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Featured Cottages in Deal Island

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is AU$371
includes taxes & fees
7 Jan - 8 Jan 2025
Deal Island Bay Cottage

Dog-Friendly Westover Cottage w/ River Access!

10.0 out of 10, Exceptional, (6)
"As a mom of two , one with Tourette’s and comorbidies that go with it, relaxing getaways are few and far between. This was just what the doctor ordered. Kayaking, fishing, nature walks!! "
Dog-Friendly Westover Cottage w/ River Access!

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (65)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island

Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

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

10.0 out of 10, Exceptional, (14)
"The house is great, so clean and well-equipped and has everything you need for a comfortable stay. Kim delivered delicious crabs right to the dinner table! We enjoyed riding the bikes around the island. Smith Island Bakery is only a few doors down!"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!

10.0 out of 10, Exceptional, (5)
"The cottage is absolutely perfect! The decor is perfect, the amenities were thoughtful, and the house was immaculate! It was convenient to everything in town. The hosts were wonderful, friendly, knowledgeable and responded quickly to messages. We loved our stay and would definitely visit again!"
The price is AU$294
includes taxes & fees
31 Dec - 1 Jan 2025
BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!

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 Quantico Home w/ River Views!

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

Dog-friendly Westover Cottage w/ River Access!

3.0 star property
Dog-friendly Westover Cottage w/ River Access!

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!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

9.8 out of 10, Exceptional, (9)
"great but high tide problems to limit activity"
Pet-Friendly Smith Island Cottage w/ Golf Cart!

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!

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

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!

Historic Hoopersville Getaway on Chesapeake Bay!

3.0 star property
Historic Hoopersville Getaway on Chesapeake Bay!

Tyaskin Retreat w/ Deck - Across From the Water!

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

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

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

Tyaskin Retreat w/ Deck - Across From the Water!

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

Waterfront Maryland Retreat w/ Dock & Bay View!

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

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is AU$371
includes taxes & fees
7 Jan - 8 Jan 2025
Deal Island Bay Cottage

Quaint Island Getaway

10.0 out of 10, Exceptional, (13)
"Staying at the Quaint Island Getaway is always a pleasure! Sarah is an accessible host, the property is cozy and clean. My party loved the new firepit."
Quaint Island Getaway

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our stay was perfect. The home was quite lovely and equipped with all amenities. The location was very nice. The bay was only a 2 minute walk at the end of the street. Highly recommend."
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.