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Private | Near BayBridge | Wedding Venue Proximity

Welcome to your Kent Island getaway! This thoughtfully decorated, private guesthouse is minutes from the Bay Bridge, offering the perfect retreat for families, couples, or friends. Skip the hotel and relax in a fully stocked home with plenty of space, a large backyard for activities, and cozy touches throughout. Whether you're here for a wedding, visiting the Naval Academy or DC, or simply exploring the Eastern Shore, you'll love the comfort, convenience, and local charm this home has to offer.

Kent Island Waterfront Cottage

Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, including spectacular sunrises and fishing off the pier (rockfish are very abundant). Perfect for families, couples, or friend groups who are looking to get away from it all. If you are traveling with small children, we have high chairs and a pack and play available upon request. Recent June 2022 updates include new memory foam mattresses, new outdoor lounge chairs, and Roku.

The Birdhouse on Swan Creek, Welcome!

An adorable carriage house with panoramic views overlooking Swan Creek -- centrally located, yet private enough to be surrounded by nature. Bird watchers would have a grand time here, with frequent Bald Eagles sightings pre-summer, ospreys, and many other waterfowls at your window in summer. Centrally located: 3 blocks from town beach, restaurants across the road and Rock Hall downtown within walkable distance, next to two local marina. Your private dock through Blue Heron Marsh to Swan Creek.

Adorable Lake Front 1BR Cottage-fully furnished!

This charming 1BR/ 1Bath cottage is located next to my primary residence. The cottage has its own private deck overlooking the Wye Mills Community Lake. The yard is spacious and pets are welcome. The yard is not closed in but safe for dogs who do not roam far. There is 1 queen size bed and queen pull out couch in the living room. Kitchen is equipped with basic appliances/ cooking and serving utensils and a full size washer and dryer. The bathroom has a stand up shower and basic necessities.

Quaint Waterfront- access, Private Shorehouse-unit

Location is everything in this comfy and affordable private unit located on the Chester River and Winchester Creek with water views. Also enjoy the hosts private water front amenities such as fishing at our private pier, boating, kayaking, paddle boarding or simply relax at the waterfront for morning coffee and sunrises or enjoy the fire pit in the evening. The community playground and beach are just steps away. Close proximity to restaurants, shopping, trails, and wedding venues.

Waterfront Guest House on 23 manicured acres

Beautiful private guest house on 23 acre waterfront estate, located on Kent Island. Perfect family getaway with private pool, kayaking, fire pit, and more. The estate is just a few minute drive to The Chesapeake Bay Beach Club/Inn, Libbey’s Coastal Kitchen, amazing waterfront restaurants in The Narrows, and Casica Vineyards & Winery. Trip to Annapolis Naval Academy- 30 min, St. Michaels - 45 min. This 1 BR Queen bed, 1 Queen Sofa-bed, 1 Full Futon, 1 Bath accommodates 4 guests.

Owl Cottage - Cozy, Private & Walkable to Town

A renovated 19th century carriage house, Owl Cottage is the perfect combination of historic ambience and modern convenience, all in the center of Chestertown. It has a 1st floor bedroom with king bed, a light-filled 2nd floor living room and kitchenette, and a third story loft, with a queen size bed. There is also a bathroom with shower on the second floor. Beds furnished with luxury linens. There is a private patio with chairs and access to over 2 acres of private gardens.

Waterfront-View of Bay from your Bed- Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Eastern Shore Charm on Winchester Creek

My place is close to restaurants and dining and great views. You’ll love my place because of the comfy bed, the coziness, and the views. My place is good for couples, solo adventurers, and business travelers; sorry no kids. Need at least three days notice to book guest house, I like to be here when you arrive, thus schedule my social activities around bookings.

Centreville Cottage

This eastern shore cottage is ideally located: a mile from downtown Centreville, 15 minutes to Kent Island, 20 minutes to Chestertown and Easton, and 30 minutes to Annapolis. The 600 square foot Cottage is completely detached from the main house and has a private, fenced-in yard (perfect for pets). Enjoy shore living at its best!

Circa 1700 Chesapeake Colonial Home

On National Historic Register. 4 bedrooms(1Q,1Full,4 twins),3 bath, study, living room, dining room, modern kitchen, farm setting, 22+acres with animals, waterfront with pier. Activities, fishing, canoeing, kayaking,bike trail. Annapolis 15min.

Carriage House

Take it easy at this unique and tranquil getaway. Walking distance to Main Street and the Chesapeake Bay with its amazing sunsets! Plenty of activities, restaurants, Eastern Neck Wildlife Refuge. a beach, boat rentals, bike riding and more!