Book Holiday Homes in Deal Island

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Featured Holiday Homes in Deal Island

Cottage near the Bay

Cottage near the Bay

Crisfield
The price is NZ$314 per night from 29 Sept to 30 Sept
NZ$314
29 Sept - 30 Sept
includes taxes & fees
Stay at this vacation home in Crisfield. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Gov. Tawes Library and Crisfield ...
Opens in a new windowCottage near the Bay
Single family home with screened porch.

Single family home with screened porch.

Fishing Creek
Stay at this vacation home in Fishing Creek. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions P. L. Jones Marina and Gunners Island are ...
Opens in a new windowSingle family home with screened porch.
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island
Stay at this vacation home in Smith Island. Enjoy a garden, laundry facilities, and patios. Popular attractions Smith Island and Tylerton County Dock are located ...
Opens in a new windowHistoric home on Smith Island w/ dock!
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The Blackwater refuge country house on a quiet 12 acres

The Blackwater refuge country house on a quiet 12 acres

Crapo
Stay at this vacation home in Cambridge. Enjoy a garden, laundry facilities, and air conditioning. Popular attractions Blackwater National Wildlife Refuge and ...
Opens in a new windowThe Blackwater refuge country house on a quiet 12 acres
Walk to Main Street: Family-Friendly Crisfield Gem

Walk to Main Street: Family-Friendly Crisfield Gem

Crisfield
Stay at this vacation home in Crisfield. Enjoy laundry facilities, cable/satellite TV service, and in-room fireplaces. Popular attractions Gov. Tawes Library ...
Opens in a new windowWalk to Main Street: Family-Friendly Crisfield Gem
Beautiful Bayfront with Sanctuary Private Beach

Beautiful Bayfront with Sanctuary Private Beach

Saxis
Stay at this vacation home in Saxis. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Langford Sand and Big Island are located ...
Opens in a new windowBeautiful Bayfront with Sanctuary Private Beach
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Smith Island
The price is NZ$587 per night from 20 Sept to 21 Sept
NZ$587
20 Sept - 21 Sept
includes taxes & fees
Stay at this vacation home in Smith Island. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Smith Island and Tylerton County Dock are located ...
Opens in a new windowKayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Waterfront Historic Gem w/ Kayaks & Fire Pit

Waterfront Historic Gem w/ Kayaks & Fire Pit

Quantico
Stay at this vacation home in Quantico. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Whitehaven Historic District and Mount Vernon Park ...
Opens in a new windowWaterfront Historic Gem w/ Kayaks & Fire Pit
Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres

Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres

2 out of 5
Vienna
Book a stay at this beach vacation home in Vienna. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Elliott Island and Sandy Island ...
Opens in a new windowFabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres
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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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Deal Island vacation homes are the perfect way for you to wing it.

Holiday houses in Deal Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Deal Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Deal Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Deal Island with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Deal Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Deal Island Holiday Homes essential information

Accommodation
57 Holiday Homes
Lowest Price
NZ$314
Highest Price
NZ$587
Popular accommodation
Cottage near the Bay, Single family home with screened porch. , Historic home on Smith Island w/ dock!, The Blackwater refuge country house on a quiet 12 acres, Walk to Main Street: Family-Friendly Crisfield Gem, Beautiful Bayfront with Sanctuary Private Beach , Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart, Waterfront Historic Gem w/ Kayaks & Fire Pit, Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres

Top trending hotels in Deal Island

Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island
The price is NZ$444 per night from 20 Sept to 21 Sept
NZ$444
20 Sept - 21 Sept
includes taxes & fees
Stay at this cottage in Deal Island. Enjoy free WiFi, laundry facilities, and cable/satellite TV service. Popular attractions Rock Island and Crab Island are ...
Opens in a new windowDeal Island Bay Cottage
Quaint Island Getaway

Quaint Island Getaway

Deal Island Historic District
Stay at this vacation home in Deal Island. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Rock Island and Crab Island are located ...
Opens in a new windowQuaint Island Getaway
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

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

3 out of 5
Deal Island
Stay at this 3-star business-friendly cottage in Deal Island. Enjoy free parking, a computer station, and air conditioning. Popular attractions Rock Island and ...
Opens in a new windowMaryland Retreat: Walk to Bay, Beach & Boat Ramp!
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Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

Deal Island Historic District
Stay at this vacation home in Deal Island. Enjoy a garden, laundry facilities, and patios. Popular attractions Rock Island and Crab Island are located ...
Opens in a new windowReel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District
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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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^Subject to availability and chosen travel dates.