List your Property
Deal Island, Maryland, United States of America

Deal Island holiday lettings

We found 21 holiday rentals — enter your dates for availability

Discover a selection of 21 holiday rentals in Deal Island, MD, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including private pool and pool. Prices start at £ 109 per night, and cottages and houses are popular options for a stay in Deal Island. Either way, you'll find a rental for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency

Find the best place to stay — Deal Island

Deal Island Bay Cottage

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
£ 122 avg/night
(23)

Renovated home w/garden on water w/great Chesapeake Bay views, quiet street.

Sleeps 5 · 2 Bedrooms · 1 Bathroom
£ 113 avg/night
(16)

The Relax-Inn Deal Island with Kayaks and Canoe

Sleeps 8 · 4 Bedrooms · 1 Bathroom
£ 109 avg/night
(36)

Waterfront,Relax,Recharge,Getaway/Bird/Fish/Paddle/Beach/Stargaze,screen-porch

Sleeps 7 · 3 Bedrooms · 2 Bathrooms
£ 218 avg/night
(6)

Paradise Awaits........

Sleeps 13 · 5 Bedrooms · 2 Bathrooms
£ 375 avg/night
(16)

Secluded Private Mansion Estate's 'Bayhouse' - 5 Bedroom / 3 Bath Guest House

Sleeps 10 · 5 Bedrooms · 3 Bathrooms
£ 904 avg/night
(33)

Search 21 holiday rentals

Top rated rentals — Deal Island
Stayed Jun 2021

Awesome!

The house is very cute, and the hosts are extremely helpful!!! The walk to the beach is muck-y but you will see a ton of wildlife along the way which we found awesome. The beach was perfect - calm waters and lots of shells to collect. We also went “c...

Karen P.
Karen P.
Stayed May 2021

Great House with a Fantastic View

Our experience at this property couldn't have been better. The house was in pristine condition upon arrival... and the legend is true... there is a pint of local ice cream waiting in the freezer! The owner went above and beyond to ensure we had every...

Kenneth W.
Kenneth W.
Stayed May 2021

Perfect location, good house, terrible weather!

We booked this house for a change of pace (slower) vacation. It afforded us the room and privacy for a group of 9. The house is very large with numerous bedrooms and baths. As we had multiple couples, we needed bedrooms with doors, as opposed to othe...

Ross V.
Ross V.

Chalfont,PA USA

Stayed May 2021

Beautiful Garden - Great for the Dog too

The cottage was very nice. The fenced garden was great for us and the dog!. If you are into boating/water adventures, this is a great location. The bedrooms are a little small and the dining room is very dark when the sun goes down. This is a complet...

Tammy B.
Tammy B.
Stayed Apr 2021

Long weekend

We had a relaxing time at the cottage. We were lucky in that the main house was not rented, so we had use of the entire property. The grounds are large enough and surrounded by water on 3 sides, so we very comfortable leaving our dogs (mostly) off th...

Gregory M.
Gregory M.
Stayed Mar 2021

Winter-Spring getaway on the Naticoke

Our stay at Jay’s river/bayside house was perfect. The house is open and airy with week equipped kitchen and comfortable beds with many thoughtful amenities like Durologs for the fire (a few chilly nights match with some warm days during our 10 day w...

Tim H.
Tim H.
Stayed Oct 2020

Quiet area - spectacular views when driving around the area.

This was the perfect place to get away for a long weekend. With the exception of a small store at the end of the island, you need to drive >20 minutes to get to restaurants and food stores. The home was clean and quiet. We saw two whitetail bucks whi...

David P.
David P.

Woodbine, MD

Stayed Sep 2020

Secluded getaway

This house is even more beautiful than the pictures suggest. It’s very much a secluded getaway, great for COVID social distancing which was just what we wanted. There isn’t a dock but the back yard is right on the water and while it was too chilly to...

Rebecca C.
Rebecca C.
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Destination guide

Relaxing Deal Island will entice you

The island views and other outdoor surroundings create an inviting atmosphere in Deal Island. This city is relaxing and walkable, recognised for its seafood restaurants, fishing and bars. If you're looking for accommodation options with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

How to get there

How to get to and around Deal Island

The nearest airport is in Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), located 26.7 mi (42.9 km) from the city centre.

Can I find a vacation rental around Deal Island?

Yes, our 2021 property listings offer a large selection of 21 vacation rentals near Deal Island. From 3 cottages to 16 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Deal Island for a holiday or a weekend are on Vrbo.

Can I rent Cottages in Deal Island?

Yes, of course. Vrbo UK has 3 Cottages in Deal Island. Our other popular types of vacation rentals in Deal Island include:

  • Houses: 16 rentals available
  • Cabins: 3 rentals available
  • Bungalows: 3 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bed & breakfasts and more.

Can I find a vacation rental with pool in Deal Island?

Yes, you can select your preferred vacation rental with pool among our 6 vacation rentals with pool available in Deal Island. Please use our search bar to access the selection of vacation rentals available.