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
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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 restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A hotel room with two beds, a chair, and a painting on the wall.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

1. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
AED 327
AED 360 total
includes taxes & fees
12 Oct - 13 Oct
St Michaels Inn
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
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.
A room with a view of a wooden deck and a gazebo by the water.

2. 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.
AED 1,884
AED 2,073 total
includes taxes & fees
26 Oct - 27 Oct
Inn at Perry Cabin
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.
An outdoor patio with a round wooden table and chairs, surrounded by potted plants and a brick wall.
A four-poster bed with a floral bedspread, a nightstand with a lamp, and a chair with a cushion.

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.
AED 918
AED 1,010 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 living room with a fireplace, a sofa, a chair, and a bookshelf.
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.

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.
AED 711
AED 782 total
includes taxes & fees
2 Nov - 3 Nov
George Brooks House B&B
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A spacious indoor dining area with large windows, tables, and chairs.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A modern lounge area with a fireplace, seating, and a view of the outdoors.

5. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
AED 680
AED 747 total
includes taxes & fees
5 Oct - 6 Oct
The Tilghman Island Inn
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 white colonial-style house with a covered porch, brick steps, and outdoor seating.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.

6. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
AED 1,616
AED 1,778 total
includes taxes & fees
5 Oct - 6 Oct
The Oaks Waterfront
A swimming pool with multiple people swimming and lounging around.
A waterfront property with houses, a dock, and a grassy area.
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.

7. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
AED 367
AED 404 total
includes taxes & fees
1 Nov - 2 Nov
Knapps Narrows Marina & Inn
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.
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.

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.
AED 474
AED 521 total
includes taxes & fees
5 Oct - 6 Oct
Best Western Plus Easton Inn & Suites
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 modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

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.
AED 492
AED 541 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Easton by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.
A waterfront hotel with a covered dock and a large building with multiple balconies.
A waterfront property with a covered patio, a dock, and a boat.

10. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
AED 794
AED 1,057 total
includes taxes & fees
18 Oct - 19 Oct
Wylder Tilghman Island
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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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The gym was really small. The rooms are very nice"
Henrik 2-night trip
Posted 1 hour ago
Rod 'N' Reel Resort
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great Hotel in a very central location"
Mark 2-night trip
Posted 19 hours ago
Graduate by Hilton Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 3 days ago
St Michaels Inn
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 13 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 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.