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

Hotels with Swimming Pools in St. Michaels

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Check availability on St. Michaels Hotels with Swimming Pools

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
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 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 hotel room with two beds, a chair, and a painting on the wall.

1. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
S$125
includes taxes & fees
6 Oct - 7 Oct
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 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.

2. 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.
S$351
includes taxes & fees
2 Nov - 3 Nov
Parsonage 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.

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.
S$721
includes taxes & fees
3 Nov - 4 Nov
Inn at Perry Cabin
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.
S$272
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.
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.
A spacious indoor dining area with large windows, tables, and chairs.

5. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
S$260
includes taxes & fees
6 Oct - 7 Oct
The Tilghman Island Inn
A swimming pool with multiple people swimming and lounging around.
A waterfront property with houses, a dock, and a grassy area.
A building with a sign reading "The Inn."
A covered patio area with wicker furniture and a view of a building with large windows.

6. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
S$141
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 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.

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.
S$181
includes taxes & fees
6 Oct - 7 Oct
Best Western Plus Easton Inn & Suites
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.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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.
S$190
includes taxes & fees
11 Oct - 12 Oct
Fairfield Inn & Suites by Marriott Easton
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 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.

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.
S$188
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Easton by IHG
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.
A modern hotel dining area with a long table, four chairs, and three pendant lights.

10. Hampton Inn Easton

Hampton Inn Easton
Easton
  • Dive into refreshing luxury at this Easton hotel with a pristine indoor pool and fitness centre for your aquatic escape.
S$180
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn Easton
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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

Best Western Annapolis

Best Western Annapolis

8/10 Good
"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."
Silvia 1-night trip
Posted 10 hours ago
Best Western Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"It is an excellent value for the cost!"
Nancy 1-night trip
Posted 15 hours ago
Sonesta ES Suites Annapolis
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 20 hours ago
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 4 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 6 days ago
Inn at Perry Cabin
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 2 weeks 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 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: 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 such as 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 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.

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