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
Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
Beautiful Bayfront with Sanctuary Private Beach
Outdoor dining
Beautiful Bayfront with Sanctuary Private Beach
9.2 out of 10, Wonderful, (10)
"House was exactly as advertised and expected. Would stay agian for sure"
The price is $239
$396 total
includes taxes & fees
Jun 9 - Jun 10
Beautiful Bayfront with Sanctuary Private Beach
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Cottage near the Bay
Private kitchen | Fridge, microwave, oven, stovetop
Cottage near the Bay
9.0 out of 10, Wonderful, (13)
"Come stay at this wonderful house in lovely Crisfield Maryland. You won't be sorry. The host is fantastic and gets back to you quickly if you have questions. Thank you for everything."
The price is $90
$198 total
includes taxes & fees
Jun 6 - Jun 7
Cottage near the Bay
Waterfront 3 bedroom condo. Spring is here!
Outdoor pool
Waterfront 3 bedroom condo. Spring is here!
10.0 out of 10, Exceptional, (20)
"Very relaxing time. The condo was beautiful"
Waterfront 3 bedroom condo. Spring is here!
The Schultz Estate
Outdoor dining
The Schultz Estate
9.6 out of 10, Exceptional, (5)
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
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"
Pet-Friendly Quantico Home w/ River Views!
Property grounds
Pet-Friendly Quantico Home w/ River Views!
10.0 out of 10, Exceptional, (2)
"Beautifully decorated and clean spacious waterfront house with plenty of amenities. Plenty of rooms and outdoor areas to enjoy."
Pet-Friendly Quantico Home w/ River Views!
Quiet Townhome with Full Kitchen, Private Washer/Dryer, WiFi & Central AC
TV
Quiet Townhome with Full Kitchen, Private Washer/Dryer, WiFi & Central AC
8.6 out of 10, Excellent, (4)
Quiet Townhome with Full Kitchen, Private Washer/Dryer, WiFi & Central AC
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, (3)
"Excellent"
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!
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
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 $550
$1,009 total
includes taxes & fees
Jun 7 - Jun 8
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.
Historic home on Smith Island w/ dock!
Beach
Historic home on Smith Island w/ dock!
9.4 out of 10, Exceptional, (30)
"This was a perfect spot for out three-generation getaway. Property was a perfect fit for us and the new deck with screened-in porch is a great addition to this property. Well stocked kitchen made meal prep a breeze, and the gas grill came in very handy. Comfy furniture and a great dining room table perfect to game night."
Historic home on Smith Island w/ dock!
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
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, (101)
"The condo was perfect. Checkin was easy, was as described and the view was amazing. Would recommend to anyone looking for a relaxing getaway"
Simply the best...Beautiful condo overlooking the Chesapeake bay.
Victorian Get Away
Private kitchen
Victorian Get Away
Victorian Get Away
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 $181
$464 total
includes taxes & fees
Jun 6 - Jun 7
The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Exterior
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
10.0 out of 10, Exceptional, (12)
"Kim and Mickey made us feel very welcomed and the waterfront home was immaculate with a well equipped kitchen and beautiful flowers! We had a wonderful visit! Thanks again. Julie"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
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 | In-room safe, desk, blackout drapes, iron/ironing board
Hampton Inn & Suites Salisbury/Fruitland
2.5 star property
9.2 out of 10, Wonderful, (1001)
"Excellent "
The price is $127
$142 total
includes taxes & fees
Jun 16 - Jun 17
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, (684)
"Friendly Staff"
The price is $168
$186 total
includes taxes & fees
Jun 20 - Jun 21
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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Deal Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 3 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 Lower Hooper Island and Smith Island.

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

Econo Lodge Princess Anne

Econo Lodge Princess Anne

5/5 Excellent
"I enjoyed my stay here. I arrived @ 10:30 am and check in was 2pm so happy that they let me check in @ 11am. Drove from new york for the crab and cruise event. My room was clean towels smelled great. I absolutely enjoyed my stay. Thank u guys for being so nice 💓 "
A verified traveler stayed at Econo Lodge Princess Anne
Posted 15 hours ago
Econo Lodge Princess Anne