Top Hotels with Swimming Pools in Annapolis

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Our top choices for Annapolis hotels with a pool

An outdoor pool area with lounge chairs and an umbrella.

A two-story building with a green roof and a large circular sign that reads "Port David Restaurant".

A hotel room with a television, a desk, a chair, a dresser, a radiator, and a bathroom visible through an open door.

A reception desk with a woman standing behind it, a man with a suitcase, and another person standing to the left.

1. Fort Davidson Hotel

Ironton

Dive into scenic pool days at Fort Davidson hotel with plush loungers for ultimate relaxation.

S$174

includes taxes & fees

31 Aug - 1 Sept

A rectangular pool with a metal ladder, surrounded by a white fence. There are two blue umbrellas and a table with chairs.

A motel with a covered entrance, a flag, and a phone number.

A reception desk with a wooden finish, a framed black and white cityscape, and a large framed Eiffel Tower picture.

A hotel room with two beds, a desk, a chair, a TV, and a bathroom.

2. Madison Inn Lodge

Fredericktown

A seasonal outdoor pool awaits at this tranquil Madison escape with terrace views.

S$122

includes taxes & fees

8 Sept - 9 Sept

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Choose what matters most at hotels with a pool in Annapolis

Breakfast included

4 stars

5 stars

Hot tub

Spa

Top Annapolis Hotel Reviews

Madison Inn Lodge

10/10 Excellent

"Great experience"

Fort Davidson Hotel

10/10 Excellent

"Clean rooms , nice pool."

Frequently asked questions

What are some accommodation options with pools in Annapolis?

Shepherd Mountain Inn: Features continental, a seasonal outdoor pool and free self parking. Madison Inn Lodge: Features complimentary high-speed (wired) Internet access, an outdoor pool and free self parking. Black River Motel and Restaurant: Offers a private beach, a seasonal outdoor pool and full.

What is there to see and do in Annapolis?

The picturesque setting of Mark Twain National Forest and K Bridge Recreation Area showcase the area's natural beauty. Discover sights such as Taum Sauk Mountain State Park, Walnut Hollow Lake and Ketcherside Mountain Conservation Area during your stay.

When is the best time to book a hotel with a pool in Annapolis?

You may want to consider a place to stay that offers an outdoor pool if you'll be visiting Annapolis in the warmest months of July, August or June, when the average temp is 24°C. Accommodation with an indoor pool may be the way to go if you visit during the coldest months of January, February or December, when the average temperature is 4°C.

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