Find Hotels with a Pool in St. Michaels, MD

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Top St. Michaels Hotels with a Pool

St Michaels Inn

2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1007)
"clean and comfy, friendly staff"
United States
Tamara
The price is SAR 388
SAR 427 total
includes taxes & fees
23 Dec - 24 Dec
St Michaels Inn

George Brooks House B&B

3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is SAR 638
SAR 702 total
includes taxes & fees
1 Jan - 2 January 2026
George Brooks House B&B

Inn at Perry Cabin

5.0 star property
St. Michaels
9.6 out of 10, Exceptional, (370)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is SAR 1,353
SAR 1,637 total
includes taxes & fees
4 Dec - 5 Dec
Inn at Perry Cabin

Parsonage Inn

3.5 star property
St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is SAR 750
SAR 825 total
includes taxes & fees
1 Jan - 2 January 2026
Parsonage Inn

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1003)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is SAR 391
SAR 509 total
includes taxes & fees
4 Dec - 5 Dec
Rod 'N' Reel Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (127)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is SAR 405
SAR 578 total
includes taxes & fees
8 Dec - 9 Dec
Kent Island Resort

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (928)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is SAR 297
SAR 330 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
9.4 out of 10, Exceptional, (359)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is SAR 450
SAR 495 total
includes taxes & fees
7 Dec - 8 Dec
Knapps Narrows Marina & Inn

Wylder Tilghman Island

2.0 star property
Tilghman
8.8 out of 10, Excellent, (89)
"Very relaxing stay."
United States
Anne
The price is SAR 450
SAR 661 total
includes taxes & fees
1 Jan - 2 January 2026
Wylder Tilghman Island

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (668)
"Great view, good ambiance all around"
United States
Dianne
The price is SAR 436
SAR 483 total
includes taxes & fees
4 Dec - 5 Dec
Hyatt Place Kent Narrows & Marina
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 St. Michaels Hotel Reviews

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Frequently asked questions

What are some accommodations with pools in St. Michaels?
St Michaels Inn: Features daily, a seasonal outdoor pool, and free self parking. Inn at Perry Cabin: Offers a full-service spa, an outdoor pool, and 2 bars. The Wildset: Features free self parking, an outdoor pool, and complimentary wireless internet access. George Brooks House B&B: Features complimentary wireless internet access, a communal pool, and kitchens. Parsonage Inn: Offers kitchens, a communal pool, and televisions.
What is there to see and do in St. Michaels?
Make a point to visit attractions like Church Cove Park and Chesapeake Bay Maritime Museum. Discover sights such as St. Michaels Marina, St. Michaels Winery, and Saint Michaels Town Hall during your stay. The seafood restaurants, historic landmarks, and shopping are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in St. Michaels?
You may want to consider an accommodation with an outdoor swimming pool if you plan to visit St. Michaels in the warmest months of July, August, or June when the average temperature is 75°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 41°F.