Holiday rentals with a kayak in Kent Island

Find and book unique kayak rentals on Airbnb

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Popular amenities for Kent Island kayak rentals

Holiday House Rentals with a Kayak

Top Guest favourite
Home in Woolford
4.93 out of 5 average rating, 151 reviews

Waterfront Getaway with Dock

SarahRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Shady Side
4.96 out of 5 average rating, 106 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

NicholasRating, 5 stars7 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.
Top Guest favourite
Home in Lusby
4.99 out of 5 average rating, 302 reviews

Cove Point Beach Cabin

CassieRating, 5 stars2 weeks ago
Came back for a third visit and had a lovely time at this peaceful retreat.
Guest favourite
Home in Cambridge
4.97 out of 5 average rating, 115 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars2 weeks ago
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.
Top Guest favourite
Home in Woolford
5 out of 5 average rating, 221 reviews

Newly Renovated Modern 3 bed 2 bath Water Front

HilaryRating, 5 stars3 weeks ago
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.
Superhost
Home in Shady Side
4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

AshleyRating, 5 stars8 months ago
We had a wonderful time during our visit. The peaceful environment on the water was just what our group needed. Thank you!
Top Guest favourite
Home in Deale
4.99 out of 5 average rating, 145 reviews

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

LauraRating, 5 stars3 days ago
Natalie’s place was just like the pictures. Everything was clean and well stocked for our stay of 6 adults. The sunsets were beautiful from the dock and the kayaks were a definite bonus! We enjoyed time outside on the dock, deck, and in the hot tub! The beds were very comfortable and our stay was great!
Guest favourite
Home in Deale
4.98 out of 5 average rating, 110 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

RobertRating, 5 stars1 week ago
We were looking for a relaxing getaway, and saw an opening at this property. Booked for two weeks, and thoroughly enjoyed our stay… Very large property on the water.. fields and wooded, very quiet, very peaceful. A long dock with a great view of the bay. Supermarket nearby, a couple of very good restaurants. Richard had the house stocked with literally everything needed…. All we provided were groceries! Ducks, geese, herons, ospreys, egrets, songbirds, and several deer provided daily entertainment. Communication was excellent, responses just about instant. Got a chance to meet Mark, who provided some interesting history of this family property. To sum it up, highly recommend!!!

Cottages with a kayak

Superhost
Cottage in Annapolis
4.85 out of 5 average rating, 87 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

AliRating, 5 stars4 days ago
He was a great host and the neighborhood was perfect for us with little kids ! We had a wonderful weekend away!
Top Guest favourite
Cottage in Oxford
5 out of 5 average rating, 17 reviews

Sailor's Cottage - Private Waterfront

ChristopherRating, 5 stars4 days ago
We recently stayed at this beautiful Airbnb tucked away on a secluded property in Oxford, and it was exactly the reset our family needed. The house was spotless, cozy, and surrounded by nature—offering the kind of quiet you don’t realize you’ve been craving until you hear it. What truly made this stay exceptional were the hosts. We arrived by boat at a nearby marina, and due to our boat’s deep draft, they picked us up to bring us to the house. That extra effort made all the difference, especially with a group that included kids and family coming in from different ends. The home felt like a retreat—private, peaceful, and welcoming. It gave us a much-needed chance to reconnect, recharge, and create some lasting memories. We’d absolutely stay again and recommend this home to anyone looking for an escape from the hustle without sacrificing comfort or kindness.
Guest favourite
Cottage in Deale
4.96 out of 5 average rating, 160 reviews

Chesapeake Bay Cottage

MargaretRating, 5 stars1 month ago
Lovely stay on the water! Mini beach is an added bonus. Great restaurants nearby!
Guest favourite
Cottage in Cambridge
4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

SarahRating, 5 stars6 months 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!
Top Guest favourite
Cottage in Annapolis
4.98 out of 5 average rating, 115 reviews

Weems Creek Cottage, Annapolis Waterfront

AmyRating, 5 stars1 week ago
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!
Guest favourite
Cottage in Pasadena
4.97 out of 5 average rating, 175 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

EmilyRating, 5 stars4 weeks ago
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 !
Top Guest favourite
Cottage in East New Market
4.95 out of 5 average rating, 65 reviews

Cottage on Cabin Creek

MattRating, 5 stars1 week ago
Beautiful private hidden gem on the water, perfect place to escape for a weekend.
Guest favourite
Cottage in Lusby
4.89 out of 5 average rating, 44 reviews

Hot Tub Hideaway by Shark Tooth Shores

RebeccaRating, 5 stars1 month ago
Surrounded by trees and the sound of waves- perfect place to relax & unwind. Quick but steep hike to the secret beach. Cool spot and more shell than I expected. Kyli was a responsive host, answered all my questions. Also, recommended Island Hideaway for dinner and it was amazing. Homemade pasta and desserts made in house daily. Great views and delicious foods & drinks.

Cabin rentals with a kayak

Guest favourite
Cabin in Saint Michaels
4.99 out of 5 average rating, 112 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

KateRating, 5 stars2 weeks ago
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.
Superhost
Cabin in Queenstown
4.9 out of 5 average rating, 21 reviews

Cozy Historic Cabin on the Water

KrystalRating, 5 stars3 weeks ago
Staying at Shawna and Keith's cabin was a wonderful experience. Peaceful and serene, it was relaxing just to wake up in this private oasis. Shawna and Keith were very friendly and easy to get in touch with if we had any questions. They even provided items for some of the activities we decided to try while staying there. The cabin was clean, quaint, quiet, well-equipped; and looked exactly as described. We would definitely return for another weekend getaway! Thanks again!
Guest favourite
Cabin in Saint Michaels
4.75 out of 5 average rating, 81 reviews

Cottage #4 Chesapeake Blue down the drive way.

DavidRating, 5 stars10 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 favourite
Cabin in Lusby
4.9 out of 5 average rating, 267 reviews

Peaceful Waterfront Retreat on The Bay

SarahRating, 5 stars1 week ago
It’s our second stay at Camp Maier and we are already planning to come back. As soon as we step in, we feel calmed by the view and the comfortable space. The place has had a fresh coat of paint since we were here last, and we appreciated the kitchen upgrades too. We loved pizza at Cryptic Pizza in Solomons Island and a walk with dogs at Flag Ponds nature park. Even found a small fossilized shark tooth! A magical time. Thank you.
Cabin in Saint Michaels
5 out of 5 average rating, 4 reviews

Serene Waterfront Retreat – Chesapeake Bay Escape

JamesRating, 5 stars1 week ago
Elizabeth's house was perfect for our weekend stay in St. Michael's. The house sits right on the water about a 5 minute drive from the center of town. It was the perfect home base for the Ironman event we were attending in Cambridge. Elizabeth was incredibly responsive and provided thoughtful recommendations for our stay. If we are in the area again we will certainly stay again.
Guest favourite
Cabin in Worton
4.94 out of 5 average rating, 93 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

MonicaRating, 5 stars4 days ago
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!
Top Guest favourite
Cabin in Lusby
4.98 out of 5 average rating, 90 reviews

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

LaurenRating, 5 stars2 weeks ago
We stayed at Julie’s home with a group of friends and our families and had a wonderful time. The lakefront setting was incredibly relaxing—we found ourselves rarely leaving the property because it had everything we needed. From soaking in the hot tub to enjoying the game room, there was something for everyone. The kids loved having space to run around in the basement, while the adults enjoyed peaceful mornings and evenings on the screened-in porch. Julie was very responsive and answered all of our questions quickly, which made the entire experience seamless. We would absolutely stay here again!
Superhost
Cabin in Lusby
4.76 out of 5 average rating, 21 reviews

Covenant Cove (Cove Point Beach)

NiccoleRating, 5 stars1 week ago
We absolutely loved this place. It was a short drive to the bay and certainly worth it. The cottage was secluded enough from the neighbors and we could hear the waves with the windows open. The beach was a very short walk from the cottage and was also very private. We spent a good chunk of our time finding sharks teeth and relaxing on the porch. Grocery stores and gas stations are also fairly close. We even booked our stay for next year already.

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