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Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Ruby's Sea Glass Cottage near Betterton Beach

This cute 1900 cottage in the center of Betterton has a full kitchen & three beautiful outdoor porches to unwind. There's one bathroom ON THE FIRST FLOOR (shower only). An outdoor shower is available seasonally! There are three bedrooms-ALL ON THE SECOND FLOOR. Enjoy the beach down the street to find sea glass or watch the sunset! SEE LISTING PHOTOS FOR INFO ABOUT THE AREA. BETTERTON DOES NOT HAVE A GROCERY STORE. Kids items upon request. Furniture/decor may be change from listing pictures.

Traveler Guest Suite @ Cinnamon By The Bay

The Traveler offers a private bedroom and fully equipped eat-in kitchen. For those guests who prefer separation from their dining area, but don’t need a separate living space, Traveler is a perfect match. Enjoy the comfort of not being awaken when someone sneaks a midnight snack, all while being easy walking distance to Rock Hall's shopping, coffee shop, restaurants, music venue, and festivities. It is one of our pet-friendly suites with easy access to the community back deck and rear yard.

Mermaid's Getaway

You will be close to everything in Rock Hall when you stay at this centrally-located ground-level apartment. Just 1 block from Main Street, park the car and walk to everything Rock Hall - shops, marinas, grocery store, ice cream shop, coffee, boat ramps, and more. A full kitchen, comfortable living room, private entrance and backyard access await you. Large grassy yard with firepit, BBQ grill, and picnic tables. Great for playing or relaxing. This one bedroom apartment sleeps 4 comfortably.

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!

Elliott House Historic Home Near Chesapeake Bay

The Elliott House is located outside of Still Pond, MD. Mere minutes to Betterton Beach (1.5 miles), Downtown Chestertown, etc A historic cottage built in 1854, this location was formerly an old time general store. In the early 1900's it was a stopping place for soldiers stationed at nearby training camps and the upstairs served as a makeshift dance hall. Current owner has kept the historic charm but added a number of modern conveniences. In the heart of Kent County with rural scenery.

Walking Distance to Marinas & Main St!

Ahoy! Embark on a wonderful vacation at “Welcome Aboard!" Our adorable home is within walking distance of waterfront marinas, restaurants, and the downtown strip, with coffee shops, stores, and more! Enjoy your morning coffee while sitting on the porch in locally purchased Adirondack chairs, then head into town to enjoy everything Rock Hall has to offer! Many of the pieces of artwork you see in our home were purchased from a photographer in town and custom framed by a nearby craftsman.

Cozy 1920's Bungalow Near Water/Local Attractions

Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.

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.

Bayside bungalow cottage by the sea

This quaint Cottage is located on a quiet residential road with quick access to the water. Located in Rock Hall, Maryland, guests will enjoy a getaway from the hustle and bustle of major cities. The Cottage boasts 1 bedroom and 1 bathroom, equipped with a private sauna. Guests are guaranteed to have a relaxing stay here at the Cottage House! Great views of Swan Creek and the Cheseapeake Bay.

River Cottage, Chestertown

Relax on the scenic Eastern Shore. We are located just off the Chester River. Step away from the hustle and bustle to our cozy cottage appointed with modern amenities. Our property is enjoyed my families and friends. Our tranquil backyard offers a fire pit and picnic table for entertaining We have bikes and kayaks for guests to enjoy while they unwind 15 mins from Washington College

Beach Haven Hideout

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps to the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.