TOP Hotels with 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 : Offers kitchens, a communal pool and televisions. Parsonage Inn : Offers 2 outdoor swimming pools, a children's pool and a private beach. Historic Inns of Annapolis : Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool and complimentary wireless Internet access.

Aerial panorama of shipyard and lighthouse in St. Michaels harbor in Maryland in the Chesapeake Bay

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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.

Rp2.531.181 total

includes taxes & fees

28 Jun - 29 Jun

Parsonage Inn

Downtown St. Michaels

Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons.

Rp3.927.942 total

includes taxes & fees

22 Jun - 23 Jun

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.

Rp6.099.166 total

includes taxes & fees

12 Jun - 13 Jun

Inn at Perry Cabin

Downtown St. Michaels

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

Rp13.145.774 total

includes taxes & fees

1 Jul - 2 Jul

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, pool loungers

Kent Island Resort

Stevensville

Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.

Rp3.479.247 total

includes taxes & fees

16 Jun - 17 Jun

Knapps Narrows Marina & Inn

Sherwood

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

Rp2.960.760 total

includes taxes & fees

14 Jun - 15 Jun

Best Western Kent Narrows Inn

Grasonville

Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.

Rp2.182.995 total

includes taxes & fees

6 Jul - 7 Jul

Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)

Rod 'N' Reel Resort

Chesapeake Beach

Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.

Rp3.416.348 total

includes taxes & fees

18 Jun - 19 Jun

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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

"Just fantastic"

Country Inn & Suites by Radisson, Annapolis, MD

6/10 Okay

"The rooms are old and look like they had a cheap paint job. There was a used wash cloth left in my room and the hair dryer was gross and sticky to touch. The sheets and blanket were super thin. The bed wasn’t too comfortable. The lobby is nice and the location is super convenient, but I’d choose another place. Didn’t try breakfast or the pool."

Courtyard by Marriott Annapolis

10/10 Excellent

"Everything was perfect at this hotel. From Kim, at check-in, to having access to The Bistro until 10PM for snacks and beverages, coffee and cocktails, it was perfect. Incredibly clean and well maintained. The furniture in the rooms was high-end and beautiful. the rugs throughout were spotless. The sleeper sofa in our room was brand new, comfortable and just so appealing and pleasant. We asked for a late check out as we had a court case in Annapolis and they kindly extended check out for us. They all, bent over backwards to accommodate us and we truly appreciate that. I wish I could live there LOL!"

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: Offers kitchens, a communal pool and televisions. Parsonage Inn: Offers 2 outdoor swimming pools, a children's pool and a private beach. 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 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.

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