Holiday rentals with a kayak in Cecil County

Breathtaking Waterfront Now booking Fall 2025

Booking Fall 2025/ Summer 2026 The incredible 4-bed 2-bath water-facing home is the ultimate getaway. Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with a $125 docking fee), jet ski and fishing gear. Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2), or simply relax on the peaceful deck that spans the back of the home. May-September is when the private saltwater pool and jacuzzi are open. Closed Oct- mid May

Waldins Chesapeake

Winter sunrises or summer water fun, Waldins is a beautiful retreat any time of year. With the million dollar view just out back there is no need to go anywhere else. Recently renovated the house is immaculate. State of the art entertainment system and modern kitchen provide all the accouterments necessary for a comfortable stay. On the water without the typical "beach house" decor, this place is one of a kind . Bring your water toys, dock at our 160' pier and maximize all the area has to offer

Comfortable and quiet 3-bedroom

This charming 3-bedroom, 2-bathroom home in historic Havre de Grace is the perfect mix of perfect location and relaxing getaway. Easily stroll to shopping, restaurants and nightlife in downtown Havre de Grace, or take a kayak down to the Susquehanna River. Three private bedrooms feature a king bed, queen bed, and twin bed. One bathroom has a tub-shower combo and the other has a stand-up shower. Kitchen has all major appliances and gadgets. Parking is free and plentiful. It doesn't get better!

Large Cabin w/ RiverView&Hot Tub

Escape to our spacious cabin with river view! Only 2-3 hours from NYC/DC. Secluded in nature, it's a perfect, peaceful getaway for couples & small families. Enjoy stunning views, tranquility, and nearby amenities such as restaurants, vineyards, horse riding, kayaking, and more. Soak in the hot tub under a canopy of stars, enjoy a peaceful evening around the fire pit, or play pool/air hockey/ping pong or board games in the game room. Relax and create lasting memories. Book your stay today!

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

The Sunset House

Spacious 5-bedroom, 3-bathroom home in Charlestown, MD, perfect for families and groups! Enjoy 2 king beds, 3 queen beds, a fully stocked kitchen, and a cozy outdoor entertaining area with a grill, fire pit (wood provided), and a relaxing hot tub. Just 1.5 blocks from the Chesapeake Bay, with kayaks and paddleboards available for your adventures. Plenty of games included for added fun. Ideal for your next getaway! Bringing a boat? Utilize the mooring while you stay!

Catching Sunsets on the Bay

Come and enjoy this brand new home, built for making memories on the Chesapeake Bay! Our spacious 3 bedroom, 2.5 bath is perfect for your next getaway. Our cozy, yet modern home is within feet of the Northeast River where you can take in the beautiful views, go kayaking, swimming or boating, or take a 12 minute drive to the new Great Wolf Lodge! Our home is perfect for couples or families as we have games, toys, and a pack n play if needed!

Cozy 4 BR 3 BA Near Chesapeake City

Peaceful, cozy modern cottage with many amenities in a water-oriented community along the Bohemia River. Just minutes from Chesapeake City and located across the street from the water. Our house is perfect for family vacations, tranquil retreats, girl/guy getaways, weddings, wedding guests. Two queen master BR’s w/private baths on the first floor, second floor has one larger BR w/twins and smaller BR w/daybed +trundle and shared bathroom.

Chesapeake Waterfront Vacation Rental with Dock

Relax at this peaceful waterfront vacation rental on the upper Chesapeake. 2 King beds, a Queen, a large Bunk bed, and a Day bed: 5 BRs, 2 Bath with spacious deck. 100 foot dock (has water and electric) with lots of room for water activities and fun in the sun. Tie off your boat or jet skis. 2 kayaks provided. Very clean and comfy. Linens and Kitchen amenities provided. All four 2nd floor bedrooms have smart TVs as does the living room.