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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 where you can catch your own fish or crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars and admire the wildlife. 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

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Cozy 3-bedroom home w/ screened in porch & 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.

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Totally Renovated historic house near town center

Renovated 19th century home with modern conveniences. 55” TV in family room, 2 more. 1st floor bedroom with full bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from Wash College and the C'town waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 more bedrooms with queens. 1 loft connected to a 2nd story bedroom with 2 twins. Fenced yard and an acre of private gardens. Fire pit. New Weber grill

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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!

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Harbor View Haven | Waterfront w/ HOT TUB + Dock!

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 - Kayaks + Bikes - Boat Dock - Ping-Pong Table - Outdoor Dining

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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!

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NEW Chestertown Retreat

Enjoy this new semi-detached home (construction completed in July 2023) with new furnishings, fully stocked with everything you need and private fenced back yard. Located less than 1/2 mile to Washington College and 1.5 miles to downtown, this home is close to everything Chestertown has to offer. Perfect for parents and families visiting students, hunting trips, weddings or anyone looking to enjoy the many eastern shore/Chestertown events and attractions.

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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.

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Down by the River

Relax while taking in the beautiful river views in this bright and welcoming home. Walk to town to enjoy all the delights of charming historic Chestertown. Kayak on the river, unwind on the dock, cook a gourmet meal in the huge open kitchen, relax by the fire-pit. This fully updated, light, and open home is a calming oasis and welcoming gathering place for family and friends. Fully accessible as well.

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Waterfront house with private dock & kayaks!

Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy sunset views from the private dock, watch wildlife, and explore the creek with kayaks. Modern amenities like central AC, WiFi, and a gas grill ensure a comfortable stay. With 2 bedrooms and water views from nearly every room, it's the perfect retreat for relaxation and exploration.

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Simple Living on the Pond

Cross over the Chesapeake Bay Bridge from the west and life immediately feels relaxed. Come stay at a simple and comfortable house with just enough amenities. Located in a wooded area on a gravel road next to a pond and close to Chestertown (5 min. drive) and Rock Hall (25 min. drive). Unwind on the screened back porch to listen to the birds, see a heron, or watch turtles sunning in the pond.

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Pirates Perch

Rock Hall's most convenient vacation rental. Right on the parade route and walking distance to shops, ice cream, coffee, groceries and more! Sleeps 8 with 2 full baths. The master bedroom with full bath is on the 1st floor. Kitchen, dining room and living room. 3 TVs with WiFi internet. Off street parking for 3 full size vehicles.

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Chestertown Watson Family Farm

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Creek Cottage at Reed Creek | an ESVR property

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Rockfish Keeper

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The Mariner's House

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Holly Point on the Water

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Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

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Private Peaceful Waterfront House w/ Pool, Hot Tub

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The Peaceful Getaway (with private pool & hot tub)

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The Bay House - just a few steps to the bay!

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Quiet, Shabby-chic home in downtown Chestertown

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Spacious Victorian close to everything in RH!

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Mac's Waterfront Wonder

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Gable’s Landing on the River.

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In Town Chestertown Rancher (1 Block to College)

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KozyKentIsland Home w/screened porch*Weddings*USNA

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Nautical Nook

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Historic Chestertown

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Entire River Front Home - 4 Bedrooms 4.5 Baths

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The Patriot House-Chestertown, MD

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Waterfront w/Pier &Walking Distance to Chestertown

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Heron Creek

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Peaceful Acres Guest House (A Nature's Getaway)

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Goose Haven, new waterfront house on Fairlee Creek

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Farm House w/ Water Access (near Chestertown)

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