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Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to several restaurant

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Heron Roost

Heron Roost is a centrally-located waterfront apartment on a private gated lot with a heated pool. The view from your sun deck is the best on the property with spectacular sunrise and moonrise. We are conveniently located about one mile from the Chesapeake Bay Beach Club and twenty minutes from the US Naval Academy in Annapolis. There are numerous excellent restaurants and bars nearby and the towns of Easton and St Michael’s are close. Please come and enjoy our peaceful and unique property.

Private Unit | Bay Bridge | Spacious | Families

This spacious 3-bedroom, 1-bath front unit is perfect for couples, families, or small groups seeking a convenient getaway. Just mins from the Bay Bridge and popular wedding venues, this inviting home offers modern comforts and a smart, spacious layout with its own entrance designed for privacy. Whether you're celebrating nearby or simply unwinding on the island, this charming retreat offers the perfect balance of privacy, comfort, and convenience. ⭑CONTACT US FOR DISTANCES TO WEDDING VENUES⭑

Mermaid's Getaway

You will be close to everything in Rock Hall when you stay at this centrally-located ground-level apartment. Just 1 block from Main Street, park the car and walk to everything Rock Hall - shops, marinas, grocery store, ice cream shop, coffee, boat ramps, and more. A full kitchen, comfortable living room, private entrance and backyard access await you. Large grassy yard with firepit, BBQ grill, and picnic tables. Great for playing or relaxing. This one bedroom apartment sleeps 4 comfortably.

1-br apt in downtown Chestertown (Unit 1)

Note: Beginning Oct. 4, 2023, we have eliminated all booking fees and cleaning fees. The price you see is the price you get. 1-bedroom newly-renovated apartment located in a 5-unit apartment building near downtown Chestertown, MD. Unit 1 is located two blocks from High Street (think Evergrain Bakery!) and about four blocks from the Chester River. Enjoy a shared front porch with the other long-term tenants, or use the private back porch to sit and read the newspaper or enjoy the outside.

Relax Inn

We welcome you to relax in this comfortable space for two with a plush king sized bed and a private bathroom. We love little people and have a pack and play. ☺️Enjoy the high speed internet and 50 inch smart TV. The kitchenette is equipped with a mini fridge, microwave, Keurig and a table for two. A coded entry will open into your private space that is attached to our home but separated by a locked door. We love to offer early check-in and late check-out as our calendar allows.

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.

Last-Minute Retreat Center of C’town -1 night stay

Escape to a secluded studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of private gardens. Relax in front of the fire with views of gardens in the windows. Kitchenette has large toaster oven, hot plate, microwave, fridge, and Keurig/drip coffee makers. We have an under counter filtration system for pure delicious drinking water. King bed with deluxe linens and mattress, washer dryer Same property listed on Airbnb for less with 2

Traveler Guest Suite @ Cinnamon By The Bay

The Traveler offers a private bedroom. private bath with shower, and fully equipped eat-in kitchen. For those guests who prefer separation from their dining area, but don’t need a separate living space, Traveler is a perfect match. Easy walking distance to Rock Hall's shopping, coffee shop, restaurants, music venue, and festivities. Pet-friendly for an additional fee with easy access to the community back deck and rear yard.

Harmony Haven

Take it easy at this unique and tranquil getaway. Nestled in the woods, your stay is located minutes from Sandy Point State Park, the Chesapeake Bay Bridge and downtown Annapolis. A visit to Washington D. C. or Baltimore are only 30 minutes away. Enjoy kayaking or fishing at the community beach or bring a bike and enjoy the many trails or bike routes in the area. Please note, this unit does not have a full kitchen.

Unique modern apartment with a view

Modern, stylish and airy 2 bedroom apartment overlooking Main St. in the quaint fishing village of Rock Hall on the Chesapeake Bay. 5 minute or less walk to the water, shops and really nice restaurant options. Fully outfitted w/full kitchen & overlook balcony, too! Please note that taxes, which are separate from Airbnb room charges and service fees, are due upon check-in. Those taxes are 11% lodging and state taxes.