A waterfront street lined with trees and a white building with a balcony.

Find Hotels with a Pool in St. Michaels, MD

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Check availability on St. Michaels Hotels with a Pool

This weekend
Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

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
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is ₩176,414
₩194,055 total
includes taxes & fees
Jul 15 - Jul 16
St Michaels Inn
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (155 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is ₩248,040
₩327,110 total
includes taxes & fees
Jul 16 - Jul 17
Kent Island Resort
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (388 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is ₩227,925
₩250,718 total
includes taxes & fees
Jul 22 - Jul 23
Knapps Narrows Marina & Inn
Outdoor pool, sun loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is ₩270,593
₩300,345 total
includes taxes & fees
Jul 13 - Jul 14
Inn at Huntingfield Creek
Outdoor pool

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (491 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is ₩367,871
₩419,382 total
includes taxes & fees
Jul 12 - Jul 13
Anchored Inn at Hidden Harbour Marina
Front of property

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (17 reviews)
  • cleanliness
    Escape to a seasonal outdoor paradise with a hot tub and 24-hour pool access at this luxury bed & breakfast.
The price is ₩517,405
₩589,840 total
includes taxes & fees
Aug 2 - Aug 3
The Inn at Tacaro Estate
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

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, (1,004 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is ₩211,211
₩234,445 total
includes taxes & fees
Jul 15 - Jul 16
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,012 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is ₩324,314
₩410,588 total
includes taxes & fees
Jul 16 - Jul 17
Rod 'N' Reel Resort
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (930 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is ₩151,950
₩168,665 total
includes taxes & fees
Jul 29 - Jul 30
Quality Inn Grasonville near Kent Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,007 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is ₩190,226
₩211,150 total
includes taxes & fees
Jul 13 - Jul 14
Best Western Kent Narrows 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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Choose what matters most at hotels with a pool in St. Michaels

Breakfast included
Hot tub

Top St. Michaels Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Staff helpful with arranging transportation to harbor."
Shelley 1-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Annapolis

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. The Wildset: Provides a full-service spa, an outdoor pool, and 2 bars. Inn at Perry Cabin: Features kitchens, a communal pool, and televisions. Parsonage Inn: Offers free self parking, an outdoor pool, and complimentary wireless internet access. George Brooks House B&B: Features 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 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.