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RetroLux Guest Suite 20 min to Downtown Baltimore

Retro-Lux Suite has the feel of a luxurious separate apartment with all the necessities you may need during your stay; from a warm and cozy bedroom, a clean and airy bathroom, to an inviting bright living room/kitchenette combo well stocked for your needs. The icing on the cake is a fantastic zen-like sunroom to enjoy your morning coffee/tea, or a glass of wine in the evening. Best of all, it's on the first floor, easy to get in and out; you can't go wrong staying at this unique guest suite.

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

Historic home near town center with NFL Sun Ticket

19th century home. NFL Sun Ticket! 55” TV in family room, 2 more. 1st floor primary with full bath. Hi speed internet. Pets welcome! In the historic district of Chestertown, 3 block walk from Wash College and the waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 bedrooms with queens. 100% cotton, 1000 thread count sheets and luxury mattresses. Loft connected to a 2nd story bedroom with queen bed. Fenced yard, acre of gardens. Fire pit. Weber grill

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.

The Patriot House-Chestertown, MD

Welcome to the Patriot House in Chestertown, Maryland. We recently renovated this beautiful home with a "Mad Men" Mid-Century modern vibe throughout. This is Two Units that combine together with connecting door for a total of 6 bedrooms and 3 remodeled bathrooms. You are renting entire first and second floors. Two kitchen and two living rooms. Wide front porch is perfect for cocktails or morning coffee. 2 blocks to Washington College and Downtown. We do not rent to undergrad students.

Hobbit House, one-of-a-kind home

Take it easy at this unique and tranquil getaway. Located within walkable distance to Cedar Lane Sports Complex (avoid the often-long line of traffic from SR136/SR543) & short drive to Aberdeen IronBirds Stadium, this private home is one of the four homes located on a gentleman's farm. This is an awesome location with close proximity to restaurants, shopping, entertainment and healthcare. Surrounded by luxury homes, you will be hard pressed to find a better neighborhood anywhere nearby.

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

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.

Classic Victorian in Chestertown

A delightful hideaway all to yourself! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Plenty of on-street parking. Professional cleaning before every visit (alcohol and/or bleach solution), combined with complete ventilation of the house 24 hours ahead of arrival.

12 M to Naval Acadmey | Waterfront

Discover the perfect blend of tranquility and convenience at our charming waterfront property. Nestled away in a serene setting yet close to all the action, this home offers an ideal escape. Imagine unwinding on the expansive screened-in porch, taking in the peaceful views of calm waters, or dropping a crab pot to catch some of Maryland's renowned Blue Crabs.

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit.

Duchess of Kent: Walk to downtown & College

Location location location! We absolutely love the proximity of our house to campus, the historic district, and the river. Chestertown is charming and there are fun little shops and restaurants around every corner. Our home is cozy and perfect for entertaining. We hope you enjoy it as much as we do!