The Best Hotels with a Pool in St. Michaels, MD from NT$3,710 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. St Michaels Inn : Offers daily, a seasonal outdoor pool, and free self parking. The Wildset : Offers kitchens, a communal pool, and televisions. Parsonage Inn : Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. Historic Inns of Annapolis : Offers 2 outdoor pools, a children's pool, and a private beach.

The Chesapeake Bay Maritime Museum in Saint Michaels, Maryland, features the Hooper Strait Lighthouse, built in 1879

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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$4,682 total

includes taxes & fees

Jun 3 - Jun 4

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.

NT$6,194 total

includes taxes & fees

May 27 - May 28

Inn at Perry Cabin

Downtown St. Michaels

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

NT$23,047 total

includes taxes & fees

Jun 16 - Jun 17

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$11,766 total

includes taxes & fees

Jun 26 - Jun 27

Kent Island Resort

Stevensville

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

NT$6,451 total

includes taxes & fees

Jun 1 - Jun 2

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$6,218 total

includes taxes & fees

Jun 22 - Jun 23

Knapps Narrows Marina & Inn

Sherwood

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

NT$5,191 total

includes taxes & fees

May 27 - May 28

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$5,940 total

includes taxes & fees

May 31 - Jun 1

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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

Graduate by Hilton Annapolis

6/10 Okay

"We had a reservation for a king atrium room. When we checked in they said that room wasn’t ready but a two queen room was instead. It was implied the room was nicer and cost more. Instead of an atrium view we got a rooftop/parking lot view and a handicap room. The shower was extremely difficult to use without flooding the bathroom. Staff wasn’t interested in helping. The beds were extremely low and about two feet off the ground. No bathroom counter space as I had booked because the space was designed to accommodate a wheelchair. The closet was not usable because the rod was extremely low so someone in a wheelchair could reach it. But, the rod was just above the wall mounted safe so nothing could hang from it. Not a great experience for a very expensive stay."

Rod 'N' Reel Resort

6/10 Okay

"Bright refreshed renovated hotel. Large rooms, friendly staff, gambling slot machines not my thing but were busy. Restaurants were good, and staff were friendly. Only down side was the room doors were tricky and difficult to lock at times, and despite requesting housekeeping twice, over a four-day stay, they never came. Garbage cans overflowed, ran out of coffee, cups, tissues, and towels. Reported it, and manager said she would comp a night through the third party agent. I’ll watch for that remedy. Relaxing holiday weekend despite the rain out and lack of housekeeping."

Hampton Inn & Suites Annapolis

6/10 Okay

"Our room is shockingly awful. The appliances are dirty, primarily outside but I wouldn't use the microwave with a 10 foot pole. I always thought Hampton Inn and Suites was an upscale hotel. This looks like a Motel 6 or Super 8. I guess since it is pet friendly, it's assumed pet owners are dirty."

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. St Michaels Inn: Offers daily, a seasonal outdoor pool, and free self parking. The Wildset: Offers kitchens, a communal pool, and televisions. Parsonage Inn: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Offers 2 outdoor pools, a children's pool, and a private beach.

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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