The Best Hotels with a Pool in St. Michaels, MD from AED 329 in 2026

Q: What are some accommodations with pools in St. Michaels?

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

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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.

AED 460 total

includes taxes & fees

2 Jun - 3 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.

AED 723 total

includes taxes & fees

11 May - 12 May

Inn at Perry Cabin

Downtown St. Michaels

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

AED 2,436 total

includes taxes & fees

31 May - 1 Jun

Best Western Plus Easton Inn & Suites

Easton

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

AED 440 total

includes taxes & fees

11 May - 12 May

Kent Island Resort

Stevensville

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

AED 856 total

includes taxes & fees

11 May - 12 May

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.

AED 593 total

includes taxes & fees

17 May - 18 May

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.

AED 546 total

includes taxes & fees

27 May - 28 May

Inn at Huntingfield Creek

Rock Hall

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

AED 736 total

includes taxes & fees

11 May - 12 May

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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

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Great location with good breakfast. 👍"

DoubleTree by Hilton Hotel Annapolis

4/10 Poor

"we paid a premium rate for what we expected to be an upscale property. The lobby represented what we expected, however, the room was anything but. Everything looked old and tired. The chair had holes in the upholstery. The bathroom fan was noisy. It was a handicap room. The shower leaked all over the bathroom. It was a definite slip and fall hazard"

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Frequently asked questions

What are some accommodations with pools in St. Michaels?

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