
Find Hotels with a Pool in St. Michaels, MD from CA $129
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Sep 18 - Sep 20Our top choices for St. Michaels hotels with a pool




1. St Michaels Inn
St Michaels InnSt. Michaels
- Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
CA $118
CA $129 total
includes taxes & fees
Oct 7 - Oct 8




2. George Brooks House B&B
George Brooks House B&BSt. Michaels
- Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
CA $293
CA $322 total
includes taxes & fees
Sep 7 - Sep 8




3. Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
- Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
CA $834
CA $918 total
includes taxes & fees
Sep 29 - Sep 30




4. Knapps Narrows Marina & Inn
Knapps Narrows Marina & InnSherwood
- Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
CA $208
CA $228 total
includes taxes & fees
Sep 7 - Sep 8




5. The Tilghman Island Inn
The Tilghman Island InnTilghman
- Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
CA $284
CA $312 total
includes taxes & fees
Sep 16 - Sep 17




6. Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & SuitesEaston
- Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
CA $179
CA $196 total
includes taxes & fees
Sep 27 - Sep 28




7. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
CA $165
CA $183 total
includes taxes & fees
Oct 5 - Oct 6




8. Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott EastonEaston
- Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.
CA $187
CA $206 total
includes taxes & fees
Sep 13 - Sep 14
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Top St. Michaels Hotel Reviews
Hyatt Regency Chesapeake Bay
10/10 Excellent
"Would definitely return in the near future. My family had fun."
Sonesta ES Suites Annapolis
8/10 Good
"Ver nice older hotel but well maintained. Spacious rooms and good breakfast. My only complaint is that you can tell they also keep long term tenants as there were cats roaming around (which didn’t bother me but might others) and bikes/trash outside some of the rooms and plants in windows. A normal nightly rental hotel would not allow this id think so it made the atmosphere seem a lil run down even if the room was decent."
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
"Rooms kept very clean and comfortable. Staff excellent, extremely friendly and helpful. Food very good and good portions."
George Brooks House B&B
8/10 Good
"We enjoyed our stay but found a few things that could have been better. Our host (Will) was not present the first day and most likely did not know the coffee and tea bar had sour milk and no sugar. I took it upon myself to rummage around and find these things but I would have liked it better if they were there. Also, we had a scrap of toilet paper in our room and no refills so I had to find that as well. Small things but not a good first impression. Otherwise, the room was very comfortable, the pool was great and the breakfast was delicious."
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