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
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for St. Michaels hotels with a pool

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.

1. 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.
฿17,201
฿18,921 total
includes taxes & fees
8 Nov - 9 Nov
Inn at Perry Cabin
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A hotel room with two beds, a chair, and a painting on the wall.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

2. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
฿2,867
฿3,153 total
includes taxes & fees
1 Nov - 2 Nov
St Michaels Inn
A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.
A cozy room with a fireplace, a framed picture above it, and two armchairs.
A four-poster bed with a floral bedspread, a nightstand with a lamp, and a chair with a cushion.
An outdoor patio with a round wooden table and chairs, surrounded by potted plants and a brick wall.

3. Parsonage Inn

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.
฿8,383
฿9,221 total
includes taxes & fees
2 Nov - 3 Nov
Parsonage 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.

4. 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.
฿6,488
฿7,137 total
includes taxes & fees
2 Nov - 3 Nov
George Brooks House B&B
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

5. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
฿14,757
฿16,232 total
includes taxes & fees
12 Oct - 13 Oct
The Oaks Waterfront
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 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.
A hotel with a covered entrance, multiple floors, and a parking lot.

6. 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.
฿4,532
฿4,985 total
includes taxes & fees
18 Oct - 19 Oct
Fairfield Inn & Suites by Marriott Easton
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
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 spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

7. 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.
฿4,325
฿4,758 total
includes taxes & fees
12 Oct - 13 Oct
Best Western Plus Easton Inn & Suites
A swimming pool with multiple people swimming and lounging around.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.
A covered patio area with wicker furniture and a view of a building with large windows.
A building with a sign reading "The Inn."

8. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
฿5,030
฿5,532 total
includes taxes & fees
12 Oct - 13 Oct
Knapps Narrows Marina & Inn
An indoor swimming pool with a 'NO LIFEGUARD ON DUTY' sign, lounge chairs, and potted plants.
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.

9. Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
  • Splashy indoor pool retreat creates a refreshing escape in the heart of Easton.
฿4,996
฿5,496 total
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Express Easton by IHG
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A large building with a swimming pool, dock, and green surroundings.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A spacious indoor dining area with large windows, tables, and chairs.

10. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
฿6,203
฿6,823 total
includes taxes & fees
12 Oct - 13 Oct
The Tilghman Island Inn
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Overall a great place to stay, very clean, and updated, price was more then expected, breakfast should of been included. Also a lot of hidden fees. Overall enjoyed our stay. Free parking was a plus. I am thinking about returning for my 60th birthday."
Ulysses 1-night trip
Posted 16 hours ago
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

10/10 Excellent
"We travel to St micheals md, several times a year, during the oyster season. Usually we stay at hotels in easton, so this time we tried the st micheals inn. It's closer to the Cheasapeake Landing restaurant. We were placed in a room opposite the main street, which made for a very quiet evening. Much better than those hotels off rt.50. The breakfast was a "hot" breakfast and included with the stay. The beds are comfortable, and the showers hot and forceful."
William 1-night trip
Posted 21 hours ago
St Michaels Inn
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Easy parking. Super comfy bed."
Kristen 1-night trip
Posted 2 days ago
The Westin Annapolis
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 2 months ago
George Brooks House B&B

Frequently asked questions

What are some accommodation options with pools in St. Michaels?
St Michaels Inn: Features daily, a seasonal outdoor pool and free self parking. Inn at Perry Cabin: Offers a full-service spa, an outdoor pool and 2 bars. The Wildset: Features free self parking, an outdoor pool and complimentary wireless Internet access. George Brooks House B&B: Offers kitchens, a communal pool and televisions. Parsonage Inn: Offers kitchens, a communal pool and televisions.
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 Saint Michaels Town Hall, St. Michaels Marina and St. Michaels Winery 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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