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

Hotels with Swimming Pool in St. Michaels, Maryland

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Check availability on St. Michaels Hotels with Swimming Pool

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
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 room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.
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.
P30,916
P34,007 total
includes taxes & fees
Nov 18 - Nov 19
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 conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

2. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
P5,045
P5,549 total
includes taxes & fees
Nov 1 - Nov 2
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.
P15,745
P17,320 total
includes taxes & fees
Nov 2 - Nov 3
Parsonage Inn
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A living room with a fireplace, a sofa, a chair, and a bookshelf.
A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.
A two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.

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.
P12,187
P13,405 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 wooden console table with framed floral artwork, two lamps, and two ottomans.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

5. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
P27,718
P30,489 total
includes taxes & fees
Oct 20 - Oct 21
The Oaks Waterfront
An indoor swimming pool with a tiled edge, lounge chairs, and a no diving sign.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A bathroom with a toilet, a sink, and a mirror. There are towels on a rack above the toilet and a towel on the sink counter.
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

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.
P9,384
P10,322 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Easton by IHG
A swimming pool with multiple people swimming and lounging around.
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.
A covered patio area with wicker furniture and a view of a building with large windows.

7. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
P9,447
P10,392 total
includes taxes & fees
Oct 20 - Oct 21
Knapps Narrows Marina & Inn
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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.

8. 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.
P8,512
P9,363 total
includes taxes & fees
Oct 25 - Oct 26
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 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.
P7,495
P8,244 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.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A large building with a swimming pool, dock, and green surroundings.
A modern lounge area with a fireplace, seating, and a view of the outdoors.

10. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
P11,651
P12,816 total
includes taxes & fees
Oct 20 - Oct 21
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Great location. Very clean."
scott 2-night trip
Posted 5 hours ago
St Michaels Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

8/10 Good
"Nice place, dinner staff was super slow but overall nice stay"
Richard 1-night trip
Posted 9 hours ago
Hyatt Regency Chesapeake Bay
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Extremely spacious, nicely appointed room."
r 1-night trip
Posted 10 hours ago
Graduate by Hilton Annapolis
Best Western Annapolis

Best Western Annapolis

8/10 Good
"We stay here regularly , 12 day trip this time."
scott 11-night trip
Posted 11 hours ago
Best Western Annapolis

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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