Vacation rentals with a kayak in Kent County

A view of a paddleboarder gliding on calm water, with a spacious home featuring large windows in the background. Lush trees provide shade, and several outdoor seating areas are visible on the green lawn. Children can be seen playing near the water's edge.

4.93 out of 5 average rating, 45 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

4.96 out of 5 average rating, 55 reviews

A spacious dining area is shown with large windows exposing views of the tranquil water. A long wooden table is surrounded by eight chairs, while light wooden paneling complements the natural scenery. The sliding glass doors provide access to an outdoor deck.

Home in Rock Hall

Eastern Neck Water Paradise w/Brick oven & Beach

This beautiful breathtaking waterfront home is the perfect place for your vacation. This spacious 3 story house sits along the back waters of the Chesapeake Bay, along Grey’s Inn Creek with it’s own private pier and beach area!! Kayaks and paddle boards available for guests to use! The water is 6’-9’ deep depending on the tide. You can bring your own boat or if you’re interested in renting one, Lankford Bay Marina is only 15 minutes by car or boat, must have a MD boaters safety card to rent

5 out of 5 average rating, 39 reviews

A modern, two-story home is surrounded by trees, featuring large windows that allow natural light to fill the interior. A wooden deck extends from the main level, providing access to an outdoor space. The house is elevated, supported by stilts, enhancing the scenic views.

Home in Rock Hall

Water Views in Rock Hall

Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full baths. Enjoy the screened in porch, sunning yourself on the deck or warming up by the wood stove in the wintertime. Fun tile work in the bathrooms, a giant soaker tub, built in bunk beds (full size), rugs imported from Morocco & lots of original art, brings this home to life! This house is playful & has lots of personality. Walk or bike to all the marinas & eateries in town!

Guest suite in Chestertown

A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.

4.99 out of 5 average rating, 225 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

5 out of 5 average rating, 18 reviews

Holiday Escape to the Riverside

Relax with the whole family or big group at our peaceful river home. Huge waterfront property. Bedroom, dining and living room river views. River and tidal beach access. Kayak, SUP or canoe. Enjoy backyard games, outdoor dining, hammock or fire pit. Massive waterfront screened-in porch with 2 dining and 2 seating areas. 10 min walk to adorable historic downtown. Festivals, art galleries, bakeries, ice cream, shops, spa & playground. This is our happy place - we hope it becomes yours!

4.95 out of 5 average rating, 73 reviews

Waterfront w/ Hot Tub + Dock | Harbor View Haven

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 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

5 out of 5 average rating, 25 reviews

Two green kayaks are securely stored on a wooden rack beside the river. Sunlight highlights their vibrant colors against the backdrop of gentle water and greenery. The serene environment invites water activities and relaxation by the riverside.

Home in Millington

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

5 out of 5 average rating, 110 reviews

A well-maintained grassy area leads to the water's edge, framed by lush greenery. Two kayaks are positioned on the shore, ready for use. The calm river reflects the clear blue sky, creating a serene atmosphere.

Apartment in Chestertown

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!

4.94 out of 5 average rating, 93 reviews

A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.

Cabin in Worton

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

A cozy outdoor seating area is set up on a grassy lawn, facing the water. Adirondack chairs and a low sofa surround a fire pit, creating a welcoming space for relaxation. A private dock extends into the Chester River, offering scenic views of the water.

4.97 out of 5 average rating, 89 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!

4.93 out of 5 average rating, 30 reviews

An expansive deck with a wooden dining table is surrounded by several chairs. Lush greenery provides a natural backdrop, and a winding path leads down toward the waterfront, offering a view of the serene Chester River.

Home in Millington

Lark's Nest on the Chester River

Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the views and dine alfresco on the oversized deck. Centrally located just 20 minutes from all of the events, eateries, shops and galleries in Historic Chestertown. Perfect, family and pet-friendly home for Washington College students, parents and alumni. Book today for your family reunion, wedding parties, or romantic get-away!

4.94 out of 5 average rating, 158 reviews

The chalet is depicted at night, showcasing its A-frame structure with large illuminated windows. The wrap-around deck features outdoor seating, while the surrounding trees provide a sense of seclusion. Soft lighting from inside highlights the inviting interior layout.

Farm stay in Chestertown

Blue Heron Farm Waterfront Chalet

Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.

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Popular amenities for Kent County kayak rentals

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Air conditioning

House rentals with a kayak

5 out of 5 average rating, 18 reviews

The Lazy River

MichaelRating, 5 stars5 months ago

This was our third stay here. The house is quite spacious and very nice. Beautiful views of the river. Three large bedrooms with lots of space. The large kitchen easily allows cooking for a group. We’ve only stayed in the winter — in the summer, the large deck, grill and river activities would be wonderful.

A spacious two-story home is surrounded by lush green lawn and mature trees. A stone path leads to its welcoming entrance. Large windows reflect sunlight, offering views of the nearby water. The serene setting is enhanced by the gentle presence of the surrounding nature.

4.99 out of 5 average rating, 107 reviews

Entire River Front Home - 4 Bedrooms 4.5 Baths

JeanneRating, 5 stars13 months ago

We had a wonderful stay at this beautiful place. Our extended family and dogs thoroughly enjoyed the private and peaceful location. Bobs place was provisioned very well. We appreciated the numerous coffee cups, wine glasses, etc. it felt very much like staying with family. Lovely art throughout too.

4.95 out of 5 average rating, 41 reviews

A serene waterfront view is captured, showcasing calm waters reflecting the cloudy sky. A seating area with six chairs is positioned near a fire pit on a patio, with a swing nearby. The beach is lined with trees, creating a natural border.

Home in Middle River

Waterfront Home with Private Beach, Stunning Views

AbbyRating, 5 stars1 week ago

We rented this place for my parents 50th anniversary. The place was amazing and fit 5 families comfortably. The house had everything you could have imagined that you needed and then more. The place was off the beaten path and exactly what we were looking for. It was peaceful and quiet. The amenities including life preservers, kayaks, and paddle boards was awesome. We enjoyed a fire every night. I highly recommend this place!

4.89 out of 5 average rating, 53 reviews

A saltwater pool is surrounded by a landscaped area featuring trees and shrubs. A view of the waterfront can be seen in the background, with natural grasslands and tall reeds composing the serene setting. Outdoor seating is available nearby.

Home in Church Hill

Private Peaceful Waterfront House w/ Pool, Hot Tub

LenaRating, 5 stars11 months ago

This was our 2nd year at Peaceful Waters. It is indeed just that! Peaceful! Perfect and beautiful location. Everything needed is there to assure a wonderful carefree stay. The place is well stocked, clean and is just as it reads and appears! My group of 16 loved the place AGAIN this year. Hopefully, planning to go back next year. Matthew and Rose are great to work with! ❤️

The image captures a serene waterfront view featuring a dock extending into calm waters. A grassy area borders the water, with several boat slips visible. A fire pit stands in the foreground, framed by distant trees and clear blue skies.

4.69 out of 5 average rating, 32 reviews

Waterfront 3bed/2.5 bath w/dock&beach close 2 town

AndrewRating, 5 stars3 weeks ago

Friendly neighbors and very enjoyable stay. We felt like we were part of the neighborhood. Dock with active Osprey nest 150 feet away was fantastic. Many birds. Would definitely stay there again. Also stocked with snacks, coffee and a bottle of wine are big pluses too.

A wooden dock extends into a calm river, featuring three red Adirondack chairs at the end. Surrounded by trees, the still water reflects the overcast sky, providing a serene outdoor space for relaxation.

5 out of 5 average rating, 47 reviews

Goose Haven, new waterfront house on Fairlee Creek

NikhilRating, 5 stars2 weeks ago

The place was really nice, and the bonfire in the woods made it even better. It would be perfect with a warm light installed near the bonfire area — it gets a bit too dark without it.

4.93 out of 5 average rating, 15 reviews

A front porch offers a view of the expansive Chesapeake Bay. Two red cushioned chairs are positioned around a small round table. Lush greenery and a pathway lead towards the waterfront, with the horizon visible in the distance under a clear blue sky.

Home in Betterton

Waterfront Chesapeake Bay Cottage walk to Beach

LyleRating, 5 stars7 months ago

We really enjoyed our stay at Maureen and Brian's cottage! The views and off season quiet time were wonderful. We appreciated comfy beds, a nice sitting area to look out at the water and super hot showers. Hopkins Game Farm was super close by, and we enjoyed a nice meal in Chestertown. Great hosts and we would definitely come back!