Deal Island Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Deal Island

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (9)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!

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

2.0 star property
9.8 out of 10, Exceptional, (8)
"Very clean and charming home we will be back again! "
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

Quaint Island Getaway

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

1 Mi to Boat Ramp: Peaceful Deal Island Home!

6.0 out of 10, (1)
"Bath tub barely drained. ankle deep water during shower. Prefer that host use vrbo site to communicate and not text or call my cell directly. Pool was nice"
1 Mi to Boat Ramp: Peaceful Deal Island Home!

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"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!

Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

10.0 out of 10, Exceptional, (1)
"The home was beautiful, the owner was lovely, and the views were spectacular. If you like spending your days on the dock and your nights surrounded by a gorgeous colorful home this is the place for you! "
Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

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

3.0 star property
10.0 out of 10, Exceptional, (2)
"The most well stocked property we've ever stayed! everything from extra phone chargers to blankets, tons of games and the kitchen as well."
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

1 Mi to Boat Ramp: Peaceful Deal Island Home!

3.0 star property
1 Mi to Boat Ramp: Peaceful Deal Island Home!

Waterfront Maryland Retreat w/ Dock & Bay View!

3.0 star property
Waterfront Maryland Retreat w/ Dock & Bay View!

Tangier Escape, great place get away from it all on Deal Island, MD.

The price is AU$316
includes taxes & fees
13 Aug - 14 Aug
Tangier Escape, great place get away from it all on Deal Island, MD.

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (75)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Cottage near the Bay

9.0 out of 10, Wonderful, (38)
"First time trying this style rental and I’m absolutely happy with the decision. The host was very accommodating and available to answer questions I had plenty of local information on hand to do things very family-friendly fun. "
The price is AU$295
includes taxes & fees
5 Aug - 6 Aug
Cottage near the Bay

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"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!

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (20)
"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

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is AU$489
includes taxes & fees
11 Aug - 12 Aug
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

9.0 out of 10, Wonderful, (2)
"very clean and neat, quiet. just what i needed"
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

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

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10.0 out of 10, Exceptional, (48)
"The house was exactly how the pictures showed !Cute and cozy ,and clean ! Im a country girl and felt at home sitting on the porch,enjoying the breeze. The sound of the ocean was a bonus!! Quiet and peaceful. I enjoyed the beautiful sunrises and morning walk on the dock. Overall i enjoyed my stay appreciate the hospitality of the host and would booked again !! "
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

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

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (17)
"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Deal Island Hotel Reviews

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?

Quaint Island Getaway: This highly rated holiday home rental in Deal Island is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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?

Rock Island and Crab 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.