Top Deal Island Holiday Cottages in 2025
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Featured Cottages in Deal Island
Waterfront Cottage in Beautiful Hoopers Island
During your stay at this cottage, you'll be close to P. L. Jones Marina. The cottage offers free WiFi and a kitchen.
Kitchen
Pet-friendly
Dog-Friendly Westover Cottage w/ River Access!
During your stay at this cottage, you'll be close to Upper Hill Park. Features include laundry facilities. The cottage offers a kitchen and a patio.
Kitchen
Washer
Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣
During your stay at this cottage, you're just a quick walk from P. L. Jones Marina. The cottage includes amenities such as free WiFi and a kitchen.
Kitchen
Pet-friendly
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
During your stay at this cottage, you'll be close to Langford Sand. Laundry facilities are available. The cottage includes amenities such as free WiFi and a kitchen.
Kitchen
Washer
Pet-Friendly Smith Island Cottage w/ Golf Cart!
During your stay at this cottage, you're just a quick walk from Terrapin Sand Point. Enjoy features like laundry facilities. A kitchen and a TV are available in the cottage.
Kitchen
Washer
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
During your stay at this cottage, you're just a quick walk from Terrapin Sand Point. Enjoy features like laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the cottage.
Kitchen
Washer
Waterfront Maryland Retreat w/ Dock & Bay View!
During your stay at this cottage, you'll be close to Rock Island. You'll find features such as laundry facilities. Enjoy your stay with amenities like a kitchen and 2 bathrooms in the cottage.
Kitchen
Washer
Blue Heron Cottage On Smith's Island
During your stay at this cottage, you'll be close to Tylerton County Dock. You'll find features such as laundry facilities. Enjoy your stay with amenities like a kitchen and a TV in the cottage.
Kitchen
Washer
Pet-friendly Smith Island Cottage w/ Golf Cart!
During your stay at this cottage, you're just a quick walk from Terrapin Sand Point. You'll find features such as free WiFi in public areas, plus a marina and an arcade/games room. The cottage offers a kitchen and a TV.
Kitchen
Pet-friendly
Dog-friendly Westover Cottage w/ River Access!
During your stay at this cottage, you'll be close to Upper Hill Park. Features include free WiFi in public areas and free self-parking. The cottage offers a kitchen and a TV.
Kitchen
Pet-friendly
1 Mi to Boat Ramp: Peaceful Deal Island Home!
During your stay at this cottage, you'll be close to Rock Island. Free WiFi in public areas, free self-parking and an outdoor pool are available. A kitchen and a microwave are available in the cottage.
Pool
Kitchen
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
During your stay at this cottage, you'll be close to Rock Island. Features include free WiFi in public areas and free self-parking. The cottage offers a kitchen and 2 bathrooms.
Kitchen
Pet-friendly
Riverfront Gem w/ Fire Pit in Eden
During your stay at this cottage, you'll be close to Bordeleau Winery. Free WiFi in public areas, free self-parking and a marina are available. The cottage offers a kitchen and 3.5 bathrooms.
Kitchen
Parking included
Historic Hoopersville Getaway on Chesapeake Bay!
During your stay at this cottage, you'll be within walking distance of Lower Hooper Island. Features include free WiFi in public areas and free self-parking. The cottage includes amenities such as a kitchen and 2.5 bathrooms.
Kitchen
Pet-friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Deal Island Cottages essential information
Accommodation | 23 Cottages |
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Lowest Price | |
Highest Price | |
Popular accommodation | Waterfront Cottage in Beautiful Hoopers Island, Dog-Friendly Westover Cottage w/ River Access!, Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣, Near Chincoteague & Assateague Island Charming 2-bedroom cottage, Pet-Friendly Smith Island Cottage w/ Golf Cart!, IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK, Waterfront Maryland Retreat w/ Dock & Bay View!, Blue Heron Cottage On Smith's Island, Pet-friendly Smith Island Cottage w/ Golf Cart!, Dog-friendly Westover Cottage w/ River Access!, 1 Mi to Boat Ramp: Peaceful Deal Island Home!, Maryland Retreat: Walk to Bay, Beach & Boat Ramp!, Riverfront Gem w/ Fire Pit in Eden, Historic Hoopersville Getaway on Chesapeake Bay!, Waterfront Maryland Retreat w/ Dock & Bay View! |
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