Deal Island Vacation Rentals

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Vacation Rentals in Deal Island

Quaint Island Getaway
Beach nearby, sun loungers
Quaint Island Getaway
10.0 out of 10, Exceptional, (11)
"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
Simply the best...Beautiful condo overlooking the Chesapeake bay.
Smart TV, fireplace
Simply the best...Beautiful condo overlooking the Chesapeake bay.
10.0 out of 10, Exceptional, (102)
"Beautiful accommodation, beautiful hosts, beautiful sunsets, and a beautiful time."
Simply the best...Beautiful condo overlooking the Chesapeake bay.
Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (55)
"Very clean small cottage in a beautiful spot. I was able to swim off the dock. There was plenty of outdoor space with comfortable Adirondack chairs. Very quiet at night and the beds were comfortable. Our host was most kind."
Waterfront Cottage in Beautiful Hoopers Island
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Cottage near the Bay
Fridge, microwave, oven, stovetop
Cottage near the Bay
8.8 out of 10, Excellent, (15)
"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 CA $123
CA $273 total
includes taxes & fees
Jul 18 - Jul 19
Cottage near the Bay
Beautiful Bayfront with Sanctuary Private Beach
Outdoor dining
Beautiful Bayfront with Sanctuary Private Beach
8.8 out of 10, Excellent, (13)
"Nice, relaxing stay!"
The price is CA $369
CA $594 total
includes taxes & fees
Jul 13 - Jul 14
Beautiful Bayfront with Sanctuary Private Beach
The Schultz Estate
Outdoor dining
The Schultz Estate
9.8 out of 10, Exceptional, (6)
"This property was great for our extended family of 8 and could have comfortably accommodated more. The old charm of the house was enjoyed by all. Great kitchen, functioning bbq, large dining room table and a fire pit for us all to enjoy. The sunset was beautiful as we sat outside in the evening. Wifi is available but it is limited so some online activities may not always be possible - but not a bad thing when you are spending time with family."
The Schultz Estate
Waterfront 3 bedroom condo. Summer has arrived, pool is open!
Outdoor pool
Waterfront 3 bedroom condo. Summer has arrived, pool is open!
10.0 out of 10, Exceptional, (22)
"Very relaxing"
Waterfront 3 bedroom condo. Summer has arrived, pool is open!
Historic home on Smith Island w/ dock!
Beach
Historic home on Smith Island w/ dock!
9.6 out of 10, Exceptional, (31)
"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!
Historic Hoopersville Getaway on Chesapeake Bay!
Fridge, microwave, stovetop, dishwasher
Historic Hoopersville Getaway on Chesapeake Bay!
9.6 out of 10, Exceptional, (9)
"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!
BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!
Property grounds
BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!
10.0 out of 10, Exceptional, (4)
"Great time in a very updated & comfortable home."
BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
View from property
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
10.0 out of 10, Exceptional, (2)
"Easy access, mind blowing decor, most well-equipped kitchen. Every detail was a delight! Just lovely. And the sunsets, OMG! Instructions were clear and simple. Kelly was attentive and checked up on us. Just wonderful all around."
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
Riverfront Cabin Getaway at The Brackish - Pet Friendly!
Interior
Riverfront Cabin Getaway at The Brackish - Pet Friendly!
2.0 star property
8.0 out of 10, Very good, (1)
"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!
The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views
Fridge, microwave, oven, dishwasher
The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views
10.0 out of 10, Exceptional, (2)
"Nice house. Great location for fishing plenty of room for a boat. Quiet area."
The price is CA $304
CA $707 total
includes taxes & fees
Jun 29 - Jun 30
The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
Pool
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
9.8 out of 10, Exceptional, (117)
"Overall the place was great, clean, and comfortable for 8 adults & 3 kids. There were 4 kayaks & 2 bikes we used & a small swing set that was perfect for the kids (all under 5). Kitchen and grill worked well for what we needed & the location next to Old Saltys was great to listen to music in the back yard! One important thing to note is that it isn’t really waterfront - more water adjacent. You have a clear view to the bay, but there is not any beach area for kids & you can’t access the dock...
The price is CA $850
CA $1,504 total
includes taxes & fees
Jul 9 - Jul 10
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
Exterior
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
10.0 out of 10, Exceptional, (42)
"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.
Home in the Heart of Salisbury 3BR 4 Beds Sleeps 8 Blocks from SU and Downtown
Smart TV, fireplace
Home in the Heart of Salisbury 3BR 4 Beds Sleeps 8 Blocks from SU and Downtown
10.0 out of 10, Exceptional, (2)
"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
Salisbury Hideaway
Property grounds
Salisbury Hideaway
10.0 out of 10, Exceptional, (10)
"The Salisbury cottage was wonderful. Close to campus and on a quiet street so my children could ride their bikes safely."
The price is CA $182
CA $474 total
includes taxes & fees
Jun 30 - Jul 1
Salisbury Hideaway
Come, sit back and relax at the "Catch of the Bay"
Terrace/patio
Come, sit back and relax at the "Catch of the Bay"
10.0 out of 10, Exceptional, (3)
"It was very good, very clean and cozy. I would recommend the place for sure."
Come, sit back and relax at the "Catch of the Bay"
Dog-Friendly Westover Cottage w/ River Access!
Fridge, microwave, stovetop, dishwasher
Dog-Friendly Westover Cottage w/ River Access!
Dog-Friendly Westover Cottage w/ River Access!
Cottage on the Bay
Outdoor dining
Cottage on the Bay
9.6 out of 10, Exceptional, (5)
"Great view, very secluded. House was very spacious and well supplied. Host was very accommodating. Would definitely stay again."
Cottage on the Bay
Don't see what you're looking for?
See all available properties in Deal Island
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
Beach nearby, sun loungers
Quaint Island Getaway
10.0 out of 10, Exceptional, (11)
"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
Room, 2 Queen Beds, Accessible, Non Smoking
Hampton Inn & Suites Salisbury/Fruitland
2.5 star property
9.2 out of 10, Wonderful, (1001)
"Safe area and very friendly staff and excellent breakfast!!"
The price is CA $174
CA $194 total
includes taxes & fees
Jul 15 - Jul 16
Hampton Inn & Suites Salisbury/Fruitland
Holiday Inn Express Pocomoke, an IHG Hotel
Indoor pool
Holiday Inn Express Pocomoke, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (693)
"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 CA $259
CA $288 total
includes taxes & fees
Jun 30 - Jul 1
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Deal Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Deal Island vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Deal Island vacation 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 vacation 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 vacation.

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 vacation rental in Deal Island?

Yes, we offer vacation rentals near well known sights in Deal Island, or you can go with a more secluded option if you'd like a relaxing place to 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 vacation rentals that Deal Island has to offer?

Quaint Island Getaway: This highly rated vacation home rental in Deal Island is located near the beach and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Deal Island?

With 4 Expedia vacation rentals, you're sure 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 larger area, you’ll find Smith Island and Somers Cove Marina.

What’s a vacation rental in Deal Island like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Deal Island. Vacation rentals feature extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.

Recent reviews of Deal Island properties
Expedia verified reviews

Holiday Inn Express Pocomoke, an IHG Hotel

Holiday Inn Express Pocomoke, an IHG Hotel

5/5 Excellent
Bday vacation stay.
"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 an option for for breakfast. But that’s just me."
A verified traveller stayed at Holiday Inn Express Pocomoke, an IHG Hotel
Posted 2 days ago
Holiday Inn Express Pocomoke, an IHG Hotel