Vacation rentals with a kayak in Talbot County

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Top-rated kayak rentals in Talbot County

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Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 41 reviews

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

Quiet waterfront cozy home w/ pvt pier, hot tub, kayaks, grill, massagechair & fire pit. Experience life on the river in a 2bedrm/1 bath-shower/3bed Retreat on a cove off the ChoptankRiver. About 15-20mins toHistoricCambridge/Restaurants/groceries. Easy day trips to St.Michaels/Tighlman/Oxford/Tubman; 75-90min drive to Ocean City/Rehoboth beach. Waterviews from beds. Relax in screened porch w/ waterviews. Watch sunrise/sunset in pvtpier/kayak/hottub. Bring fishing rods/crablines/baits-seasonal.

Guest favorite

Home in Preston

4.95 out of 5 average rating, 83 reviews

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or kayak, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Guest favorite

Home in Cambridge

4.96 out of 5 average rating, 111 reviews

Waterfront, Fabulous Home for Families with Pool!

If you were thinking of heading to the Eastern Shore, Casey's Porch is the place to go. Come and see for yourself. Bring your extended Family. Bring your friends. Please note spring mid-week rates! Kayaks and paddle boards and bikes await you at this beautiful home on Hudson Creek. Fish from the dock. Pull crabs from the creek. Walk down quiet country lanes. Sit around the fire pit. So many fun, outdoor things to do. Casey's Porch has it all. *4th Night Free is Winter Special

Guest favorite

Home in Stevensville

4.92 out of 5 average rating, 37 reviews

Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

Guest favorite

Barn in Queenstown

5 out of 5 average rating, 55 reviews

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

Guest favorite

Home in Chester

4.99 out of 5 average rating, 80 reviews

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

Superhost

Home in Annapolis

4.87 out of 5 average rating, 165 reviews

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay just 100ft away. Water views from nearly every room. 4 beds 4 full baths w/ luxury upgrades, new kitchen aid appliances, rustic leather sectional sofas that can sleep 4 more (14 total), outdoor grills, covered balconies, a new hot tub, kayaks. Access to community amenities incl community fishing/crabbing piers/beach/picnic area. Close to beautiful Thomas Point & Quiet Waters park. A unique escape for nature lovers !

Guest favorite

Home in Tilghman Island

5 out of 5 average rating, 10 reviews

Panoramic water views

Tilghman Island Point of View. Our Island is perfectly situated on the Maryland crab and oyster trail. Step back in time to a slower lifestyle and observe the waterman’s way of life. Enjoy our two-bedroom coastal cottage and Island attractions. Enjoy the bird’s eye view of the local waterman in and out of the harbor seeking the days catch. Walk or kayak the shoreline. Take a stroll or ride a bike to Island attractions including all restaurants and shops. Arrive by boat or car.

Guest favorite

Home in Easton

5 out of 5 average rating, 49 reviews

Tuckaway Cove Relaxing waterfront property

Tucked away on a beautiful, quiet cove off the Miles River, with a large yard for playing, a private pool & dock, & kayaks for water fun, Tuckaway Cove provides all the perfect ingredients for a relaxing, memorable family vacation! The home is fresh & bright, comfortable & spacious with a nautical theme throughout. The location is private, but conveniently located between Easton and St Michaels, close to everything you need! Licensed by Talbot County, MD #ST-851-MIL 2019

Guest favorite

Cottage in Saint Michaels

4.97 out of 5 average rating, 158 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 136 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 96 reviews

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!