The Best Hotels with a Pool in St. Michaels, MD from NT$3,101 in 2026

Q: What are some accommodations 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 : Offers free self parking, an outdoor pool, and complimentary wireless internet access. George Brooks House B&B : Features kitchens, a communal pool, and televisions.

Oxford to Bellevue Ferry, Maryland, continuous use from 1683 to 1836

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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.

NT$3,101 total

includes taxes & fees

Jul 20 - Jul 21

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.

NT$11,832 total

includes taxes & fees

Jun 26 - Jun 27

Inn at Perry Cabin

Downtown St. Michaels

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

NT$22,550 total

includes taxes & fees

Jul 9 - Jul 10

Knapps Narrows Marina & Inn

Sherwood

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

NT$5,220 total

includes taxes & fees

Jun 25 - Jun 26

Inn at Huntingfield Creek

Rock Hall

Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.

NT$6,253 total

includes taxes & fees

Jul 6 - Jul 7

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

Rod 'N' Reel Resort

Chesapeake Beach

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

NT$6,290 total

includes taxes & fees

Jun 29 - Jun 30

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

Kent Island Resort

Stevensville

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

NT$6,596 total

includes taxes & fees

Jul 1 - Jul 2

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

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

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

NT$4,706 total

includes taxes & fees

Jul 20 - Jul 21

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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

Sonesta ES Suites Annapolis

8/10 Good

"Great breakfast, nice pool and fire pit. We were on 1st floor. Condo was nice, but could hear a lot from condo above us. A lot of people smoking pot on property too. Pool area needs someone to go in there and clean debris around fence line and I think they should upgrade the pool towels."

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Very nice room -- really a suite with two rooms, a closing door between them, and two work-ready desks. Our only complaint was noise. The building seemed to rattle and roll at the slightest provocation: the AC fan was very noisy, we could hear showers from other rooms, and even the breakfast room floor shook as folks walked across it or machinery turned on and off."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"It was our first time in the area so this hotel made the experience great all around. Everything was clean, the food was super good too! We ate breakfast two days in a row and ordered dinner and all meals were hot, fresh and delicious. The area where the hotel is at is convenient but it seems the gps isn’t the best for getting around as our transportation from the airport got lost and we had uber drivers get lost as well, but we walked across the street to the mall twice and it’s fairly quick and easy to get to and there are a good amount of restaurants near by"

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. 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: 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.

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