3 Br Private Vacation Home Vacation Rental In Chester, Maryland
Discover the beauty of Kent Island from this 3-bedroom house. Built in 2024, this fantastic property offers a king bed, a queen bed, and two twin beds for a peaceful night's sleep. The family room...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Chester, Maryland
Summary:Sink into the hot tub and watch the sun set over the Chesapeake Bay. This waterfront home in Chester has everything you need to unplug a 270-degree sunroom with stunning water views, a fire...
Created Jul 20, 2026
1 Br Private Vacation Home Vacation Rental In Chester, Maryland
Enjoy easy access to everything from this perfectly located room with water views off of Rt. 50 between the Chesapeake Bay and Kent Narrows. Guests have their own private entrance to an oversized...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chester, Maryland
BNB Breeze Presents: Crab AlleyWelcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Chester, Maryland. This beautiful property offers a perfect blend of relaxation...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chester, Maryland
Charming Kent Island Retreat 4 BR 2.5 BA Pool Table Near the Water Brand New ConstructionEscape to the Eastern Shore with this spacious and comfortable 4bedroom, 2.5bath havenperfect for family...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chester, Maryland
We pride ourselves on keeping our family vacation home very neat and clean. We will meet you to check you in, give you a brief tour (ie. show you kayaks, life jackets, thermostats, etc), and make...
Created Jul 20, 2026
1 Br Apartment Vacation Rental In Chester, Maryland
*Only accepting bookings from travel healthcare workers* *We live on the property* NO SMOKING OF ANY KIND is permitted in this apartment or on the property whatsoever. The apartment air ducts are...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chester, Maryland
Beautiful waterfront property on 10 acres of land within a short drive to Annapolis and local Kent Island restaurants. Beautifully decorated home with amazing view of the water and access to the...
Created Oct 12, 2025
3 Br Private Vacation Home Vacation Rental In Chester, Maryland
Enjoy waterfront views of Cox Creek from this stunning custom home on Marylands Eastern Shore. With its private pier, expansive outdoor spaces, and well-appointed interiors, this property is...
Created Oct 12, 2025
5 Br Private Vacation Home Vacation Rental In Chester, Maryland
Wade a Minute ChesterEscape to a charming waterfront retreat located in Chester, MD, this impressive 5-bedroom, 3.5 bath vacation home offers the perfect blend of small town tranquility and...
Created Jul 20, 2025
4 Br Private Vacation Home Vacation Rental In Chester, Maryland
Pier Pleasure Retreat: Your Waterfront OasisWelcome to Pier Pleasure Retreat, a newly renovated 4-bedroom, 4-bathroom waterfront home that blends luxury with relaxation. Perfectly situated along...
Created Jun 15, 2025
3 Br Private Vacation Home Vacation Rental In Chester, Maryland
Cozy yet modern rancher equipped with 3 bedrooms, 2 baths, and spacious open floor plan! Whether youre looking to be close to your family, attend a wedding, explore the Chesapeake Bay and its...
Created Jun 8, 2025
4 Br Private Vacation Home Vacation Rental In Chester, Maryland
Weekend or weekly getaway in this 3000 SF house located in Kent Island MD, surrounded by the beautiful waters of the Chesapeake Bay. The closest outlet at 30 minutes away. Closest beaches and...
Created Jun 8, 2025
