TOP Hotels with Swimming Pool in St. Michaels, MD for 2026

Q: 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 kitchens, a communal pool and televisions. Parsonage Inn : Provides kitchens, a communal pool and televisions. Historic Inns of Annapolis : Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool and complimentary wireless Internet access.

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

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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

Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.

₹9,235 total

includes taxes & fees

23 Aug - 24 Aug

George Brooks House B&B

St. Michaels

Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.

₹22,390 total

includes taxes & fees

28 Jul - 29 Jul

Inn at Perry Cabin

Downtown St. Michaels

Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.

₹66,313 total

includes taxes & fees

23 Aug - 24 Aug

Knapps Narrows Marina & Inn

Sherwood

Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.

₹15,880 total

includes taxes & fees

26 Jul - 27 Jul

The Tilghman Island Inn

Tilghman

Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.

₹23,819 total

includes taxes & fees

10 Aug - 11 Aug

Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.

₹12,264 total

includes taxes & fees

10 Aug - 11 Aug

Best Western Plus Easton Inn & Suites

Easton

Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.

₹14,715 total

includes taxes & fees

3 Aug - 4 Aug

Quality Inn

Easton

Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.

₹10,708 total

includes taxes & fees

11 Aug - 12 Aug

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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

10/10 Excellent

"Very dog and kid friendly ! They greeted us with cookies and bones . The pool was great as well as the location . We will be back"

Inn at Perry Cabin

10/10 Excellent

"Beautiful property, very well maintained. Dinner and Brunch at Stars were both very good. We loved being by the boats. Staff was accommodating when I had to do a zoom call on the morning of departure and found me a quiet private spot. Short walk to the Maritime Museum which was worth going to learn about the Eastern Shore. Short walk to town to pick up some needed items at the local pharmacy and on the way back stopped at the olive oil store and bought a couple of interesting bottles. Would have like to check out the SPA, but we decided on Friday to spend Saturday and Sunday nights and they were booked. The staff was generally friendly. It was expensive per night. But for clean and beautiful grounds, a clean room, friendly staff, and views from our room and from the restaurants that included water and boats, I felt it was worth it for our spontaneous road trip from the Philly suburb. We would come back and this time book a sailing activity and a massage. Notes: The big Samsung TV was nice but doesn't allow streaming from my phones and so we had to watch our show on my laptop. Room #2 was great in that it was in the main lodge next to the restaurant and a across from the bar which was very noisy at times. We didn't mind for 2 days, we enjoyed the convenience and drowned at noisy with a sound machine. If we were there for longer, the noise may have gotten old. In summary, we liked it and would visit again."

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 kitchens, a communal pool and televisions. Parsonage Inn: Provides kitchens, a communal pool and televisions. Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool and complimentary wireless Internet access.

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 Saint Michaels Town Hall, St. Michaels Marina and St. Michaels Winery 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.

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