Lloguers vacacionals a Still Pond

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.

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 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

Country Living 3 Bed Historic Cottage Apartment

The Elliott House was built in 1854 and served as a general store and in later years a sporting goods & hardware shop. The owners have restored the residence, keeping many original characteristics but making comfortable for 21st century guests with wi-fi, central heat/AC, smart TV’s, & more! Spacious private backyard enclosed by bamboo and foliage. Tastefully appointed with outdoor Amish crafted furnishings. Only 1.5 miles to Betterton Beach and 10 minute drive to historic Chestertown.

Vintage Waterfront Cottage with Stunning Sunsets

This unique Red Point Cottage offers vintage charm, rustic accents and incredible sunsets overlooking the Chesapeake bay from a 50 ft cliffside waterfront location. Our cottage has two bedrooms, one queen and one king - all bedding is provided and included. We have an open cottage concept with water views from every room. A stone gas fireplace, fully equipped custom kitchen, central air, washer & dryer, WIFI, flat screen TV, stereo, gas grill, fire pit, outside shower and front porch.

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!

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.

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.

Bright, new apartment in the heart of Chestertown

Flooded with light and in the center of all Chestertown has to offer. Have a front seat to Chestertown’s festivals. The apartment spans the entire front of the second floor of the recently restored building, built in 1877. Open living room/dining area/kitchen. Historic character with all modem conveniences, including dishwasher, washer/dryer, Smart TV and high speed wifi internet access. Off-street parking for one car on first come first served basis with ample street parking.

Turtle Cove Room at Still Pond Inn

Welcome to the Turtle Cove Room at Still Pond Inn, a bright coastal guest room featuring a queen bed with a pillow-top mattress, layered textures, and coastal accents that make the space feel fresh and inviting. Guests can enjoy a private en suite bathroom with a tiled walk-in shower, glass doors, built-in shelves, soft towels, and fresh bath essentials. The room also includes cozy lighting, and a quiet sitting area for morning coffee, reading, or unwinding after a day out.

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.