Holiday Rentals in Deal Island

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Holiday Rentals in Deal Island

Quaint Island Getaway
10.0 out of 10, Exceptional, 11 reviews
"This is a charming place, full of really nice interior touches. The location gives you access to some great marshland so you are treated to a daily dose of great bird sightings, including ospreys, red-winged blackbirds, herons and others. The house has everything you need. The only advice I would give - to remind guests to clean off the grill when they are done using it. We had to clean it thoroughly as it had obviously not been cleaned in awhile. I suggest you add that to the short list of...
Quaint Island Getaway
Waterfront Maryland Retreat w/ Dock & Bay View!
10.0 out of 10, Exceptional, 1 review
"I was a little hesitant about this Vrbo since there were no reviews but the house was exactly as described. We wanted a quiet, do nothing but relax and that is what we did. We loved the private dock and caught many crabs and a few fish. The bay breeze kept the bugs away which was an added bonus. The little beach over the bridge was great for a quick dip to cool off (although the bay was 82). We also chartered a fishing boat with a local company (art benton) who gave us a great day on the water...
Waterfront Maryland Retreat w/ Dock & Bay View!
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, 56 reviews
"This is a unique property with expansive water views. Quiet neighborhood with wonderful and helpful caretakers. We spent 3 nights with our 5 month old puppy and thoroughly enjoyed it. Had dinner in 2 nights and went to Old Salty’s one night for crabcakes. Very good service and great food. Brought our boat and had a great time. The cottage was immaculate and extremely well equipped."
Waterfront Cottage in Beautiful Hoopers Island
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Riverfront Cabin Getaway at The Brackish - Pet Friendly!
2.0 star property
8.0 out of 10, Very good, 1 review
"Outstanding views Comfortable beds Homey atmosphere and decorated impeccably! Convenient to family and friends Despite heat, kept cool with AC and a “ dip” in the river! Great time was had by all!"
Riverfront Cabin Getaway at The Brackish - Pet Friendly!
Simply the best...Beautiful condo overlooking the Chesapeake bay.
10.0 out of 10, Exceptional, 103 reviews
"This condo was one of the nicest places I have ever stayed. Very, very clean, beautiful view of the bay, everything we needed, kitchen very well supplied. Friendly people we met at the condo, great parking and also nice and quiet in the evenings. We'll be back, I highly recommend this condo for anyone looking for a getaway weekend or whatever."
Simply the best...Beautiful condo overlooking the Chesapeake bay.
The Schultz Estate
9.8 out of 10, Exceptional, 7 reviews
"We held a family reunion at the house with 11 adults ranging in age from 55 to 90. We were interested in the area for its surrounding attractions We chose the house because of its curb appeal, the number of bedrooms it offers, and very reasonable price. The house has the requisite number of bedrooms and plentiful space for people to cook, eat and spend time together, both inside and outside. Of the three bathrooms, the two with showers are upstairs and in high demand, which was our only...
The Schultz Estate
Beautiful Bayfront with Sanctuary Private Beach
8.8 out of 10, Excellent, 13 reviews
"Nice, relaxing stay!"
The price is €410
includes taxes & fees
18 Jul - 19 Jul
Beautiful Bayfront with Sanctuary Private Beach
Historic Hoopersville Getaway on Chesapeake Bay!
9.6 out of 10, Exceptional, 9 reviews
"Our vacation on Chesapeake Bay was wonderful. The house was clean and comfortable. It is an older home, but we loved the character and charm. There is a very large yard for playing, bikes and some board games/puzzles that we enjoyed. The island was very quiet so made for a relaxing vacation. The home came with kayaks, and we had a blast kayaking with our 2 and 4 year old on the ocean. I would highly recommend this home for a big gathering or small family like our trip. We felt so rested after...
Historic Hoopersville Getaway on Chesapeake Bay!
Cottage near the Bay
8.8 out of 10, Excellent, 15 reviews
"The owner was quick to respond, informative, and polite. The property did the job we were asking from it by being near by our family, close to the bay, and being pet friendly. I was not impressed by the cleanliness, but it was not out right dirty or unsanitary. You get what you pay for. Over all we were pleased with our stay!"
The price is €189
includes taxes & fees
18 Jul - 19 Jul
Cottage near the Bay
Waterfront 3 bedroom condo. Summer has arrived, pool is open!
10.0 out of 10, Exceptional, 23 reviews
"Very relaxing"
Waterfront 3 bedroom condo. Summer has arrived, pool is open!
Historic home on Smith Island w/ dock!
9.6 out of 10, Exceptional, 31 reviews
"During our stay at The Pearl, we encountered our own boat issues, but the hosts were extremely helpful. Their communication was above and beyond!! The people on the island were also extremely helpful, and they went out of their way to help in any way they could. They all truly wanted us to have a great experience on Smith Island. The Pearl had everything we needed for our stay, and there was plenty of room for us. We took our pet Corgi and she felt right at home and loved the big yard! We CANNOT...
Historic home on Smith Island w/ dock!
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
9.8 out of 10, Exceptional, 120 reviews
"We all enjoyed our stay at Down by the Bay. The house comfortably accommodated all 15 of us and we made good use of the kayaks and paddle boards provided. The golf cart to the dock was a really nice touch and made up for the fact that there is not direct water access to the swimming area from the house. The sunsets from the porch were incredible."
The price is €902
includes taxes & fees
8 Jul - 9 Jul
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
10.0 out of 10, Exceptional, 13 reviews
"Wonderful relaxing three days. Marykim terrific in assisting us"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
10.0 out of 10, Exceptional, 42 reviews
"My husband and I loved our visit to Sunrise Cottage! Everything was perfect and we can't wait to return."
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
Stylish Condo with a Great View
9.4 out of 10, Exceptional, 6 reviews
"Perfect location and beautiful sunsets from the deck. It would be best advised if you notify the tenants if there will be an event held down stairs. The apartment is upstairs over a private club, Saturday night had an event downstairs that had music going until the early morning. Couldn’t sleep and ruined my last night of other wise a perfect stay!"
The price is €386
includes taxes & fees
15 Jul - 16 Jul
Stylish Condo with a Great View
Come, sit back and relax at the "Catch of the Bay"
10.0 out of 10, Exceptional, 4 reviews
"Our stay at Catch of the Bay was wonderful. House is immaculate, cozy, and just minutes away from the beach and restaurants. Janell has really outdone herself with thinking of everything to make our stay just perfect and never made me feel as if I was a bother when I had questions. If we visit this area again, we will definitely look to see if this location is available. God Bless!"
Come, sit back and relax at the "Catch of the Bay"
Home in the Heart of Salisbury 3BR 4 Beds Sleeps 8 Blocks from SU and Downtown
10.0 out of 10, Exceptional, 2 reviews
"The house was clean and nicely updated, located in a quiet neighborhood near the University. What really impressed us was the hospitality. The host provided everything you could possibly need for a comfortable stay. Close to downtown and plenty of options for a morning run or walk."
Home in the Heart of Salisbury 3BR 4 Beds Sleeps 8 Blocks from SU and Downtown
The Blackwater refuge country house on a quiet 12 acres
10.0 out of 10, Exceptional, 4 reviews
"Property owner was great. He text to answer a question and proceeded to give advice on the fishing we were there to do."
The Blackwater refuge country house on a quiet 12 acres
The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views
10.0 out of 10, Exceptional, 3 reviews
"Lovely home - clean and quiet - fit the bill for a quick trip to the Salisbury area. As advertised it is kind of remote and there is not too much around (eg food) that doesn’t require a 10-15 minute car ride."
The price is €488
includes taxes & fees
8 Jul - 9 Jul
The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views
Cottage on the Bay
9.6 out of 10, Exceptional, 5 reviews
"Great view, very secluded. House was very spacious and well supplied. Host was very accommodating. Would definitely stay again."
Cottage on the Bay
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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.

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

Quaint Island Getaway
10.0 out of 10, Exceptional, 11 reviews
"This is a charming place, full of really nice interior touches. The location gives you access to some great marshland so you are treated to a daily dose of great bird sightings, including ospreys, red-winged blackbirds, herons and others. The house has everything you need. The only advice I would give - to remind guests to clean off the grill when they are done using it. We had to clean it thoroughly as it had obviously not been cleaned in awhile. I suggest you add that to the short list of...
Quaint Island Getaway
Hampton Inn & Suites Salisbury/Fruitland
2.5 star property
9.2 out of 10, Wonderful, 1,000 reviews
"Very clean and friendly staff "
The price is €131
includes taxes & fees
4 Aug - 5 Aug
Hampton Inn & Suites Salisbury/Fruitland
Holiday Inn Express Pocomoke, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, 695 reviews
"Came to stay at the hotel for my Bday. Didn’t get to see any horses 😔.!but that’s ok. The room was nice, the staff was friendly. They were in the middle of a remodel, and kept having problems with the key cards working right. This is the first hotel I’ve ever stayed at where the key cards were not touch to open. Hopefully if/when I stay here again, that they go to a touch to open lock system. But other than the key card issue, my stay was pleasant. On a sidenote, I do wish they had waffles as...
The price is €168
includes taxes & fees
9 Jul - 10 Jul
Holiday Inn Express Pocomoke, an IHG Hotel
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.

Everything you need to know about Deal Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Deal Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Deal Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Deal Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Deal Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Deal Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Deal Island holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Deal Island rentals

At Expedia, we put the best Deal Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Deal Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Deal Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Deal Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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?

Enjoy the area's cultural attractions such as J. Millard Tawes Museum, or get outdoors into nature at a spot like Shark Fin Shoal. In the wider area, you’ll find Lower Hooper Island and Smith Island.

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.

Recent reviews of Deal Island properties
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