Monthly & Winter Rentals

Escape to the serene shores of Chincoteague Island, VA and Ocean City, MD with our exclusive Monthly and Winter Rentals. Whether you're dreaming of peaceful off-season beach strolls or cozy evenings by the sea, our off season rentals are perfect for embracing the coastal lifestyle. Enjoy incredible rates and the opportunity to fully immerse yourself in the charm of our beach towns!


If you can't get enough of the ocean breeze and local culture, our extended stay options ensure you'll have all the time you'll need to savor every moment. Book now and make the most of your seaside retreat!

Address 5341 Cedar Drive, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 11700 Coastal Highway, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 11700 Coastal Highway, Ocean City
Bedrooms 2 bedrooms
Bathrooms 2 baths
Pet Friendly
Address 5216 Pine Tree Way, Chincoteague Island
Bedrooms 4 bedrooms
Bathrooms 3 baths
Pet Friendly
Address 7470 Memorial Park Drive, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 1 baths
Address 7821 East Side Road, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 6751 Megan Drive, Chincoteague
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 10900 Coastal Highway, Ocean City
Bedrooms 3 bedrooms
Bathrooms 3 baths
Address 10900 Coastal Highway, Ocean City
Bedrooms 1 bedrooms
Bathrooms 1 baths
Address 10900 Coastal Highway, Ocean City
Bedrooms 2 bedrooms
Bathrooms 2 baths
Address 10900 Coastal Highway, Ocean City
Bedrooms 1 bedrooms
Bathrooms 1 baths
Address 7282 Pointer Lane, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Pet Friendly
Address 7168 Wayne Road, Chincoteague
Bedrooms 3 bedrooms
Bathrooms 1 baths
Pet Friendly
Address 7180 Wayne Road, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 105 56th street, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 105 56th Street, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 105 56th Street, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 6163 Marsh Island Drive, Chincoteague Island
Bedrooms 2 bedrooms
Bathrooms 1 baths
Pet Friendly
Address 6201 Ocean Blvd, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 1 baths
Pet Friendly
Address 6394 Teal Lane, Chincoteague Island
Bedrooms 2 bedrooms
Bathrooms 2 baths
Address 407 Philadelphia Ave #27, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 407 Philadelphia Ave #28, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 407 Philadelphia Ave #30, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Pet Friendly
Address 3416 Willow Street, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 606 Dory Rd #202, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 11500 Coastal Highway, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 11500 Coastal Highway, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 11500 Coastal Highway, Ocean City
Bedrooms 3 bedrooms
Bathrooms 2 baths
Pet Friendly
Address 7460 Memorial Park Drive, Chincoteague
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 3488 Willow Street, Chincoteague Island
Bedrooms 2 bedrooms
Bathrooms 2 baths
Pet Friendly
Address 3134 Captains Corridor, Greenbackville
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 4411 Eastwinds, Chincoteague Island
Bedrooms 2 bedrooms
Bathrooms 2 baths
Address 3 35th Street, Ocean City
Bedrooms 2 bedrooms
Bathrooms 2 baths
Address 3 35th Street, Ocean City
Bedrooms 2 bedrooms
Bathrooms 2 baths
Address 7482 East Side Road, Chincoteague Island
Bedrooms 1 bedrooms
Bathrooms 1 baths
Address 6321 Captains Lane, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 6321 Captains Lane, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 6321 Captains Lane, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 6321 Captains Lane, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 6321 Captains Lane, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 4107 Grand Bay Court, Chincoteague Island
Bedrooms 2 bedrooms
Bathrooms 2 baths
Address 6157 Marsh Island Drive, Chincoteague Island
Bedrooms 2 bedrooms
Bathrooms 1 baths
Address 3541 Willow Street, Chincoteague Island
Bedrooms 3 bedrooms
Bathrooms 2 baths
Address 170 Captains Quarters Rd 2E, Ocean City
Bedrooms 2 bedrooms
Bathrooms 2 baths