Semesterboenden med uteplats i Chestertown

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.

3 bedroom home with pool and game room

Forget your worries in this spacious and serene space. 5 miles outside of the town of Centreville. 15 miles to Chestertown. Custom built home sits on 4 acres in the middle of a 200 acre farm. First floor master bedroom and master bath. Living room, half bath, kitchen and dining area. Large back porch facing pool. Second story has full bathroom and two bedrooms. Each bedroom has an extra room inside. Also upstairs is a game room with a pool table. 1-king bed 1-full bed 1- queen bed 1- twin

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.

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!

Pole Pole House - Downtown Chestertown Retreat

Welcome to your perfect getaway in the heart of downtown Chestertown! This beautifully renovated duplex blends historic charm with modern comfort, offering a warm and inviting space just steps from the town's best restaurants, shops and waterfront views. Inspired by 5 years spent on the Swahili Coast, Pole Pole (Pol-eh Pol-eh) means "slowly slowly' - a philosophy of intentional living and resilience. We invite you to slow down, reflect, and enjoy the quiet luxury of unhurried time!

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

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.

Historic Downtown Garden Oasis with Private Patio

Welcome to 108Annex — a one-bedroom guesthouse tucked into the courtyard of a historic 1890s home in Chestertown, Maryland. Whether you're here for a long weekend on the Eastern Shore, a quiet escape from the city, or one of Chestertown's celebrated events, this is the kind of place you'll want to come back to. Steps from the Chester River, High Street restaurants, and Washington College, with a private patio and beautiful garden setting to return to at the end of the day.

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Safe, quiet neighborhood close to downtown!

Private, clean, spacious studio apartment in a safe, quiet community located on the Chesapeake Bay. Walk out the yard to a walking/bike path leading you to the North Point State Park. Bikes available upon request. *6-14 miles from most major hospitals and great for traveling professionals. *9 miles from Camden yards and M&T Bank to attend sports events. *12 miles from BWI airport. Will decorate for special occasions Free, convenient parking Hot tub

2 Beds, 2.5 Baths - Perfect Downtown Location

Charming and inviting, this beautifully updated home in historic Chestertown offers the perfect blend of comfort and location. Featuring 2 bedrooms—each with its own en suite bath—plus an additional half bath on the first floor, it comfortably accommodates up to 4 adults. Enjoy bright, thoughtfully designed living spaces throughout. Just a few blocks from downtown shops, restaurants, and waterfront, and an easy walk to Washington College.