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Compare 40 Vacation Homes in Deal Island with updated reviews, rates, and availability.

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 SAR 338
SAR 749 total
includes taxes & fees
25 Dec - 26 Dec
Cottage near the Bay

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!

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

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

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (9)
"Listing and photos accurately describe accommodations. We were comfortable and satisfied. A nice rural location for perusing outdoor activities - fishing, hunting, boating, paddling, birdwatching. Good parking for a boat trailer. "
The Blackwater refuge country house on a quiet 12 acres

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!

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!

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

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!

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!

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"

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"

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

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

BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!

10.0 out of 10, Exceptional, (62)
"A wonderful long weekend getaway on Hoopers Island--close to the bay and to the attractions of the island. Laura is a great host who ensured we had everything we needed for our stay--a roomy house with a great screened in gazebo and plenty of activities for our elementary school aged kids. Highly recommend it!"
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!

Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

10.0 out of 10, Exceptional, (1)
"As many reviewers say, Smith Island is not a hot spot teaming with places to go. We knew this when booking. We brought our cameras, our water colors to paint, books, knitting, cards.... we had a WONDERFUL time. The cottage was beautiful and had everything we needed. The host even supplied us with board games and bug spray. We walked the length of the island several times and spent most mornings with our binoculars and cameras birding. If you want to relax and can entertain yourself it is a...
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

Salisbury Hideaway

10.0 out of 10, Exceptional, (15)
"We appreciated how clean the house was! It was a perfect place to come back to after a full day of exploring Maryland Definitely would stay there again."
The price is SAR 492
SAR 1,275 total
includes taxes & fees
7 Jan - 8 January 2025
Salisbury Hideaway

Salisbury Cottage

10.0 out of 10, Exceptional, (23)
"We were in town for our daughter’s graduation from Salisbury University. The house was very cozy and perfectly situated close to the school. It was clean and very well maintained and decorated. Our only complaint is that we weren’t able to stay longer. If you are visiting the Salisbury area I highly recommend booking this house."
The price is SAR 492
SAR 1,271 total
includes taxes & fees
5 Jan - 6 January 2025
Salisbury Cottage

Quiet Townhome with Full Kitchen, Private Washer/Dryer, WiFi & Central AC

9.0 out of 10, Wonderful, (8)
"Property was well maintained and accessible. Our only complaint was lack of necessary supplies. Information noted necessary items supplied but would have to restock on our own should we run out. However, there was no hand soap in 1/2 bath downstairs, no dish detergent to wash dishes and only a small part of paper towel roll. Would also suggest at least one box of tissues somewhere in unit. Otherwise we enjoyed our stay! "
Quiet Townhome with Full Kitchen, Private Washer/Dryer, WiFi & Central AC

Single family home with screened porch.

10.0 out of 10, Exceptional, (10)
"The house was very nicely done and extremely well stocked and the host was very friendly and super easy to deal with. We especially like the location for sunrise walks with the dogs and easy access to the national parks. "
Single family home with screened porch.
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.
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Other property types in Deal Island

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is SAR 432
SAR 860 total
includes taxes & fees
7 Jan - 8 January 2025
Deal Island Bay Cottage

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

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
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.