Holiday rentals with a kayak in Kent Island

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Top-rated rentals with kayak in Kent Island

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Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 154 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Superhost

Campervan/Motorhome in Sparrows Point

4.85 out of 5 average rating, 150 reviews

Cozy Camper, 2010 Brookstone RV - Waterfront

38 foot Fifth Wheel RV located at marina. Fully equipped kitchen, 1 bath and 1 bedroom with comfy King bed. Living space includes dinette with 4 chairs, sofa w/ full size air mattress and two recliners set up in front of a 42" flat screen TV. Heat and air provide the perfect accommodations no matter the weather. Enjoy sitting by the fire pit or explore the Bay on one of our two Kayaks. A stone's throw from Trade Point Atlantic, Key Bridge work site. Just 15-20 minutes to downtown Baltimore.

Top guest favourite

Home in Cambridge

4.99 out of 5 average rating, 171 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Superhost

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of May 1st.... "Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take our kayaks to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acres in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home.

Guest favourite

Home in Deale

4.98 out of 5 average rating, 106 reviews

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

3 Bedroom, 2 Bath Waterfront Paradise. This rustic rambler on Broadwater Creek in Churchton, MD, is a family vacation dream. A compound spanning 8 acres with over 700 feet of Waterfront will allow you to fish, crab, paddleboard, kayak, and enjoy the waterfront dream. Located near the small quaint waterman town of Deale, MD, you may never want to leave this relaxing area with direct access to the Chesapeake Bay. Brand new 140ft pier with views straight out to the bay, crabbing, and fishing!

Guest favourite

Home in Saint Leonard

4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Guest favourite

Home in Deale

4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views, & wildlife. Hidden but close to services. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Guest favourite

Home in Riviera Beach

4.95 out of 5 average rating, 137 reviews

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 3 Bathroom .one bed on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

Guest favourite

Home in Shady Side

4.96 out of 5 average rating, 105 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Located 35 minutes from Annapolis and 45 minutes from Washington DC, Shady Side is a quaint town. This waterfront home is perfect for families or small groups looking to enjoy a relaxing getaway on the Chesapeake Bay. Enjoy the large wrap-around screened in porch and private pier with ladder for easy access for swimming. Large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 min away in Parish Creek. Listed for 8 people max but contact us for approval of 1-2 more.

Guest favourite

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Top guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 221 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Guest favourite

Home in Cambridge

4.98 out of 5 average rating, 126 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!