Vacation rentals with a kayak in Talbot County

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Top-rated kayak rentals in Talbot County

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Cambridge

4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

Relax and unwind at our 2 acre waterfront cottage. Enjoy the private dock, kayaks, fire pit, front porch, or back deck! Known for excellent fishing, crabbing, hunting, and boating. The tiny city of Cambridge is rich with history, has maintained its charm and adds tasteful local shops/eats. Public boat ramp 3 miles away Hyatt Regency Golf Course and Spa Resort (15min) Adorable Easton/ St. Michaels (30min) Nearby Blackwater National Wildlife Refuge is 28,000 acres ideal for the outdoors man/woman

Top guest favorite

Home in Cambridge

4.98 out of 5 average rating, 45 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.

Top guest favorite

Guesthouse in Cambridge

5 out of 5 average rating, 14 reviews

High Water Guest House

Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of historic High Street and adjacent to the city marina. Walk to downtown for shopping and dining. Take advantage of having a front row seat to the finish line of Ironman Maryland. Beach, pier and large yard made available for your use. Bring your kayak, paddleboard, or boat and enjoy all Cambridge has to offer or just sit on the end of the pier to watch the sunrise or sunset.

Superhost

Cottage in Saint Michaels

4.84 out of 5 average rating, 31 reviews

Cottage #8 Herons Nest Lg 2 rooms Under Main House

OPEN March 25th to Nov 1st. every year. Herons Nest no 8 is located under main house, consist of full Kitchen, dining table, 1 queen size bed in separate bedroom, Living room Full size Futon open to a bed, 2 large sleeper recliners. Please call Jaimie upon arrival. No pets allowed! We no longer provide bed linens, Coffee, sugar or creams. or Towels. Boats are rentals! room tax 4% due on arrival , 6% Abb collects please Bring waters . Boat info below. If need air mattress can bring.

Superhost

Home in Royal Oak

5 out of 5 average rating, 15 reviews

Waterfront Cottage Retreat on 18 Acre Farm, Pool

Our newly renovated point cottage is nestled on an 18 acre waterfront private retreat with access to a swimming pool, gym, tennis court, dock & more! This cottage features a private porch to enjoy the sunset, fully-equipped kitchen and laundry in unit. The cottage shares the grounds with a few other of our private cottages. Guests also have access to kayaks, fishing equipment, the fire pit, ice cream shop & library! Quiet and remote but very close to both Easton and Saint Michaels.

Top guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 160 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.

Top guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 140 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

Superhost

Home in Annapolis

4.87 out of 5 average rating, 176 reviews

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay just 100ft away. Water views from most rooms plus treehouse vibes. 4 bed 4 full bath. Custom luxury upgrades, new kitchen aid appliances, rustic leather sectional sofas can sleep 4 more (14 total), outdoor grills, covered balconies, new hot tub, kayaks. Access to 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 Cambridge

4.96 out of 5 average rating, 112 reviews

Gorgeous, waterfront home. Perfect for Families.

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. 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. First Floor bedroom, also.

Superhost

Home in Cambridge

4.9 out of 5 average rating, 107 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!

Top guest favorite

Home in Cambridge

5 out of 5 average rating, 34 reviews

Serene getaway with great waterfront views!

Serene getaway with great waterfront views, private dock, and expansive deck. Located 10 minutes from Cambridge, MD, this home offers small groups and families a unique location with waterfront views throughout the house, updated spacious kitchen, kayaks, large back yard, grill for barbecue, and large dining and living rooms. Perfect for a quiet getaway to enjoy expansive views of the Choptank River at the mouth of Chesapeake Bay.

Superhost

Home in Tilghman Island

5 out of 5 average rating, 4 reviews

Time Stands Still At the Dock.

Minutes from St Michaels, this peaceful retreat will have guests never wanting to leave. Panoramic views of the bay greet our guests upon arrival. In the mornings toss the crab pot from the dock & steam crabs by lunch. An afternoon bike ride will not disappoint. Evenings can be spent enjoying one of the local restaurants or catching the sunset from the homes wonderful deck. Talbot County Licensure: STN-24-14

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What guests are saying

Ferry Bridge House

5 out of 5 average rating, 8 reviews4 months ago

Beautiful property - everything was just as advertised and more. Spacious bedrooms with comfortable beds. Quiet, private location with gorgeous views. The hosts were exceptional - very gracious, thoughtful and accommodating to any possible need. We were delighted to find the house so beautifully decorated for Christmas. It made for a very special stay. Thank you!

Home in Easton

What guests are saying

Tuckaway Cove Relaxing waterfront property

5 out of 5 average rating, 49 reviews8 months ago

I have only praise for Annette. However I am unhappy with this app’s policy of not allowing me to use a gift card for the final payment. They automatically charged me without notifying me when payment was due. Once done unable to reverse or credit account. Knowing that the gift card has an expiration date it now makes our once a year usage difficult.

Home in Easton

What guests are saying

Beautiful Waterfront Getaway on the Choptank River

5 out of 5 average rating, 16 reviews8 months ago

Book your stay! This was probably one of the nicest AirBnBs we have stayed in and we have stayed all over the world. Lee's property is absolutely a hidden gem! The space was perfect for our family of 3. We cooked all of our meals in (went to a local seafood market to fish and scallops) and we brought other food with us to grill. We fell in love with sitting on the porch looking out at the water and loved sitting on the beach all day long. Lee greeted us on our first night there and he checked in throughout our stay. We met his son as well and our daughter loved playing with Copper the dog. We enjoyed all of the amenities (paddling boarding, kayaking, paddle boating, fishing, beach, and fire pit). We kept finding ourselves talking about coming back next summer with friends! Everything was exceptionally clean and beautifully decorated. We enjoyed the peacefulness of the property and watching the wildlife come and go. Cannot wait to go back!

Place to stay in East New Market

What guests are saying

Crow’s Nest Cottage - Down Under: Chesapeake Bay

4.94 out of 5 average rating, 17 reviews1 month ago

I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

Apartment in Annapolis

What guests are saying

Cheerful Cottage Home in Beach Community

4.97 out of 5 average rating, 32 reviews5 months ago

Heather was a wonderful host and was so proactive with making sure we knew exactly how to find her rental and get in the house with no issues. We have stayed at quite a few properties in Annapolis and this is the one we will look for availability first during our future stays.

Home in Annapolis

What guests are saying

Cottage at Goose Neck Point

5 out of 5 average rating, 12 reviews7 months ago

A beautiful spot in a perfectly peaceful place. The Cottage was lovely with every convenience and comfort thoughtfully arranged. EXCELLENT treats and a truly welcoming feeling. Views of the water abound. Bed is VERY soft and all linens first rate! Highly recommend it as a place to rest, relax, and recharge!

Guesthouse in Royal Oak

What guests are saying

Panoramic water views

5 out of 5 average rating, 15 reviews1 week ago

My wife, baby daughter and myself came here for our spring break. The views from apartment were spectacular and we enjoyed watching the boats coming and going. Maria was a gracious host and gave us lots of fantastic local recommendations. The apartment was clean and comfortable and the kitchen was well stocked for us to use. We loved our stay here, and will try and come back on the future.

Home in Tilghman Island

What guests are saying

Two Oysters House 2025 Remodel

4.74 out of 5 average rating, 80 reviews6 months ago

The house is in a beautiful location and has a beautiful view. The house had plenty of areas to sit and chat/relax inside and out! We were too late in the season for the pool, but that is a wonderful ammenity to have. I would highly recommend this home and would stay there again. It would be a little hard to find at night, but the directions are good!

Home in Saint Michaels