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House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

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.

Cording Lodge*Pool*Pickleball/Basketball court

This beautiful property is the perfect place for your family vacation or to reconnect with friends. The outdoor living space is a dream! It has an in ground pool, beautiful patio with lots of seating area, bonfire pit and a BBQ grill, the perfect space to spend quality time together with family and friends! This 2 story, 5 bedroom house has all the amenities you need to make your weekend getaway or family vacation enjoyable. There’s boat launching at the coast guard only 1 mile from here!

Best kept secret beach-condo on the Chesapeake Bay

Beach. Pool. Sunrise and Sunset. Condo with fantastic view of calm water Betterton Beach. Beach less than 100 steps from front door, with public boat ramp, pier, & bath house. Historic Chestertown (culinary hub w/cute shops) is 15 minutes away. Thoughtfully equipped condo is a great place for families or couples to relax and unwind. Kitchen outfitted for those who like to cook. Public slips (permit required) & pier where you can fish & crab. Beach gear provided. Playground close by.

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Ruby's Sea Glass Cottage near Betterton Beach

This cute 1900 cottage is in the center of Betterton. There's a full kitchen & three beautiful outdoor porches to unwind. There's one bathroom (on the first floor) and an amazing outdoor shower available seasonally! There are three bedrooms (all on the second floor). Enjoy Betterton Beach which is down the street! Look for sea glass or watch the sunset! There is a cute park with a playground in town that the kids love! It also has pickleball, tennis and basketball courts.

Charming Home w/Great Porch

We would love to share our well-loved cottage on the Bay with you. Most loved for its beautiful views and quiet town, it is a perfect place to relax with great beach access. We think you'll love it too. Plenty of space to spread out and comfy spaces to enjoy together: whether on the screened porch (our favorite), in the updated foodie-kitchen, or swinging on the swing, snoozing in hammock or walking to the beach - you will be glad you found this place-we definitely are!

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.

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

At 3 minutes walk to the beach, this Bayfront condo perched on a bluff in beautiful Betterton is a gem the whole year through. Two level loft condo with three bedrooms (2 BR downstairs, 1 BR upstairs) as well as an ADDITIONAL sleeping loft with two single beds. Two big decks supply scenery for outdoor meals and gatherings. Come for a stay, your cares melt away. The word “peaceful” does not quite do it justice. See for yourself how calm and relaxing life can be.

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...

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.