Search Hotels with Pool in St. Michaels

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Check availability on St. Michaels Hotels with Pool

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for St. Michaels hotels with a pool

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1001)
"Staff was friendly, courteous, and helpful."
United States
Donna
The price is ฿3,159
฿3,475 total
includes taxes & fees
4 Jan - 5 Jan 2026
St Michaels Inn
Exterior
George Brooks House B&B

George Brooks House B&B

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 ฿4,805
฿5,286 total
includes taxes & fees
1 Jan - 2 Jan 2026
George Brooks House B&B
Porch
Parsonage Inn

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is ฿6,282
฿6,910 total
includes taxes & fees
1 Jan - 2 Jan 2026
Parsonage Inn
Outdoor pool
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is ฿16,395
฿19,838 total
includes taxes & fees
23 Dec - 24 Dec
Inn at Perry Cabin
Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1004)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is ฿2,859
฿3,802 total
includes taxes & fees
28 Dec - 29 Dec
Rod 'N' Reel Resort
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is ฿3,701
฿5,453 total
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island
Exterior
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (432)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is ฿5,182
฿6,551 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Chesapeake Bay Beach Club
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (938)
"It was very comfortable and clean"
United States
Maria
The price is ฿2,733
฿3,033 total
includes taxes & fees
29 Dec - 30 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (129)
"Beautiful and peaceful property!"
United States
Jerry
The price is ฿4,505
฿6,123 total
includes taxes & fees
23 Dec - 24 Dec
Kent Island Resort
Indoor pool
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
2.5 star property
Cambridge
8.2 out of 10, Very good, (797)
"Staff was very accommodating and the hotel was clean with very good breakfast."
United States
salema
The price is ฿3,310
฿3,675 total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Cambridge
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.
View all properties

Top St. Michaels Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"It was clean, quiet and comfortable. Will definitely come back if in the area again."
Nick 2-night trip
Posted 5 days ago
Country Inn & Suites by Radisson, Annapolis, MD
George Brooks House B&B

George Brooks House B&B

10/10 Excellent
"We were in St. Michaels for a wedding. We are planning on returning for a longer stay in the future. "
Andy 1-night trip
Posted 2 months ago
George Brooks House B&B

Frequently asked questions

What are some accommodation options with pools in St. Michaels?
Inn at Perry Cabin: Features a full-service spa, an outdoor pool and 2 bars. St Michaels Inn: Offers daily, a seasonal outdoor pool and free self parking. The Wildset: Features free self parking, an outdoor pool and complimentary wireless Internet access. George Brooks House B&B: Features kitchens, a communal pool and televisions. Parsonage Inn: Offers complimentary wireless Internet access, a communal pool and kitchens.
What is there to see and do in St. Michaels?
Make a point to visit attractions such as Church Cove Park and Chesapeake Bay Maritime Museum. Discover sights such as St. Michaels Marina, St. Michaels Winery and Saint Michaels Village 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 accommodation that has an outdoor pool if you'll be visiting St. Michaels in the warmest months of July, August or June, when the average temperature is 24°C. Accommodation with an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temp is 5°C.