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

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Check availability on St. Michaels Hotels with a Pool

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for St. Michaels hotels with a pool

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.
A white house with a garden patio featuring a wicker chair and a round table.
A golf course with a water hazard and surrounding trees.

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.
￥81,064
￥89,170 total
includes taxes & fees
Nov 11 - Nov 12
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 conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
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.
￥12,657
￥13,923 total
includes taxes & fees
Nov 1 - Nov 2
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 four-poster bed with a floral bedspread, a large bathtub, and a chair in a room with green walls and wooden floors.
A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.

3. 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.
￥30,577
￥33,635 total
includes taxes & fees
Nov 2 - Nov 3
George Brooks House B&B
A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.
A bathroom with a toilet, sink, and window with curtains.
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.

4. 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.
￥39,505
￥43,456 total
includes taxes & fees
Nov 2 - Nov 3
Parsonage Inn
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
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.
￥69,545
￥76,499 total
includes taxes & fees
Oct 18 - Oct 19
The Oaks Waterfront
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 modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.
A coffee station with two coffee machines and a variety of coffee pods and cups.

6. 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.
￥23,545
￥25,899 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Express Easton by IHG
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
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.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

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.
￥21,356
￥23,493 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites by Marriott Easton
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 waterfront property with houses, a dock, and a grassy area.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

8. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
￥23,703
￥26,073 total
includes taxes & fees
Oct 18 - Oct 19
Knapps Narrows Marina & Inn
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 hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

9. 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.
￥18,804
￥20,684 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Easton Inn & Suites
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.

10. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
￥29,234
￥32,157 total
includes taxes & fees
Oct 19 - Oct 20
The Tilghman Island Inn
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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
"Clean room, very nice decor and great staff"
Nadine 2-night trip
Posted 1 day ago
Graduate by Hilton Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 1 day ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 6 days ago
Sonesta ES Suites 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 accommodations 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. John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!: Offers kitchens, a communal pool, and televisions.
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 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 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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