Holiday rentals with a kayak in Kent County

4.95 out of 5 average rating, 141 reviews

Farm stay in Chestertown

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

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

5 out of 5 average rating, 40 reviews

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

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, 19 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, 26 reviews

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

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

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.

4.97 out of 5 average rating, 90 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!

Superhost

Home in Queen Anne's County

5 out of 5 average rating, 3 reviews

River Heights Retreat (pool and hot tub)

Welcome to this secluded waterfront oasis with a heated salt water pool, hot tub and kayaks! Come and make memories with your family and friends! HIGHLIGHTS POOL HOT TUB BREEO FIREPIT ESPRESSO MACHINE This newly renovated cottage with a pool is located on the banks of a river and has lovely water views from the spacious kitchen and living room, and has a luxurious master suite with a king bed and a bathroom with a double vanity and a luxury tile shower.

4.93 out of 5 average rating, 30 reviews

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!

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Kent County kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday 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.

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.

4.96 out of 5 average rating, 55 reviews

Home in Rock Hall

Eastern Neck Water Paradise w/Brick oven & Beach

JuanitaRating, 5 stars2 weeks ago

Our stay at this place was so amazing! It had something for everyone to do! I feel it was very kid-friendly with lots of sand toys, a kiddie pool and inside toy too. The kitchen was well- stocked! We used the brick oven one night and boiled crabs. Martha responded quickly to our questions. She made it very easy for us to get into the house. We most definitely would come back again!

4.95 out of 5 average rating, 41 reviews

Home in Middle River

Waterfront Home with Private Beach, Stunning Views

AbbyRating, 5 stars2 weeks 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

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! ❤️

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.

5 out of 5 average rating, 49 reviews

Goose Haven, new waterfront house on Fairlee Creek

CindyRating, 5 stars1 day ago

This home was comfortable for 4 couples to share for a weekend and be able to visit with our other friends that live across the creek. The kitchen was well stocked with everything including some tin foil and plastic wrap - a plus to keep our leftovers. The house has kayaks, bikes and more to feel like home. A great spot on the eastern MD shore!!