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Vacation rentals in Gwynn Island

Find and book unique accommodations on Airbnb

Popular amenities for Gwynn Island vacation rentals

Free parking on premises

Air conditioning

Homes with more space

Top guest favourite

The exterior of a two-story cottage is visible, featuring vibrant blue siding and a spacious wrap-around deck. The area is surrounded by sandy terrain and greenery, with parking available underneath the house. Tall trees and a clear sky complete the peaceful setting.

4.99 out of 5 average rating, 79 reviews

Mathews Gwynn's Island Chesapeake Bay- Sand Beach!

Top guest favourite

The cottage features a welcoming front porch with a flag gently waving. Lush greenery surrounds the entrance, complemented by a grassy lawn under a clear blue sky, creating an inviting approach to the home.

Cottage in White Stone

4.89 out of 5 average rating, 382 reviews

The Moore Cottage

Top guest favourite

A serene beach view is presented, with calm waters stretching toward the horizon. A wooden pier extends into the bay, surrounded by gentle sandy shores and smooth stones. Grassy areas blend seamlessly into the seaside landscape, creating a tranquil outdoor setting.

4.98 out of 5 average rating, 92 reviews

‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi

Top guest favourite

A view showcases a peaceful waterfront scene with a flagpole and vibrant grassy area in the foreground. The water reflects a bright sky filled with clouds, while a tree adds natural interest to the landscape. Nearby structures are visible along the water's edge.

4.98 out of 5 average rating, 42 reviews

Island Oasis 4+ acre waterfront house with hot tub

Destinations to explore