Holiday Homes in Deal Island

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Deal Island and around

Cottage near the Bay
Dining

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is €165
includes taxes & fees
14 Aug - 15 Aug
Cottage near the Bay
Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!
Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP
Interior

Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is €276
includes taxes & fees
14 Aug - 15 Aug
Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP
Hoopers Island Retreat
WiFi, bed sheets

Hoopers Island Retreat

Hoopers Island Retreat
Beautiful Bayfront with Sanctuary Private Beach
Property grounds

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (20)
"The property is beautiful and it was so nice to be so close to the water. Sunset view and fire pit out back were fun bonuses. Everything went smoothly and as expected. We enjoyed our stay, thank you!"
Beautiful Bayfront with Sanctuary Private Beach
Walk to Main Street: Family-Friendly Crisfield Gem
Fridge, microwave, stovetop, dishwasher

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (2)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem
The Blackwater refuge country house on a quiet 12 acres
Property grounds

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (10)
"Very happy with this place, quiet, clean, all good. "
The Blackwater refuge country house on a quiet 12 acres
Secluded waterfront getaway with hot tub,fire pit, and private dock.
Outdoor spa tub

Secluded waterfront getaway with hot tub,fire pit, and private dock.

10.0 out of 10, Exceptional, (8)
"This is such a lovely place for families to unwind and enjoy time together!"
Secluded waterfront getaway with hot tub,fire pit, and private dock.
Home in historic Whitehaven Village.
Fridge, microwave, oven, stovetop

Home in historic Whitehaven Village.

10.0 out of 10, Exceptional, (4)
"Great stay! Nice and relaxing and owner fast response with questions!"
Home in historic Whitehaven Village.
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Dining

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

2.0 star property
9.8 out of 10, Exceptional, (8)
"Very clean and charming home we will be back again! "
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Salisbury Cottage
Fridge, microwave, oven, stovetop

Salisbury Cottage

10.0 out of 10, Exceptional, (27)
"Cleanliness of property. Location. Everything g was perfect for our golf/lacrosse getaway"
The price is €341
includes taxes & fees
20 Aug - 21 Aug
Salisbury Cottage
Riverfront Gem w/ Fire Pit in Eden
Fridge, microwave, stovetop, dishwasher

Riverfront Gem w/ Fire Pit in Eden

10.0 out of 10, Exceptional, (1)
"We srayed at this property due to number of guests and proximity to the college. It was a great mix of old and new. This house was wonderfully appointed and everyone enjoyed their stay. The views were spectacular and we had everything we needed and more. It was unexpectedly remote, but once we got used to it, it was barely noticeable. We are even considering staying here again "
Riverfront Gem w/ Fire Pit in Eden
Historic Hoopersville Getaway on Chesapeake Bay!
Dining

Historic Hoopersville Getaway on Chesapeake Bay!

9.6 out of 10, Exceptional, (13)
"I really can’t say enough about this place! The house has so much charm! The island is very quiet! Great place to just get away and spend quality time with your family! Can’t wait to go back!"
Historic Hoopersville Getaway on Chesapeake Bay!
The Schultz Estate
Outdoor dining

The Schultz Estate

7.0 out of 10, Good, (21)
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
The Schultz Estate
Par-Lon - Private Raised Waterfront Home on the Pocomoke River
Property grounds

Par-Lon - Private Raised Waterfront Home on the Pocomoke River

2.0 star property
10.0 out of 10, Exceptional, (3)
"Had an amazing time here very piecefull and beautiful "
Par-Lon - Private Raised Waterfront Home on the Pocomoke River
Cottage on the Bay
Outdoor dining

Cottage on the Bay

9.8 out of 10, Exceptional, (8)
"good place to fish good place to enjoy with family quiet and very clean place"
Cottage on the Bay
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!
Outdoor dining

BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!

10.0 out of 10, Exceptional, (63)
"A wonderful long weekend getaway on Hoopers Island--close to the bay and to the attractions of the island. Laura is a great host who ensured we had everything we needed for our stay--a roomy house with a great screened in gazebo and plenty of activities for our elementary school aged kids. Highly recommend it!"
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!
Bayfront Beauty with Beach and Boatslip!!
Smart TV, fireplace

Bayfront Beauty with Beach and Boatslip!!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Highly recommend, very communicative host, the place is better than shown. Great views, private boat slip. The community right next to it is nice with a little local pub. "
Bayfront Beauty with Beach and Boatslip!!
Quaint Island Getaway
Beach nearby, sun-loungers

Quaint Island Getaway

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay. The property was clean and cozy."
Quaint Island Getaway
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Exterior

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

10.0 out of 10, Exceptional, (11)
"Had such an enjoyable time over the weekend with the gracious hosts Peggy and Gary. Tidy and clean property in a beautiful area. Great food and great company. Definitely recommend for anyone looking for a nice peaceful getaway."
The price is €288
includes taxes & fees
19 Aug - 20 Aug
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
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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Top Deal Island Hotel Reviews

The Whitehaven Hotel

The Whitehaven Hotel

10/10 Excellent
"Perfect in every way. You won’t get a warmer welcome anywhere and the hotel is so full of character and comfort. Beautiful spot to relax, take in the beautiful scenery, watch ospreys, go to the beach, kayak, visit vineyards … or just take a book and sit on the deck!"
Elin 2-night trip
Posted 3 days ago
The Whitehaven Hotel