A beach with several boats and people fishing.

Deal Island Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Deal Island holiday rentals

Interior

Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
Pet-friendly Smith Island Cottage w/ Golf Cart!
Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is S$1,180
includes taxes & fees
29 Jul - 30 Jul
'the Bayside Escape' Remote Chesapeake Bay Estate
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Deal Island Hotel Reviews

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

10/10 Excellent
"Clean room, good customer service, good stay."
Karen 2-night trip
Posted 6 hours ago
Best Western Plus Pocomoke City

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.

How many holiday rentals will I find in Deal Island?

With 9 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. Franks Island and Shark Fin Shoal 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.