A waterfront street lined with trees and a white building with a balcony.

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Check availability on St. Michaels Hotels with Pool

Tonight
12 Sep - 13 Sep
Tomorrow
13 Sep - 14 Sep
Next weekend
18 Sep - 20 Sep
In two weeks
25 Sep - 27 Sep

Our top choices for St. Michaels hotels with a pool

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A hotel room with two beds, a chair, and a painting on the wall.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

1. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
2.449.251 ₫
2.694.177 ₫ total
includes taxes & fees
13 Sept - 14 Sept
St Michaels Inn
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.
A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.
A living room with a fireplace, a sofa, a chair, and a bookshelf.

2. George Brooks House B&B

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.
5.481.657 ₫
6.029.823 ₫ total
includes taxes & fees
15 Sept - 16 Sept
George Brooks House B&B
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A room with a view of a wooden deck and a gazebo by the water.
A golf course with a water hazard and surrounding trees.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.

3. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
16.794.864 ₫
18.474.350 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Inn at Perry Cabin
A swimming pool with multiple people swimming and lounging around.
A covered patio area with wicker furniture and a view of a building with large windows.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.
A building with a sign reading "The Inn."

4. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
3.888.000 ₫
4.276.800 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Knapps Narrows Marina & Inn
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
A large building with a swimming pool, dock, and green surroundings.
A spacious indoor dining area with large windows, tables, and chairs.

5. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
5.313.190 ₫
5.844.509 ₫ total
includes taxes & fees
16 Sept - 17 Sept
The Tilghman Island Inn
A swimming pool with a white fence, lounge chairs, and umbrellas.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A modern food court with a central island, various food stations, and a yogurt display.

6. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
3.058.324 ₫
3.394.741 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
A hotel with a covered entrance, multiple floors, and a parking lot.
A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

7. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
  • Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.
3.503.088 ₫
3.853.397 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Fairfield Inn & Suites by Marriott Easton
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

8. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
  • Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
3.343.422 ₫
3.677.764 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Best Western Plus Easton Inn & Suites
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.
A kitchen with a stone wall, a microwave, and various food items on the counter.
A residential area with a large building, a swimming pool, and well-maintained lawns.

9. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
2.542.815 ₫
2.797.097 ₫ total
includes taxes & fees
20 Sept - 21 Sept
Baymont by Wyndham Easton
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A modern hotel dining area with a long table, four chairs, and three pendant lights.

10. Hampton Inn Easton

Hampton Inn Easton
Easton
  • Dive into refreshing luxury at this Easton hotel with a pristine indoor pool and fitness centre for your aquatic escape.
4.029.731 ₫
4.432.756 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Hampton Inn Easton
View all properties

Choose what matters most at hotels with a pool in St. Michaels

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top St. Michaels Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great stay- Go Navy Beat Army!"
Heather 2-night trip
Posted 5 hours ago
Graduate by Hilton Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"There was a glitch after sign in. We were locked out of our room and informed to come to the office immediately. When we went to the desk we were informed we'd been given the wrong room. We received new door cards and stayed in the same room and other guests had their room changed. The issue came up again at check-out. It is a nice hotel with many updates."
Charles 1-night trip
Posted 8 hours ago
St Michaels Inn
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"The room was clean and comfortable, however when i went to check out the élévator on my floor was n"
Jena 2-night trip
Posted 10 hours ago
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"All good."
Rod 1-night trip
Posted 12 hours ago
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"great place good price"
Adam 4-night trip
Posted 15 hours ago
Sonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"Great stay! Very clean and kind staff. The amenities close much too early (8pm), making them difficult to enjoy."
Jessica 1-night trip
Posted 1 day ago
Rod 'N' Reel Resort
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

8/10 Good
"Nice location to get to the Maryland REN Faire, Annapolis and multiple restaurants and shopping opportunities"
joe 3-night trip
Posted 4 days ago
Courtyard by Marriott Annapolis
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Susan 1-night trip
Posted 4 days ago
Inn at Perry Cabin
George Brooks House B&B

George Brooks House B&B

8/10 Good
"We enjoyed our stay but found a few things that could have been better. Our host (Will) was not present the first day and most likely did not know the coffee and tea bar had sour milk and no sugar. I took it upon myself to rummage around and find these things but I would have liked it better if they were there. Also, we had a scrap of toilet paper in our room and no refills so I had to find that as well. Small things but not a good first impression. Otherwise, the room was very comfortable, the pool was great and the breakfast was delicious."
Donna 2-night trip
Posted 3 weeks ago
George Brooks House B&B

Frequently asked questions

What is there to see and do in St. Michaels?
Make a point to visit attractions such as 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 accommodation that has an outdoor pool if you'll be visiting St. Michaels in the warmest months of July, August or June, when the average temperature is 24°C. Accommodation with an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temp is 5°C.

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