Deal Island Vacation Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Vacation Rentals in Deal Island

Deal Island Bay Cottage

9.8 out of 10, Exceptional, (56)
"We got every year and stay here, it’s great! "
The price is CA $223
CA $393 total
includes taxes & fees
Apr 12 - Apr 13
Deal Island Bay Cottage

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

2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house, attentive host, and a beautiful and quiet setting"
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

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!

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

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"Perfect home for family gathering. Kitchen well equipped with all appliances and condiments. Bedrooms clean, with comfortable beds and linens. Beautiful views from the screened porch in backyard of Tanger Sound and colorful sunsets in hues of red, orange and yellow. Quick communication with owner. Would definitely stay again!"
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

1 Mi to Boat Ramp: Peaceful Deal Island Home!

1 Mi to Boat Ramp: Peaceful Deal Island Home!

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

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

Cottage near the Bay

8.8 out of 10, Excellent, (30)
"Great time"
The price is CA $129
CA $282 total
includes taxes & fees
Mar 26 - Mar 27
Cottage near the Bay

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (66)
"the Hoopers Island area is amazingly wild and beautiful. we loved the Harriet Tubman visitors center just a short trip away, and the Blackwater Refuge just incredibly beautiful. the winter birds! we learned so much about the history and culture of the lower islands.the house is more cabin style, smaller than we anticipated, but we got used to that. it was full-on winter weather and wind, so we couldn't kayak as we'd hoped, and the coast was mostly rocks so hard to walk along. it's a place for...
Waterfront Cottage in Beautiful Hoopers Island

Dog-Friendly Westover Cottage w/ River Access!

9.8 out of 10, Exceptional, (7)
"Overall very good. Bath/shower needs upgrade Gas fireplace hard to start. May need maintenance Very pet friendly. Dog bowls, bed, and toys on site Owner allowed early arrival and was responsive quickly to any questions that we had "
Dog-Friendly Westover Cottage w/ River Access!

The Schultz Estate

8.4 out of 10, Very good, (15)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate

Home in the Heart of Salisbury 3BR 4 Beds Sleeps 8 Blocks from SU and Downtown

10.0 out of 10, Exceptional, (9)
"Our own home was too small for our growing family. The rental allowed our adult children to be home for the holidays comfortably. Perfect location and close to “home base”.Will use again in the future!!!! "
Home in the Heart of Salisbury 3BR 4 Beds Sleeps 8 Blocks from SU and Downtown

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

10.0 out of 10, Exceptional, (5)
"The hot tube was a great for relaxing and looking at the many stars seen without light pollution. The dock made me want to cast a line and relax. I'd stay there again and extend my visit!"
Secluded waterfront getaway with hot tub,fire pit, and private dock.

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (9)
"Listing and photos accurately describe accommodations. We were comfortable and satisfied. A nice rural location for perusing outdoor activities - fishing, hunting, boating, paddling, birdwatching. Good parking for a boat trailer. "
The Blackwater refuge country house on a quiet 12 acres

Single family home with screened porch.

10.0 out of 10, Exceptional, (11)
"Stayed for a week while hunting with my buddy. It had everything we needed to be comfortable and cook some meals. Definitely enjoyed the view from the porch."
Single family home with screened porch.

Salisbury Cottage

10.0 out of 10, Exceptional, (23)
"We were in town for our daughter’s graduation from Salisbury University. The house was very cozy and perfectly situated close to the school. It was clean and very well maintained and decorated. Our only complaint is that we weren’t able to stay longer. If you are visiting the Salisbury area I highly recommend booking this house."
The price is CA $214
CA $516 total
includes taxes & fees
Mar 16 - Mar 17
Salisbury Cottage

Historic Hoopersville Getaway on Chesapeake Bay!

9.6 out of 10, Exceptional, (10)
"We had a lovely time on this trip. The house is spacious and the yard/location is great. The kitchen needed a few more things that we could have used but overall we would definitely return. There are no stores nearby so buy everything you need before arriving. You will not regret coming to this house. We made a lot of memories and enjoyed every minute. The host was very attentive and helpful."
Historic Hoopersville Getaway on Chesapeake Bay!

Walk to Main St: Condo w/ Pool Access in Crisfield

Walk to Main St: Condo w/ Pool Access in Crisfield

Pet-Friendly Quantico Home w/ River Views!

9.6 out of 10, Exceptional, (9)
"Well kept property with very comfortable beds! Breathtaking views of the Wicomico River!!"
Pet-Friendly Quantico Home w/ River Views!

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay
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.
Don't see what you're looking for?
See all available properties in Deal Island
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Deal Island you may be interested in

Deal Island Bay Cottage

9.8 out of 10, Exceptional, (56)
"We got every year and stay here, it’s great! "
The price is CA $223
CA $393 total
includes taxes & fees
Apr 12 - Apr 13
Deal Island Bay Cottage

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

2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house, attentive host, and a beautiful and quiet setting"
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

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!
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.

Frequently asked questions

Can I find a vacation rental in Deal Island?

Yes, we offer vacation rentals near well known sights in Deal Island, or you can go with a more secluded option if you'd like a relaxing place to stay. Deal Island is known for its beaches and seafood restaurants. Make sure you have time to check out the bars while you're in the area.

What are some of the best vacation rentals that Deal Island has to offer?

Cottage near the Bay: This vacation home rental outside of Deal Island is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Deal Island?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Deal Island stay.

What’s there to see and do in Deal Island?

Crab Island and Rock Island are a couple of lovely local spots to get outside and enjoy nature. Shark Fin Shoal and Franks Island are other places to visit while you're in town.

What’s a vacation rental in Deal Island like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Deal Island. Vacation rentals feature extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.