Cobb Island vacation rentals
Find spaces that suit your style
Find the best place to stay - Cobb Island
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Top rated rentals - Cobb Island
Photo gallery for Sunnyside Up - Small Dog Friendly Waterfront Cottage
Second time around
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Find the perfect vacation rental for your Cobb Island getaway
Experience the unique character of Cobb Island with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.
Sightseeing in and around Cobb Island
Are you searching for attractions to see while you're in town? Venture out of your cozy vacation rental and experience everything that makes Cobb Island a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:
- Maryland International Raceway (9.9 mi / 15.9 km)
- Ingleside Vineyards (11.7 mi / 18.9 km)
- Caledon State Park (17.8 mi / 28.6 km)
- Port of Leonardtown Winery (10.6 mi / 17.1 km)
- Ingleside Vineyards (11.4 mi / 18.4 km)
- Cameron Hills Golf Links (14.9 mi / 24 km)
Exploring the natural landscape of Cobb Island
Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Cobb Island is a great place to spend some time outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:
- Colonial Beach (6.4 mi / 10.2 km)
- Westmoreland State Park (7.4 mi / 11.8 km)
- St. Mary's River State Park (15.9 mi / 25.6 km)
- Caledon State Park (17.8 mi / 28.6 km)
- Rappahannock River Valley National Wildlife Refuge (18.3 mi / 29.4 km)
- St. Clement's Island State Park (6.1 mi / 9.8 km)