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

St. Michaels Hotel Guide - Hotels with Pool in St. Michaels, Maryland

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Check availability on St. Michaels Hotels with Pool

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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 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.

1. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
€84
includes taxes & fees
31 Aug - 1 Sept
St Michaels 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 two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.

2. 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.
€199
includes taxes & fees
31 Aug - 1 Sept
George Brooks House B&B
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 room with a view of a wooden deck and a gazebo by the water.
A golf course with a water hazard and surrounding trees.

3. 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.
€419
includes taxes & fees
7 Sept - 8 Sept
Inn at Perry Cabin
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
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.

4. 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.
€131
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Easton Inn & Suites
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 building with a sign reading "The Inn."

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
€142
includes taxes & fees
30 Aug - 31 Aug
Knapps Narrows Marina & Inn
A swimming pool with lounge chairs and a covered area, surrounded by a fence and buildings.
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A modern building with large windows, a brick facade, and a well-maintained lawn with flower beds.
A hotel reception area with a wooden counter, a large sailboat painting, and a waffle station.

6. Quality Inn

Quality Inn
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
€150
includes taxes & fees
28 Aug - 29 Aug
Quality Inn
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
An outdoor bar area with a view of the lake, wooden deck, and metal roof structure.
A spacious indoor dining area with large windows, tables, and chairs.
A large building with a swimming pool, dock, and green surroundings.

7. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
€194
includes taxes & fees
31 Aug - 1 Sept
The Tilghman Island Inn
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.

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.
€127
includes taxes & fees
13 Sept - 14 Sept
Fairfield Inn & Suites by Marriott Easton
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.
An indoor swimming pool with lounge chairs and a no diving sign.
A Holiday Inn Express building with a brick facade, a green roof, and a flagpole with a flag.
A Holiday Inn Express hotel with a brick facade, a green roof, and a flagpole with the American flag.

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.
€150
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Express Easton by IHG
A swimming pool with a mural, lounge chairs, and a hot tub.
A hotel room with a large bed, a separate sitting area, a bathtub, and a view of the outdoors.
A multi-story hotel with a central courtyard, a flag, and a sign indicating it is a Radisson hotel.
A bathroom with a marble countertop, a sink, a mirror with a gold frame, a hair dryer, toiletries, and a view of the outside.

10. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
€113
includes taxes & fees
7 Sept - 8 Sept
Best Western Kent Narrows 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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Three pools and a hot tub are great. Took advantage of kayak rental on the premises. Our room was clean and the staff were very helpful and friendly."
Sandra 2-night trip
Posted 6 hours ago
Hyatt Regency Chesapeake Bay
St Michaels Inn

St Michaels Inn

8/10 Good
"My room was wonderful! Great comfort of the bed. Peaceful. The breakfast was lack luster with all carbs. Nothing sugar free for diabetics. Lots of construction and painting during my stay. Would stay here again, however!"
Kris 3-night trip
Posted 7 hours ago
St Michaels Inn
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good
"The A/C was really loud when it turned on and off. Otherwise, our stay was fine."
Lee Anee 1-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Annapolis, MD
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The staff went out of their way for me and I complimented them on how well they took care of the property"
James 1-night trip
Posted 16 hours ago
Rod 'N' Reel Resort
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"I arrived late following a long-distance sailboat race across the Chesapeake Bay. “Nick” was managing the front desk. He was polite, efficient, friendly, and professional. He offered me the best room the hotel had available at my price, and guaranteed I would have a good night’s rest. He was 100% correct. The room was clean and comfortable, and more importantly it was quiet. Check out was easy the next morning."
maurice 1-night trip
Posted 2 days ago
Graduate by Hilton Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

8/10 Good
"I wish I could give half stars because this place is really a 4.5 stars. First off this place was great, it is everything you need for a hotel. Great prices, friendly staff, very clean, very nice hotel. Why I gave it 4 stars? The coffee machine was down for our first night, the jacuzzi was down for maintenance, the wifi went for maintenance lol so it was a little much but I know you can't always control those things. Another small thing, I also wish the TV's were smart TV's and I wish the rooms came with a microwave. Overall great hotel, would stay here again."
Joseph 3-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean room and staff was very courteous."
Daetonya 1-night trip
Posted 4 days ago
Courtyard by Marriott 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 7 days 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: Features 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 St. Michaels Marina, St. Michaels Winery and Saint Michaels Village 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.