Search Hotels with Pool in St. Michaels

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Check availability on St. Michaels Hotels with Pool

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, (1000)
"clean and comfy, friendly staff"
United States
Tamara
The price is Rp1.853.987
Rp2.039.385 total
includes taxes & fees
15 Dec - 16 Dec
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 Rp2.553.264
Rp2.808.590 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 Rp3.335.200
Rp3.668.720 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 Rp7.840.022
Rp9.486.460 total
includes taxes & fees
14 Dec - 15 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, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is Rp1.773.242
Rp2.301.819 total
includes taxes & fees
11 Jan - 12 Jan 2026
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 Rp2.252.880
Rp3.212.440 total
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island
Outdoor pool
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is Rp2.236.252
Rp2.549.427 total
includes taxes & fees
1 Jan - 2 Jan 2026
Anchored Inn at Hidden Harbour Marina
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, (793)
"It was a nice comfortable room convenient to our travels and at a great price. "
United States
Ann
The price is Rp1.774.660
Rp1.969.873 total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Cambridge
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, (932)
"It was very comfortable and clean"
United States
Maria
The price is Rp1.451.856
Rp1.611.560 total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (360)
"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 Rp2.001.120
Rp2.201.232 total
includes taxes & fees
12 Dec - 13 Dec
Knapps Narrows Marina & Inn
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

Frequently asked questions

What are some accommodation options 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 such as 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 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.