Deal Island Holiday Rentals

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Holiday 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 AU$439
includes taxes & fees
19 Feb - 20 Feb
Deal Island Bay Cottage

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!

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

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

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

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

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

2.0 star property
Par-Lon - Private Raised Waterfront Home on the Pocomoke River

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

Cottage near the Bay

8.8 out of 10, Excellent, (29)
"Great time"
The price is AU$314
includes taxes & fees
18 Feb - 19 Feb
Cottage near the Bay

Beautiful Bayfront with Sanctuary Private Beach

9.0 out of 10, Wonderful, (17)
"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

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!

10.0 out of 10, Exceptional, (6)
"As a mom of two , one with Tourette’s and comorbidies that go with it, relaxing getaways are few and far between. This was just what the doctor ordered. Kayaking, fishing, nature walks!! "
Dog-Friendly Westover Cottage w/ River Access!

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!

Waterfront Marion Station Retreat w/ Private Dock!

8.6 out of 10, Excellent, (4)
"Home offers breathtaking views of the bay. Plenty of space for two families with children. Would love to come back!"
Waterfront Marion Station Retreat w/ Private Dock!

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 AU$549
includes taxes & fees
18 Feb - 19 Feb
Salisbury Cottage

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

10.0 out of 10, Exceptional, (4)
"The house was clean, in a quiet location, and we appreciated the attention to the little details from the property owners. We had a beautiful view of the creek and have already re-booked the house for another stay. "
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.

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.
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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 AU$439
includes taxes & fees
19 Feb - 20 Feb
Deal Island Bay Cottage

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!

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 holiday rental in Deal Island?

Yes, there are holiday rentals close to the most popular sights in Deal Island, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Deal Island has to offer?

Paradise Awaits........: This holiday home rental outside of Deal Island is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Deal Island?

With 5 Expedia holiday rentals, you're guaranteed 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 holiday rental in Deal Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Deal Island. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.