🏊 Top 10 Annapolis Hotels with Swimming Pool

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Annapolis Hotels with Swimming Pools

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Annapolis hotels with a pool

An outdoor pool area with lounge chairs and an umbrella.

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

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

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

1. Fort Davidson Hotel

Ironton

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

RM490

RM535 total

includes taxes & fees

27 Oct - 28 Oct

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

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

A spacious kitchen with a dining area, featuring a ceiling fan, a TV mounted on the wall, and a large rug in the center.

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

2. Madison Inn Lodge

Fredericktown

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

RM357

RM390 total

includes taxes & fees

11 Oct - 12 Oct

View all properties

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

"Nice and clean friendly staff"

Frequently asked questions

What are some accommodation options with pools in Annapolis?

Madison Inn Lodge: Features continental, a seasonal outdoor pool and free self parking. Shepherd Mountain Inn: Provides complimentary high-speed (wired) Internet access, an outdoor pool and free self parking.

What is there to see and do in Annapolis?

The picturesque setting of K Bridge Recreation Area and Mark Twain National Forest 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.

Room 1

Change your mind

Treat yourself

Be picky