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Compare 24 Cottages in Deal Island with updated reviews, rates, and availability.

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (67)
"Extraordinary. Love it . "
Waterfront Cottage in Beautiful Hoopers Island

Dog-Friendly Westover Cottage w/ River Access!

9.8 out of 10, Exceptional, (9)
"Overall very good. Bath/shower needs upgrade Gas fireplace hard to start. May need maintenance Very pet friendly. Dog bowls, bed, and toys on site Owner allowed early arrival and was responsive quickly to any questions that we had "
Dog-Friendly Westover Cottage w/ River Access!

Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

10.0 out of 10, Exceptional, (47)
"The views of the bay are magnificent, sunrise and sunset. The property is spotless. Toby and Kim, the hosts, could not be more accommodating. "
Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Pet-Friendly Smith Island Cottage w/ Golf Cart!

9.8 out of 10, Exceptional, (10)
"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "
Pet-Friendly Smith Island Cottage w/ Golf Cart!

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (15)
"Micky and Kim were great hosts and the house was awesome. They were very accommodating. Will definitely be back! "
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (6)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!

Blue Heron Cottage On Smith's Island

9.8 out of 10, Exceptional, (38)
"The stay was just perfect. We came with our own boat and it was easy to navigate to the house. The dock was 30 yards from the front door so easy to get out supplies to the house. (We did make use of the golf cart 😊). Neighbors are so friendly and they let us use their phone to call our family to let them know we arrived. Our cell phones did not work as it is a bit remote. We later found out that there is some coverage on the second floor of the house😁 Nevertheless we did not miss internet and...
Blue Heron Cottage On Smith's Island

Pet-friendly Smith Island Cottage w/ Golf Cart!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
Pet-friendly Smith Island Cottage w/ Golf Cart!

Dog-friendly Westover Cottage w/ River Access!

3.0 star property
8.0 out of 10, Very Good, (1)
"It was great and family enjoyed our relaxation "
Dog-friendly Westover Cottage w/ River Access!

Tyaskin Retreat w/ Deck - Across From the Water!

2.0 star property
Tyaskin Retreat w/ Deck - Across From the Water!

Pet-friendly Quantico Home w/ River Views!

3.0 star property
Pet-friendly Quantico Home w/ River Views!

1 Mi to Boat Ramp: Peaceful Deal Island Home!

3.0 star property
1 Mi to Boat Ramp: Peaceful Deal Island Home!

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

3.0 star property
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Riverfront Gem w/ Fire Pit in Eden

3.0 star property
Riverfront Gem w/ Fire Pit in Eden

Historic Hoopersville Getaway on Chesapeake Bay!

3.0 star property
Historic Hoopersville Getaway on Chesapeake Bay!

Waterfront Maryland Retreat w/ Dock & Bay View!

3.0 star property
Waterfront Maryland Retreat w/ Dock & Bay View!

Waterfront Marion Station Retreat w/ Private Dock!

3.0 star property
Waterfront Marion Station Retreat w/ Private Dock!

Updated Home - Walk to Salisbury University!

3.0 star property
Updated Home - Walk to Salisbury University!
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.
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Other property types in Deal Island

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (6)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Perfect home for family gathering. Kitchen well equipped with all appliances and condiments. Bedrooms clean, with comfortable beds and linens. Beautiful views from the screened porch in backyard of Tanger Sound and colorful sunsets in hues of red, orange and yellow. Quick communication with owner. Would definitely stay again!"
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property
9.6 out of 10, Exceptional, (5)
"Very clean and charming home we will be back again! "
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
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.