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Vacation Homes in Deal Island

Our top choices for Deal Island vacation homes

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
$178 nightly
The price is $189
Sep 1 - Sep 2
Total with taxes and fees
Cottage near the Bay

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"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!

Single family home with screened porch.

10.0 out of 10, Exceptional, (12)
"The house was very nicely done and extremely well stocked and the host was very friendly and super easy to deal with. We especially like the location for sunrise walks with the dogs and easy access to the national parks. "
Single family home with screened porch.

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

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

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
$326 nightly
The price is $346
Aug 29 - Aug 30
Total with taxes and fees
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

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

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

Century-old home with fenced yard, great front porch & small-town charm

9.8 out of 10, Exceptional, (7)
"The inside of the home was very clean with cute decor."
Century-old home with fenced yard, great front porch & small-town charm

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.

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

Fully furnished 3-bedroom house sporting Queen-size beds in each room

7.4 out of 10, Good, (3)
"We arrived after 11:00 PM and would have left as soon as we walked in but the nearest vacancy was over an hour and 1/2 away and we were traveling with a child who was exhausted. We cut the stay here short and left first thing the next morning. If you are interested in staying in a dirty, creepy, smelly house with urine stains on the floor and bugs, this is the right place. Filthy! Most of the furniture looks like it was pulled randomly from the trash. An experience we will never forget. "
Fully furnished 3-bedroom house sporting Queen-size beds in each room

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.

Salisbury Cottage

10.0 out of 10, Exceptional, (27)
"This property was very convenient to everything we needed. It was clean and well equipped and the hosts could not have been nicer or more attentive. We would definitely stay there again. Thank you for a wonderful stay."
$323 nightly
The price is $359
Sep 2 - Sep 3
Total with taxes and fees
Salisbury Cottage

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (21)
"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

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"The house was beautiful and our stay was great. Looking forward to future visits. "
Par-Lon - Private Raised Waterfront Home on the Pocomoke River

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!!

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

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay. The property was clean and cozy."
Quaint Island Getaway

Hoopers Island Retreat

8.0 out of 10, Very Good, (1)
"Beautiful view!"
Hoopers Island Retreat

Waterfront Historic Gem w/ Kayaks & Fire Pit

8.8 out of 10, Excellent, (3)
"Great house. Clean. Had everything we needed."
Waterfront Historic Gem w/ Kayaks & Fire Pit
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

Find out more about Deal Island

Find out more about Deal Island

Deal Island Vacation Homes information

Number of reviews
122
Accommodation
57 Vacation Homes
Lowest Price
$189
Highest Price
$359

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