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 10 - Oct 11
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Oct 11 - Oct 12
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Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for St. Michaels hotels with a pool

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.
A room with a view of a wooden deck and a gazebo by the water.
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.
NT$16,378
NT$18,016 total
includes taxes & fees
Nov 8 - Nov 9
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 reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

2. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
NT$2,730
NT$3,003 total
includes taxes & fees
Nov 8 - Nov 9
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 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.
A cozy room with a fireplace, a framed picture above it, and two armchairs.

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.
NT$7,982
NT$8,780 total
includes taxes & fees
Nov 3 - Nov 4
Parsonage Inn
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.
A four-poster bed with a floral bedspread, a large bathtub, and a chair in a room with green walls and wooden floors.
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.
NT$6,178
NT$6,795 total
includes taxes & fees
Nov 2 - Nov 3
George Brooks House B&B
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.
NT$14,051
NT$15,456 total
includes taxes & fees
Oct 11 - Oct 12
The Oaks Waterfront
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
A hotel with a covered entrance, multiple floors, and a parking lot.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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.

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.
NT$4,315
NT$4,746 total
includes taxes & fees
Oct 18 - Oct 19
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.

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.
NT$4,118
NT$4,530 total
includes taxes & fees
Oct 13 - Oct 14
Best Western Plus Easton Inn & Suites
A swimming pool with multiple people swimming and lounging around.
A building with a sign reading "The Inn."
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.

8. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
NT$4,789
NT$5,268 total
includes taxes & fees
Oct 11 - Oct 12
Knapps Narrows Marina & Inn
An indoor swimming pool with a 'NO LIFEGUARD ON DUTY' sign, lounge chairs, and potted plants.
A coffee station with two coffee machines and a variety of coffee pods and cups.
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.

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.
NT$4,757
NT$5,233 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Express Easton by IHG
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

10. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
  • Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
NT$4,853
NT$5,387 total
includes taxes & fees
Oct 18 - Oct 19
Hyatt Place Kent Narrows & Marina
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

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Easy parking. Super comfy bed."
Kristen 1-night trip
Posted 14 hours ago
The Westin Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 9 days ago
St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."
Christina 2-night trip
Posted 11 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 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. 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 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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