Holiday rentals in Pooles Island

Sue Creek Waterfront Cottage

Kick back & relax on the water in a fully renovated private 2 story home w/ a dedicated pier located on Sue Creek on the Chesapeake Bay! Includes 2 master bedrooms each with a queen size bed and dedicated bathroom with large shower stall. Kitchen & Great room are fully equipped with all amenities for a comfortable stay. Outside includes a large patio with furniture and charcoal grill, a pier w/ 2 Kayaks & private parking area. Convenient to many water & land establishments! No Pets or smokin

Cozy Waterfront Cabin Escape

Want to escape the city for a night or week and spend time sitting by the water reflecting and taking it all in, this is the cabin for you. Two (2) bedroom, 1.5 bath shore cabin (600 sqft) that provides the perfect balance of indoor charm with outdoor access and enjoyment. Bring your kayaks and launch them from the dock and explore beautiful Seneca Creek or just sit and relax in the hot tub. High-speed internet makes this a great working location as well with raise/lower desk and 2nd monitor.

Boatyard Bungalow, 6 beds; 2 Full Baths-Waterfront

The original schoolhouse for Edgemere that was built in 1898 and converted to a residential home/marina in the 1950s. With over 2,200 sq. ft., it's a perfect environment for wedding venue preparations, family and friend reunions. Please don't exceed maximum number of twelve (12) guests at any one time in the house, during the day; or ten (10) staying the night in the house. Additional Pirate & Mermaid Bath House on property should extra toilets and showers be needed from April-November only.

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

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.

Goose Haven, new waterfront house on Fairlee Creek

Goose Haven is nestled on 2 wooded acres on freshwater, Fairlee Creek - about 1.5 hours from Baltimore, Philadelphia, and Washington D.C. It is a very secluded, brand new, 4 BR, 3 BA, waterfront house with direct water access, a dock, and plenty of room to enjoy the outdoors. There is also a public boat ramp/launch right down the road. If you don’t have a boat, don’t worry, we have a kayak & canoe for you to use. Chestertown and Rock Hall are only 20 minutes away.

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!

Bamboo Sands Beach Getaway

Where luxury meets coastal by the bay. A perfect spot to make memories, enjoy the views from the house or the hot tub.... Welcome to Bamboo Sands Villa & Captain’s Quarters, A peaceful retreat on a sandy area of the Chesapeake Bay where families can RELAX & reconnect. Here, serenity and fun flow as easily as the coastal breeze. Enjoy sandy beaches without the crowds, the sounds of waves on the bay without the oceanfront price tag, a coastal luxury getaway...

The Garden Estate: Historic Town Center Home

Step back in time without sacrificing luxury. Nestled in Chestertown’s historic district, this rebuilt 19th-century estate blends grand character with modern comfort, just 4 blocks from Washington College. Sprawling across a rare town-center acre, the sanctuary features magnificent gardens, a fenced yard, a fire pit, and a Weber grill for evenings under the stars. Inside, find a flawless layout designed for privacy, rest, and premium comfort.

Classic Victorian in Chestertown

A delightful hideaway all to yourself! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Plenty of on-street parking. Professional cleaning before every visit (alcohol and/or bleach solution), combined with complete ventilation of the house 24 hours ahead of arrival.

A place unique on sue creek

Enjoy your private apartment and deck on the water or come sit down by the waterfront and watch the Ospreys, herons, ducks and the occasional eagle. Fishing off the pier and possible small boat docking available. We are close to Rocky Point golf club, Baltimore yacht club, 20 minutes from Camden Yards and M&T stadium. We are 38 minutes from BWI. You will have private parking in a quiet safe neighborhood. Sorry, no pets allowed.

Chesapeake Bay Retreat W/Breathtaking Views

Escape to a waterfront retreat on the Chesapeake Bay with sweeping water views, vaulted ceilings, and expansive windows that fill the home with natural light. Located minutes from Rock Hall and historic Chestertown. Recently refreshed for the season with an updated layout, window tinting for comfort, and a newly added pool table. Perfect for relaxing waterfront getaways and exploring Maryland’s Eastern Shore.