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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 6 hours a day) & 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, fire pit

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

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets Parties & 14 max guests. Book Today!

The Perfect Waterfront Escape!

*NEW In-ground Large private pool! A private oasis. This exceptional 5 bedroom, 6 bathroom Rural waterfront Eastern Shore home sits on over 7 acres and boast endless water activities, including kayaking, crabbing or fishing. You can drift off to sleep in the oversized main suite with a perfect waterfront view! Enjoy the Eastern Shore lifestyle in this beautiful backyard complete with a mesmerizing water garden and firepit. Crab or fish from the shoreline for dinner or take in an amazing sunset!

⫷ Massey on the Lake

Remodeled (2015) Wye Mills HISTORIC house, Built in 1880. Privately located on 1 acre on Wye Lake, private lake access for fishing, sand bar, KAYAK provided! There is a GAS GRILL and a picnic table for your enjoyment, as well. This Property in the past was a working farm, still remains of older farm building are located on this property. Please look thru all the pictures provided to give you a clear vision of the property. If you enjoy wild life, Rustic life style , this will be your paradise.

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.

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!

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!

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!