Discover a selection of 16 vacation rentals in Deal Island, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $82 per night, and houses and cottages are popular options for a stay in Deal Island. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Deal Island
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Destination guide

Tranquil Deal Island will entice you

The island views and surrounding scenery provide a peaceful ambiance to your vacation home in Deal Island. Well-liked for its seafood restaurants, fishing and bars, this city is both relaxing and walkable. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Things to do

Activities and attractions in Deal Island

Are you looking for attractions to see in the area? Venture out of your cozy vacation rental and check out everything that Deal Island has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Bordeleau Winery (14.8 mi / 23.8 km)
  • Great Hope Golf Course (13.3 mi / 21.3 km)
Natural features

Exploring the natural landscape of Deal Island

Travelers enjoy Deal Island for its island views and sunsets. Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Deal Island is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Lower Hooper Island (11.8 mi / 18.9 km)
  • Smith Island (12.9 mi / 20.8 km)
  • Blackwater National Wildlife Refuge (20.7 mi / 33.3 km)
  • Middle Hooper Island (15.3 mi / 24.6 km)
  • Shark Fin Shoal (4.3 mi / 6.9 km)
How to get there

How to get to and around Deal Island

Fly into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), the closest airport, located 26.6 mi (42.8 km) from the city center.

What are the top vacation rentals in Deal Island?

Deluxe villas, tranquil houseboats and rustic cottages — everyone's ideal getaway is different. Whatever your style, you're sure to find something that tempts you among these top vacation rentals in Deal Island:

  • "Clean Comfortable Condo": If you're searching for someplace in Las Vegas with 1 bedroom where you'll feel right at home, this escape is calling your name. Amenities include a stereo and winery tours.
  • "Waterfront Cottage": Stay at this escape in Chance and take advantage of heating, high-speed internet services and more. It has 1 bedroom to accommodate your favorite people.

For even more great options, use the search bar at the top of the page to find the perfect Deal Island vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in Deal Island?

While extended vacations to new places are epic, there's something lovely about heading off on a weekend getaway. These rental properties in Deal Island are perfect for just that:

  • "Chesapeake Bay Waterfront Home" - This retreat in Somerset County offers amenities that'll make your visit nice and comfortable, such as a hair dryer and a kitchen. Its wonderful location also makes it a good base to do some exploring.
  • "Deal Island Bay Cottage" - This is another option offering all the things that make up a relaxing getaway. Expect towels and a kitchen at this Chance rental.

Can I find studio apartments for rent in Deal Island?

If you're after something a little more personal than a cookie-cutter hotel room, you'll like our studio apartments in Deal Island. Cook up a meal in your kitchen, snooze on the lounge and feel completely at home. Here are some of our comfiest studios:

  • "Clean Comfortable Condo" in Las Vegas packs a bunch of handy features into its single space, including a bicycle and outdoor furniture.
  • Start your day with a cup of coffee and fried-up eggs and bacon at "Waterfront Cottage". This Chance escape has everything you need to make your stay comfy, including a kitchen and a fridge.

Can I find short term rentals in Deal Island?

Book yourself a cheap and cheerful cabin or live life large in a luxury condo. Vrbo has loads of short-term rentals for your vacation in Deal Island. Check out these properties for inspiration:

  • "Chesapeake Bay Waterfront Home" in Somerset County is a perfect place for a short-term stay. It's only a stone's throw from the center of town, so you can visit all the top sights without having to travel too far.
  • "Deal Island Bay Cottage" also rolls out the welcome mat for short-term guests. Spend a couple of leisurely days at this option in Chance and find out why it's a hit with many travelers.

What are the best romantic weekend getaways in Deal Island?

A romantic weekend getaway in Deal Island is sure to fan the flames of passion. Light some pretty candles, grab your honey by the hand and get set to send sparks flying at one of these retreats:

  • Enjoy some "us time" at "Clean Comfortable Condo". This Las Vegas stay is ideal for romance, offering amenities like massage services and a nearby bay to help set the mood.
  • Alternatively, treat you and your love to an amorous weekend away at "Waterfront Cottage". Located in Chance, it offers a nearby bay, a restaurant dining guide and more.

What are the best large family vacation rentals in Deal Island?

There's nothing like a vacation to bring your family together, but first, you need to find a space where the magic can happen. These large family vacation rentals in Deal Island come with tons of room to stretch out and relax with your loved ones:

  • If you need an escape that'll sleep up to 8 guests, try "Chesapeake Bay Waterfront Home" in Somerset County. With 3 bedrooms, a toaster and towels, your next family adventure will be a winner.
  • Alternatively, lock in your family escape at "The Relax - Inn Deal Island With Kayaks And Canoe". This The South property has 4 bedrooms and can accommodate up to 8 guests. Take advantage of a living room and coffee and tea making facilities throughout your stay.

Can I find family cabin rentals in Deal Island?

If you're dreaming of a trip with the fam, book one of these cabin rentals in Deal Island and give the kids a vacation they'll cherish forever:

  • "Boulder Ridge Cabin - A Private Chalet In The Woods" - Escape the 9-to-5 of city living at this Friendsville retreat which offers towels and a stereo.
  • "Fw Drei - Landhaus Ostseeblick" – This option in Crystal City is also a big hit with families. Conveniences here include nearby birdwatching activities and a dishwasher.

For more options, use the search bar at the top of the page and adjust the filters to find the Deal Island vacation rental that's perfect for your needs.

Are there one-bedroom vacation rentals in Deal Island?

Vrbo has an impressive selection of one-bedroom vacation rentals in Deal Island. Whether you're searching for an upmarket apartment or a simple cabin, we'll help you find a perfect one-bedroom property. Here are a few to try on for size:

  • Go by yourself or take a few pals with you to "Gorgeous Direct Ocean Front Condo Overlooking Pool And Beach" in North Ocean City. When you're not checking out nearby attractions, make use of a kitchen and a water view.
  • Or, unpack your suitcase and make yourself at home at "Fabulous, Historic One Bedroom Capitol Hill Apartment With Off Street Parking". A swimming pool and a kitchen are just some of the amenities you'll have at your disposal at this property in Capitol Hill.

What are the best three-bedroom vacation rentals in Deal Island?

There's nothing better than a trip away with family or friends, but the tough part can be finding a place that'll fit everybody in. The great news? There are loads of three-bedroom rentals in Deal Island waiting for you, starting with these:

  • After a long day of seeing the sights, you and your companions can relax at "Chesapeake Bay Waterfront Home". Situated in Somerset County, this escape comes with a nearby waterfront, a kitchen and all the room you want.
  • Another three-bedroom option that'll appeal to your gang is "Deal Island Bay Cottage". This Chance property features a firepit, a kitchen and more.

Are there vacation rentals with fire pits in Deal Island?

There's something so cozy about closing your eyes and listening to a roaring fire. If the idea of roasting marshmallows under the starlight appeals to you, take a look at these wonderful getaways in Deal Island:

  • Stay at "Deal Island Bay Cottage" and you'll be able to kick back and relax in front of a crackling fire every night. This popular property in Chance comes with a firepit and a kitchen, as well as a lovely fire pit.
  • Or, get comfy at "The Relax - Inn Deal Island With Kayaks And Canoe", which also features an outdoor fire pit. Other amenities at this popular escape in The South include a kitchen and a garden.