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

Search Hotels with Swimming Pool in St. Michaels

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Check availability on St. Michaels Hotels with Swimming Pool

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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 bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.
A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

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.
₹46,598
₹51,257 total
includes taxes & fees
18 Nov - 19 Nov
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 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.
A hotel room with two beds, a chair, and a painting on the wall.

2. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
₹7,147
₹7,862 total
includes taxes & fees
19 Nov - 20 Nov
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 living room with a fireplace, a sofa, a chair, and a bookshelf.

3. 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.
₹18,368
₹20,205 total
includes taxes & fees
3 Nov - 4 Nov
George Brooks House B&B
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.
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.

4. 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.
₹23,732
₹26,105 total
includes taxes & fees
3 Nov - 4 Nov
Parsonage 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 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.

5. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
₹41,777
₹45,955 total
includes taxes & fees
21 Oct - 22 Oct
The Oaks Waterfront
An indoor swimming pool with a tiled edge, lounge chairs, and a no diving sign.
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.
A coffee station with two coffee machines and a variety of coffee pods and cups.

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.
₹14,149
₹15,564 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Easton by IHG
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.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

7. 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.
₹12,829
₹14,112 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Easton
A swimming pool with multiple people swimming and lounging around.
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."
A waterfront property with houses, a dock, and a grassy area.

8. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
₹14,239
₹15,663 total
includes taxes & fees
21 Oct - 22 Oct
Knapps Narrows Marina & Inn
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 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.
₹11,296
₹12,426 total
includes taxes & fees
15 Nov - 16 Nov
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 modern lounge area with a fireplace, seating, and a view of the outdoors.
A large building with a swimming pool, dock, and green surroundings.

10. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
₹16,612
₹18,273 total
includes taxes & fees
25 Oct - 26 Oct
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
"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."
Kelly 4-night trip
Posted 17 hours ago
St Michaels Inn
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"Super nice staff, Clean rooms, comfortable bed, good breakfast and close to restaurants and less than 5miles to City Dock. I was in Annapolis for work for 5 days, I recommend this hotel, thank you!"
Teri 5-night trip
Posted 23 hours ago
Best Western Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

8/10 Good
"My husband and I were traveling with our 14 month-old son. The room was a good size and had two separate bedrooms, which worked out really well for us. There was a strong odor when we first arrived to our room. We travel with an air purifier for our son, as he sometimes has sinus issues, so that helped. The room itself was a bit dated, although well laid out. The fridge, microwave and dishwasher were all really nice to have. We didn’t get to use the fireplace, as we purchased a log, but we didn’t have a lighter or matches and the property didn’t either. The breakfast every morning was great! Fresh food snd fresh ingredients. Kitchen staff was incredibly friendly and good with our son, too. I’d say 7.5/10, but if they were to update the room and eliminate the odor, I feel like it’d be a 9/10."
Shoshana 2-night trip
Posted 1 day ago
Sonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Loved the balcony."
Hildehardo F 4-night trip
Posted 1 day ago
Rod 'N' Reel Resort
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 2 days ago
Hyatt Regency Chesapeake Bay

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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