$2,800 per month
12131 Landings Blvd, Berlin, MD 21811
Property Id: 1594126Welcome to your ideal winter retreat! Available for month-to-month rentals from October through April, this spacious home comfortably any family, offering plenty of room for everyone to enjoy their own space while spending quality time together. The open-concept kitchen and family room serve as the heart of the home, perfect for cooking, dining, and gathering on cozy
$1,950 per month
88 Tail of the Fox Dr, Berlin, MD 21811
WINTER RENTAL! Nov. 1, 2025 - April 30, 2026. This 2 bedroom 1.5 bath home is located in North Gate of Ocean Pines and is available for showings October 3rd. It comes furnished as seen. Tenants will pay for trash pick up, electric, internet and recreational fees. For showings, please contact listing office. All occupants interested must complete an online application (50.00 application fee).
Kimberly Jones Karson Keys
$5,000 per month
6620 S Point Rd, Berlin, MD 21811
Property Id: 2114734Welcome to the Assateague Holiday House, where modern luxury meets natural beauty! Overlooking Assateague Island, our new home offers the perfect retreat for family and friends. Take in stunning views from the deck or living room, with the bay as your backdrop. The home features four spacious bedrooms, three and a half baths, and comfortably sleeps up to 12. Cook with
$2,050 per month
69 Lookout Point, Berlin, MD 21811
3 bedroom 2 bath located in North Ocean Pines. This well maintained home comes fully furnished and ready to move in. It is a winter rental, November 1, 2025 - April 30, 2025. It comes furnished as seen. Tenants will pay for trash pick up, electric, internet and recreational fees. For showings, please contact listing office. All occupants interested must complete an online application (50.00
Kimberly Jones Karson Keys
$2,800 per month
241 Teal Cir, Ocean Pines, MD 21811
Property Id: 2108069 Teal Bay Circle - All-Brick Home with Canal Views & Boat DockDiscover your waterfront dream rental in the highly desirable Ocean Pines community! This exceptional home offers:Features:* 3 Bedrooms | 3 Full Baths* Fresh Paint & New Bedroom Flooring* Bright, Open Layout with Custom Finishes* Primary Suite with Private Balcony* Modern Kitchen
$1,900 per month
32 Seafarer Ln, Berlin, MD 21811
WINTER RENTAL! Nov. 1, 2025 - April 30, 2026. This 2 bedroom 1.5 bath home is located in North Gate of Ocean Pines and is available for showings October 3rd. It comes furnished as seen. Tenants will pay for trash pick up, electric, internet and recreational fees. For showings, please contact listing office. All occupants interested must complete an online application (50.00 application fee).
Kimberly Jones Karson Keys
$1,900 per month
12139 Dutch Harbor Ln, Berlin, MD 21811
Property Id: 1051015This is a beautiful house that is minutes to Assateague and ocean city! Fully furnished this winter rental won't last long since it is dog friendly.
$2,100 per month
10313 Antique Rd, Berlin, MD 21811
Property Id: 1164584Currently Occupied, Available September 2025This fully-furnished, short-term rental is a quaint 3Br/2 full bath home in Berlin, Maryland (also named America's Coolest Small Town).Perfect for traveling professionals; this cozy home is just a short drive from the beaches of Ocean City, Rehoboth, Assateague and Chincoteague Islands. You can enjoy
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