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Featured Cottages in Deal Island

Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

Fishing Creek
Located in Fishing Creek, this cottage is on the waterfront, a 5-minute drive from P. L. Jones Marina and 6 minutes from Middle Hooper Island.
Waterfront Cottage in Beautiful Hoopers Island
Dog-Friendly Westover Cottage w/ River Access!

Dog-Friendly Westover Cottage w/ River Access!

Westover
Located in Westover, this cottage is on the waterfront, within a 15-minute drive of Great Hope Golf Course and Upper Hill Park.
Dog-Friendly Westover Cottage w/ River Access!
Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

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

Fishing Creek
Located in Fishing Creek, this cottage is on the waterfront, a 2-minute drive from P. L. Jones Marina and 6 minutes from Gunners Island.
Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣
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Near Chincoteague & Assateague Island
Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis
With a stay at this cottage in Saxis, you'll be 13.8 mi (22.3 km) from Bloxom Winery and 16.3 mi (26.2 km) from Kegotank Bay.
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Ewell
When you stay at this cottage in Smith Island, you'll be near the beach and steps from Terrapin Sand Point.
Pet-Friendly Smith Island Cottage w/ Golf Cart!
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

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

Smith Island
When you stay at this cottage in Smith Island, you'll be on the waterfront and steps from Terrapin Sand Point.
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Waterfront Maryland Retreat w/ Dock & Bay View!

Waterfront Maryland Retreat w/ Dock & Bay View!

Deal Island Historic District
Located in Deal Island, this cottage is on the waterfront, a 4-minute drive from Shark Fin Shoal and 7 minutes from Rock Island.
Waterfront Maryland Retreat w/ Dock & Bay View!
Blue Heron Cottage On Smith's Island

Blue Heron Cottage On Smith's Island

Smith Island
When you stay at this cottage in Smith Island, you'll be on the waterfront and convenient to Tylerton County Dock and Smith Island.
Blue Heron Cottage On Smith's Island
Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!

3 out of 5
Smith Island
When you stay at this cottage in Smith Island, you'll be steps from Terrapin Sand Point.
Pet-friendly Smith Island Cottage w/ Golf Cart!
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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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Deal Island will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Deal Island definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Deal Island, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Deal Island Cottages essential information

Accommodation
24 Cottages
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!

Top trending hotels in Deal Island

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

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

2 out of 5
Deal Island Historic District
Located in Deal Island, this vacation home is a 3-minute drive from Shark Fin Shoal and 6 minutes from Rock Island.
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
Waterfront Maryland Retreat w/ Dock & Bay View!

Waterfront Maryland Retreat w/ Dock & Bay View!

Deal Island Historic District
Located in Deal Island, this cottage is on the waterfront, a 4-minute drive from Shark Fin Shoal and 7 minutes from Rock Island.
Waterfront Maryland Retreat w/ Dock & Bay View!
Quaint Island Getaway

Quaint Island Getaway

Deal Island Historic District
When you stay at this vacation home in Deal Island, you'll be near the beach and 7 minutes by car from Shark Fin Shoal.
Quaint Island Getaway
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Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

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

2 out of 5
Deal Island Historic District
Located in Deal Island, this vacation home is a 4-minute drive from Shark Fin Shoal and 7 minutes from Rock Island.
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
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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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