Deal Island Vacation Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Deal Island

Deal Island Bay Cottage
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is CA $165
CA $326 total
includes taxes & fees
Jan 21 - Jan 22, 2025
Deal Island Bay Cottage
Quaint Island Getaway
Beach nearby, sun loungers

Quaint Island Getaway

10.0 out of 10, Exceptional, (13)
"Staying at the Quaint Island Getaway is always a pleasure! Sarah is an accessible host, the property is cozy and clean. My party loved the new firepit."
Quaint Island Getaway
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Dining

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our stay was perfect. The home was quite lovely and equipped with all amenities. The location was very nice. The bay was only a 2 minute walk at the end of the street. Highly recommend."
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Waterfront Maryland Retreat w/ Dock & Bay View!
Beach

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (6)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!
Cottage near the Bay
Dining

Cottage near the Bay

8.8 out of 10, Excellent, (28)
"Our stay at the Cottage near the Bay was fantastic and exactly what my family needed. The host went above and beyond to communicate with us and make our stay excellent. The cottage was very clean, cozy, and a welcome escape. When we come back to Crisfield we won't be staying anywhere else, as long as it isn't already booked!"
The price is CA $129
CA $286 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Cottage near the Bay
Waterfront Cottage in Beautiful Hoopers Island
Property grounds

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (65)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island
The Schultz Estate
Outdoor dining

The Schultz Estate

8.8 out of 10, Excellent, (14)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate
Sunset Retreat on the Nanticoke
Miscellaneous

Sunset Retreat on the Nanticoke

10.0 out of 10, Exceptional, (11)
"This property was exactly what we were looking for our family vacation. Location on the water, the amenities were above and beyond, comfortable beds, and land as far as you could see. The fishing and crabbing was exceptional for all ages. The kids loved crabbing, new to us, caught some turtles as well, all released back. Paddle boarding and kayaking on morning water (like glass), was on the daily. There is a perfect fire pit area to enjoy. The large open concept home is perfect for the...
Sunset Retreat on the Nanticoke
Waterfront Marion Station Retreat w/ Private Dock!
Fridge, microwave, stovetop, dishwasher

Waterfront Marion Station Retreat w/ Private Dock!

8.6 out of 10, Excellent, (4)
"Home offers breathtaking views of the bay. Plenty of space for two families with children. Would love to come back!"
Waterfront Marion Station Retreat w/ Private Dock!
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, (8)
"Very clean. Nice layout. Lots of extras. Good neighborhood. Highly recommend it!"
Home in the Heart of Salisbury 3BR 4 Beds Sleeps 8 Blocks from SU and Downtown
Beautiful Bayfront with Sanctuary Private Beach
Property grounds

Beautiful Bayfront with Sanctuary Private Beach

9.0 out of 10, Wonderful, (17)
"The property is beautiful and it was so nice to be so close to the water. Sunset view and fire pit out back were fun bonuses. Everything went smoothly and as expected. We enjoyed our stay, thank you!"
Beautiful Bayfront with Sanctuary Private Beach
Historic Hoopersville Getaway on Chesapeake Bay!
Fridge, microwave, stovetop, dishwasher

Historic Hoopersville Getaway on Chesapeake Bay!

9.6 out of 10, Exceptional, (10)
"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 on the Bay
Miscellaneous

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay
Spectacular Waterfront on the Pocomoke River!
Aerial view

Spectacular Waterfront on the Pocomoke River!

9.8 out of 10, Exceptional, (6)
"Such a lovely home on the perfect piece of property. We loved the porch and the firepit. Enough room for 8 people and a dog!"
Spectacular Waterfront on the Pocomoke River!
Dog-Friendly Westover Cottage w/ River Access!
Fridge, microwave, stovetop, dishwasher

Dog-Friendly Westover Cottage w/ River Access!

10.0 out of 10, Exceptional, (6)
"As a mom of two , one with Tourette’s and comorbidies that go with it, relaxing getaways are few and far between. This was just what the doctor ordered. Kayaking, fishing, nature walks!! "
Dog-Friendly Westover Cottage w/ River Access!
Waterfront 3 bedroom condo. Fall and oysters are here!
Outdoor pool

Waterfront 3 bedroom condo. Fall and oysters are here!

10.0 out of 10, Exceptional, (37)
"The unit is well maintained, with ample supplies for cooking . Jetted tub was great, and beds were comfortable. The view was fantastic, and we spent much of our time slowing down from our hectic lives just looking out at the water and at the birds (there was a bald eagle as well!). Love this place"
Waterfront 3 bedroom condo. Fall and oysters are here!
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Miscellaneous

Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (36)
"The location was perfect, our host was extremely responsive and helpful. Chris gave us tips and set us up with the ferry Captain. Even though the large restaurant was closed there are 2 chefs that prepare wonderful meals! The srore/museum was ooen go meet the sweet manager! Thank you Chris for a wonderful family vacation!"
Historic home on Smith Island w/ dock!
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, (5)
"This was a great place to stay and I highly recommend it to anyone. We were really impressed with all the "extras" that were included. We didn't need to go out any buy anything unexpected."
Come, sit back and relax at the "Catch of the Bay"
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

9.8 out of 10, Exceptional, (6)
"We spent one evening at this quaint cottage. The setting is rustic; yet calm and quiet. The house has been completely updated, and many thoughtful extra items were included. The beds were comfortable. The listing said that there were two bathrooms. There was only one. Of special interest was a garage with several nice kayaks for our use."
The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views
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.
Don't see what you're looking for?
See all available properties in Deal Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Deal Island Bay Cottage
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is CA $165
CA $326 total
includes taxes & fees
Jan 21 - Jan 22, 2025
Deal Island Bay Cottage
Quaint Island Getaway
Beach nearby, sun loungers

Quaint Island Getaway

10.0 out of 10, Exceptional, (13)
"Staying at the Quaint Island Getaway is always a pleasure! Sarah is an accessible host, the property is cozy and clean. My party loved the new firepit."
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, (1000)
"Good location for event i was attending, local stores and restaurants within walking distance. Lobby nicely appointed with holiday decorations. Beds were very comfotable. My room was outdated with old chipped furniture. There was a wait for clean towels. Not enough towels for 4 people staying in room. Ice machine not working on 3rd flood. "
The price is CA $161
CA $180 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Hampton Inn & Suites Salisbury/Fruitland
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.

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 6 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.