice morning walk each day. The home was so clean and had everything we could possibly need. We had our kids with us and there were board games, puzzles and plenty of toys that they were so excited about. The kitchen was fully stocked and there were plenty of blankets in all the rooms (which we needed since it ended up being SO cold). We were expecting a nice, warm spring break getaway, but it ended up being very cold and this cabin proved to be perfect for the cold (and I bet it would’ve been even more fun in warm weather). We made s’mores in front of the beautiful pond one of the evenings. Overall, we loved our stay here and would definitely stay here again. Ken was also very accommodating and incredibly responsive — he gave us plenty of local recommendations too!
Guest favorite
Cabin in Accident
4.98 out of 5 average rating, 97 reviews

Whispering Pines Cabin Pond Views/Access

HannahRating, 5 stars1 month 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, 259 reviews

Peaceful Waterfront Retreat on The Bay

DonnaRating, 5 stars1 week 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.

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