Find Hotels with a Pool in St. Michaels, MD

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Our top choices for St. Michaels hotels with a pool

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
$94 nightly
The price is $104
Jan 4 - Jan 5, 2026
Total with taxes and fees
St Michaels Inn

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
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
George Brooks House B&B

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
$200 nightly
The price is $220
Jan 1 - Jan 2, 2026
Total with taxes and fees
Parsonage Inn

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
$566 nightly
The price is $622
Dec 24 - Dec 25
Total with taxes and fees
Inn at Perry Cabin

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
$119 nightly
The price is $130
Dec 29 - Dec 30
Total with taxes and fees
Rod 'N' Reel Resort

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
$158 nightly
The price is $174
Jan 1 - Jan 2, 2026
Total with taxes and fees
Wylder Tilghman Island

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
$188 nightly
The price is $209
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club

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
$87 nightly
The price is $97
Dec 28 - Dec 29
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

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
$179 nightly
The price is $195
Dec 23 - Dec 24
Total with taxes and fees
Kent Island Resort

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
$105 nightly
The price is $117
Dec 29 - Dec 30
Total with taxes and fees
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.

Top St. Michaels Hotel Reviews

Frequently asked questions

What are some accommodations 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 like 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 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.

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