Deal Island Holiday Rentals

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Holiday 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 NZ$640
includes taxes & fees
9 Jun - 10 Jun
Beautiful Bayfront with Sanctuary Private Beach
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Cottage near the Bay
Private kitchen
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 NZ$322
includes taxes & fees
5 Jun - 6 Jun
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
10.0 out of 10, Exceptional, (4)
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
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
8.8 out of 10, Excellent, (3)
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 NZ$1,642
includes taxes & fees
7 Jun - 8 Jun
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 NZ$763
includes taxes & fees
5 Jun - 6 Jun
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)
"The property was amazing and any minor issue we had. They were right there to fix it. The island was welcoming, as well as just the right amount of quiet and slow down that we were looking for. I recommend anybody needing to detach disconnect to enjoy property for a couple of days or even longer. The hospitality was amazing. We will be back."
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
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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)
"Excellent "
The price is NZ$215
includes taxes & fees
10 Jun - 11 Jun
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 NZ$273
includes taxes & fees
20 Jun - 21 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Deal Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Deal Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Deal Island. Seeing all the best attractions is bound to make you fall in love with Deal Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Deal Island short-term rentals, that won’t be hard to do.

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 3 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
Expedia verified reviews

Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly

Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly

5/5 Excellent
Great for a Family Vacation!
"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 unless you go back down the driveway & up the road to another driveway, probably about a 10 minute walk with the kids. The road isn’t too busy but there isn’t a sidewalk, so not ideal for little ones. I think this is a new dynamic, since the house next door recently sold & the new neighbors are unwilling to share use of their walkway across their yard. Neighbors on the other side have a small beach that is pictured in the listing, but that is now also fenced off & marked as private property. Highly recommend bringing a small pool if you have little ones!"
A verified traveller stayed at Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
Posted 4 days ago
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly