Holiday houses in Still Pond

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.

Charming Haven on High

Featuring an open, updated kitchen, 2 bedrooms, 1.5 bathrooms for up to 4 guests. Explore historic downtown with unique shops, delightful dining options, & the Arts & Entertainment district that stretches to the Chester River, just a 5-min. walk. Numerous events, include the Tea Party Festival, Summer Concert Series, First Fridays, Downrigging Weekend, the Annual Dickens of a Christmas & Saturday morning Farmers Market. Steps from Washington College, it’s ideal for parents & alum visiting.

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.

Heart of Historic Chestertown - Church Alley

This beautifully restored townhouse blends colonial charm with modern comforts, plus the added convenience of its unbeatable location. On a quiet block in the heart of historic downtown, all the local staples are just steps from your door-- the farmers market, beloved festivals, fine dining and the scenic Chester River! Enjoy cooking in the fully outfitted kitchen, dining al fresco on the patio, and entertaining your company with two stylish and distinct living spaces on the first floor.

Chesapeake Getaway | Marinas | Woodland Views

Escape to our peaceful retreat on Maryland's Eastern Shore, nestled in a quiet, wooded neighborhood near historic Chestertown. The Chesapeake Bay is known for its wildlife and serene landscapes. This cozy haven is perfect for unwinding and reconnecting with nature. After exploring Chestertown's charming streets, local shops, and delightful restaurants, or kayaking at nearby Worton Creek, relax in our comfortable home, where you can read, play games, or enjoy the peaceful surroundings.

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Sweet Bay Overlook

Take it easy at this unique home overlooking the Chesapeake Bay. You will enjoy watching the amazing sunsets on the bluff as the eagles, ospreys and boats drift by. Our little house was built in the 1960’s by a brick mason who was very good at his trade. In recent years, the home had fallen into disrepair, but a talented Amish craftsman purchased the house and renovated it from top to bottom. The Sweet Bay that you see today reflects his incredible attention to detail and quality.

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.

Long Beach Cottage, Hot Tub, Beachfront

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Beachcomber Suite at Still Pond Inn

Step into serenity at The Still Pond Inn’s Beachcomber Suite, a 456 sq ft ground-floor retreat blending historic farmhouse charm with modern comfort. Enjoy a private entry, bright living area with queen pullout sofa, a queen bedroom with fireplace, kitchenette, and spa-like bath. Shared perks include a screened porch, lawn, grill, and endless coffee. Close to Chestertown, Rock Hall, beaches, and marinas—ideal for couples, solo travelers, or small families.

Farm House w/ Water Access (near Chestertown)

The perfect setting for family and friends (up to eight people) to gather and get away to relax. Situated on 140 acres adjacent to Still Pond Creek in Worton, there's room for everyone to spread out -- enjoy the fresh air, outdoor activities and relax in solitude watching abundant wildlife (birds, deer, rabbits, groundhogs, and more!). Chestertown is just 8 miles away with a year round farmer's market, local shopping, art galleries and more.