Find Hotels with a Pool in Smith Island, MD

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Check availability on Smith Island Hotels with a Pool

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Dec 6 - Dec 7
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Dec 7 - Dec 8
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Top Smith Island Hotels with a Pool

House, Ensuite, Harbor View (Kingsbay Bayhouse) | Exterior
Kingsbay Mansion & Vacation Houses

Kingsbay Mansion & Vacation Houses

3.5 star property
Marion Station
9.8 out of 10, Exceptional, (28)
"An overall excellent place to stay, relax and rest "
United States
Tracy
The price is ￥64,695
￥71,812 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Kingsbay Mansion & Vacation Houses
Outdoor pool
Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

2.0 star property
Crisfield
8.6 out of 10, Excellent, (124)
"Place was perfect for our stop on the way to the Outer Banks. Room was clean, beds were comfy and kids enjoyed the pool "
United States
Jeremy
The price is ￥13,184
￥14,898 total
includes taxes & fees
Dec 19 - Dec 20
Rodeway Inn at Somers Cove Marina
6 bedrooms, desk, iron/ironing board, free WiFi
Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!

Reedville
8.0 out of 10, Very Good, (1)
"We had a great time. The host was very welcoming and helpful. Hope to go back again."
United States
holly u.
The price is ￥76,376
￥160,285 total
includes taxes & fees
Dec 7 - Dec 8
Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
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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Top Smith Island Hotel Reviews

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Frequently asked questions

What are some accommodations with pools in Smith Island?
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart: Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Historic home on Smith Island w/ dock!: Features kitchens, a pool, and televisions. Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island: Features complimentary wireless internet access, a pool, and kitchens.
What is there to see and do in Smith Island?
The picturesque setting of Smith Island and Chesapeake Bay showcase the area's natural beauty. Discover sights such as Horse Hammock and Tylerton County Dock during your stay.
When is the best time to book a hotel with a pool in Smith Island?
You may want to consider a place to stay that has an outdoor pool if you plan to visit Smith Island in the warmest months of July, August, or June when the average temp is 76°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 42°F.