Vacation rentals with a kayak in Queen Anne's County

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Top-rated kayak rentals in Queen Anne's County

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Guest favorite

Home in Grasonville

4.94 out of 5 average rating, 225 reviews

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Nov 3 – 10

$415 per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 22 reviews

Away at the Bay: New Home on the Chesapeake Bay!

Welcome to Away at the Bay! A new build, 4 bedroom house right on the Chesapeake Bay. Very family friendly, and in walking distance to a small community beach. Enjoy kayaking, biking, and crabbing on Kent Island right out of your front door. Perfect for multiple families (especially with younger kids), or working from home with a view! 15 minutes off the Bay Bridge and easy access to groceries stores, outlet shopping, and a brand new Target. Come stay with us and enjoy being "away at the bay"!

Apr 10 – 17

$675 per night

Guest favorite

Guesthouse in Chester

5.0 out of 5 average rating, 40 reviews

Waterfront Guest Cottage: Sunsets, Pool, Pier

Enjoy this coastal guest cottage on waterfront property with stunning sunsets and views of Cox Creek. Its the perfect spot both winter or summer for a romantic weekend-getaway, friends weekend, mother/daughter weekend. or family vacation. Enjoy quiet mornings on the balcony with coffee. In summer, Spend time outside swimming in our newly renovated pool, or drinking wine at the local winery. In winter, curl up by the cozy fireplace inside or outside by the firepit. No children 12 and under.

Feb 10 – 17

$599 per night

Guest favorite

Home in Centreville

4.86 out of 5 average rating, 14 reviews

Historic Centreville Home

Historic and very charming home! Built in 1881 with modern touches. 1200 sq feet home. Fully fenced-in, spacious backyard. Very open kitchen/living room area with passthrough to view TV from kitchen. Tree house with electricity! Approximately 300 yard walk from the Wharf (public landing). Kayaks available for your own use! 80 yard walk to the most popular restaurant in town, Doc's. Walking distance to downtown Centreville and Millstream Park trail. Main bedroom boasts unique barn doors.

Jul 25 – Aug 1

$159 per night

Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 68 reviews

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Jan 9 – 16

$141 per night

Guest favorite

Barn in Queenstown

5.0 out of 5 average rating, 41 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.

Oct 21 – 28

$540 per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 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.

Sep 13 – 20

$121 per night

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 31 reviews

Harbor View Haven | Waterfront w/ HOT TUB + Dock!

BNB Breeze Presents Harbor View Haven! This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: ★ HOT TUB! ★ 2 Outdoor Gas Fireplaces ★ Jura Espresso Machine ★ Kayaks + Bikes ★ Boat Dock ★ Ping-Pong Table ★ Outdoor Dining

Dec 5 – 12

$429 per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 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.

Jun 4 – 11

$489 per night

Guest favorite

Apartment in Chester

4.97 out of 5 average rating, 234 reviews

Cozy Waterfront Apartment Chester, MD

*We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to sit & enjoy beautiful water views!

Feb 15 – 22

$110 per night

Guest favorite

Home in Sparrows Point

5.0 out of 5 average rating, 52 reviews

Pristine Waterfront Home with Bay Views for Miles

Welcome to our home on the Chesapeake Bay! This freshly renovated 3 BR, 2 1/2 BA home sits directly at the water's edge, nestled toward the end of a quiet street. This house is 20 minutes east of Baltimore, yet you’ll feel like you’ve entered a different world. Take in the many sights and sounds of the bay from our huge wraparound deck or explore the bay by kayak. Inside, you’ll love the comfortable yet stylish living spaces, serene bedrooms, and luxurious baths.

May 9 – 14

$495 per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

Nov 15 – 22

$450 per night