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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

Grays Inn Creek Waterfront Pvt. Dock Kayaks & View

Recently renovated, this spacious home features 7 bedrooms and 5.5 bathrooms, comfortably sleeping 18 guests. Enjoy the beauty of waterfront living on Greys Inn Creek with a private dock offering easy boat access. Relax on the upper sundeck and take in the stunning views. Explore the Chesapeake Bay estuaries by kayak or paddleboard, or fish and crab right from your own dock. Take time to explore the quaint towns of the Eastern Shore, including Rock Hall, just 7 miles away, with its restaurants a

Chesapeake East Shore Chestertown,Pool (May1),Dock

A bright, airy, refurnished cottage set in the grounds of an 18th century farm on the eastern shore of Chesapeake Bay, shared pool (your private use 8am to 11am, 2pm to 5pm) & dock. Bring your watercraft & gear Layout is open kitchen, dining and living area. Master & bath on ground; upstairs 2 bedrm suite with bath Fiber optic & smartTVs Gas fireplace, central heat & AC Linens, kitchen utensils & Keurig coffee maker. GE washer and dryer. BBQ, deck chairs, picnic table, seating on water & dock

The Grey Goose by the Chester River

The Ole Grey Goose is a restored 1914 Victorian home. Property has a generous wrap around front porch and plenty off-street parking. Offering vintage charm with tall ceilings, hardwood floors, large formal dining room and sitting room. House is filled with antiques, oil paintings, a claw foot tub, heartland vintage stove, some stain glass windows. Stainless steel appliances. Updates include a double oven, dishwasher and built-in microwave. Free Wifi. Patio with firepit, picnic table and grill.

The Birdhouse on Swan Creek, Welcome!

An adorable carriage house with panoramic views overlooking Swan Creek -- centrally located, yet private enough to be surrounded by nature. Bird watchers would have a grand time here, with frequent Bald Eagles sightings pre-summer, ospreys, and many other waterfowls at your window in summer. Centrally located: 3 blocks from town beach, restaurants across the road and Rock Hall downtown within walkable distance, next to two local marina. Your private dock through Blue Heron Marsh to Swan Creek.

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!

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!

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!

Holly Point Guest Cottage

Take a break and unwind by getting away from it all. The one mile driveway takes you to your private cottage on the water. You’ll be looking at Churn Creek which is off of the Chesapeake Bay. It’s a great calm place to kayak. Spectacular views from inside and outside await. The open floor plan provides plenty of space and lots of windows for your viewing pleasure. Chestertown and Rock Hall are both great small towns to visit and only 15 minutes away!

Entire River Front Home - 4 Bedrooms 4.5 Baths

Quiet secluded home on the upper Chester River. All bedrooms on second floor. Master Bedroom with deck and private bath. Bedroom with double bed and private bath. Queen suite with queen bedroom and bedroom with 2 twins with private bath between. For more than 8 guests an inflatable mattress in library near half bath and full bath. Perfect getaway for total relaxation. Water access for kayaking and canoeing. Nine miles from downtown Chestertown.