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

Find Hotels with a Pool in St. Michaels, MD

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Check availability on St. Michaels Hotels with a Pool

Tonight
Sep 7 - Sep 8
Tomorrow
Sep 8 - Sep 9
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

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 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 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.
$87 nightly
$96 total
Sep 20 - Sep 21
Total with taxes and fees
St Michaels 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 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.
$235 nightly
$259 total
Sep 9 - Sep 10
Total with taxes and fees
George Brooks House B&B
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A room with a view of a wooden deck and a gazebo by the water.
A white house with a garden patio featuring a wicker chair and a round table.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.

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.
$670 nightly
$737 total
Oct 6 - Oct 7
Total with taxes and fees
Inn at Perry Cabin
A swimming pool with multiple people swimming and lounging around.
A covered patio area with wicker furniture and a view of a building with large windows.
A building with a sign reading "The Inn."
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

4. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
$150 nightly
$165 total
Sep 9 - Sep 10
Total with taxes and fees
Knapps Narrows Marina & Inn
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
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.
An outdoor bar area with a view of the lake, wooden deck, and metal roof structure.

5. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
$205 nightly
$226 total
Sep 16 - Sep 17
Total with taxes and fees
The Tilghman Island 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 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.

6. 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.
$129 nightly
$142 total
Sep 27 - Sep 28
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A swimming pool with a white fence, lounge chairs, and umbrellas.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A modern food court with a central island, various food stations, and a yogurt display.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

7. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
$123 nightly
$137 total
Oct 6 - Oct 7
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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 lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
A hotel with a covered entrance, multiple floors, and a parking lot.

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.
$135 nightly
$149 total
Sep 13 - Sep 14
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
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 modern hotel dining area with a long table, four chairs, and three pendant lights.
A hotel hallway with carpeted floors, white doors, and overhead lighting.

9. Hampton Inn Easton

Hampton Inn Easton
Easton
  • Dive into refreshing luxury at this Easton hotel with a pristine indoor pool and fitness center for your aquatic escape.
$155 nightly
$170 total
Oct 1 - Oct 2
Total with taxes and fees
Hampton Inn Easton
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

10. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
  • Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
$152 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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Choose what matters most at hotels with a pool in St. Michaels

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top St. Michaels Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"The lawn around the tennis court and pool need cutting/landscaping. Other than that the room was great and felt like a safe location."
Tanya 4-night trip
Posted 1 hour ago
Sonesta ES Suites Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Nice place. Breakfast was great pool needs more chairs."
Patricia 1-night trip
Posted 2 hours ago
St Michaels Inn
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Helpful staff. We were in town for a USNA reunion, and the lobby café was surprisingly useful. Rendezvouses with classmates. Late evening bulk sessions. Decent coffee and snacks. Walking distance to stadium park n ride."
David 4-night trip
Posted 5 hours ago
Courtyard by Marriott Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Felt like we traveled to a southern town while still being in Maryland. Great hotel."
Michael 1-night trip
Posted 6 hours ago
Rod 'N' Reel Resort
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"GREAT location! The room was huge & beautifully decorated. We are excited to come back again! 10/10!"
Lori Ann 1-night trip
Posted 9 hours ago
Graduate by Hilton Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Great hotel! Wish the microwave was in the room."
Eric 1-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Would definitely return in the near future. My family had fun."
Abdoul Latif 1-night trip
Posted 2 days ago
Hyatt Regency Chesapeake Bay
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 3 weeks ago
George Brooks House B&B

Frequently asked questions

What are the best hotels in St Michaels with outdoor pools?
The Inn at Perry Cabin is a stunning 5-star hotel that offers an exceptional outdoor pool experience, rated highly by guests with an impressive score of 9.6. This elegant retreat features a beautiful poolside bar, superb for sipping drinks while soaking up the sun. Guests rave about the delicious breakfast options and the attentive service, making it a favorite for families seeking both luxury and comfort. With amenities like a golf course on-site, tennis courts, and beautifully designed rooms equipped with premium bedding and rainfall showerheads, the Inn at Perry Cabin truly elevates the vacation experience.For travellers looking for a more budget-friendly option, St Michaels Inn offers a comfortable stay with an outdoor pool and a traveller rating of 8.2. Guests appreciate the friendly and helpful staff, as well as the convenient location. Enjoy a complementary breakfast before lounging by the pool or exploring the charming surroundings. This hotel is a great choice for families who want quality without breaking the bank.Another delightful option is the George Brooks House B&B, a cozy 3-star hotel featuring an outdoor pool, rated 8.6 by visitors. With its inviting atmosphere and excellent service, this B&B is superb for those seeking a quaint experience. Guests can relax on furnished balconies or patios, enjoying the serene surroundings.Lastly, for those seeking a great experience, the LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL boasts a superb rating of 10.0. This charming property features a heated pool and a fully equipped kitchen, ideal for families who want the convenience of home while enjoying a vacation.
How much does a hotel with outdoor pool in St Michaels cost?
Enjoy staying in a hotel in St Michaels with an outdoor pool. You can find a great deal from $96 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Which St Michaels hotels offer poolside service for food and drinks?
The Inn at Perry Cabin is a luxurious 5-star retreat in St. Michaels, Maryland, renowned for its exceptional service and stunning surroundings. With a remarkable traveller rating of 9.6, guests rave about the attentive staff and the beautiful location that complements the exquisite amenities.One of the standout features of the Inn at Perry Cabin is its inviting outdoor pool, where you can unwind while enjoying the convenience of poolside service for food and drinks. Imagine sipping a refreshing cocktail or indulging in a delicious snack without leaving the comfort of your sunbed. The poolside bar enhances this experience, making it a great spot for families and couples alike who appreciate quality and convenience.Beyond the pool, the Inn offers a range of luxurious amenities, including a garden-view restaurant, 24-hour room service, and beautifully appointed rooms featuring premium bedding and deep soaking bathtubs. Additionally, guests can enjoy onsite activities such as golf and tennis, ensuring an adventurous and comfortable stay for those traveling with children.
Are there hotels with outdoor pools that are close to Perry Cabin Park?
The Inn at Perry Cabin is a stunning 5-star hotel that features a beautiful outdoor pool, making it a superb choice for travellers seeking relaxation and adventure near Perry Cabin Park. Guests rave about the attentive service and luxurious amenities, which include a poolside bar, 24-hour room service, and elegant rooms with premium bedding and deep soaking bathtubs. With a stellar review rating of 9.6, it's no wonder visitors find the location beautiful and the breakfast delicious.For a more casual yet charming option, the George Brooks House B&B offers an inviting outdoor pool along with cozy, clean rooms that have furnished balconies and patios. This 3-star property provides excellent service and includes free breakfast, making it a delightful choice for families or those looking for a homey atmosphere. With a review rating of 8.6, guests appreciate the comfortable surroundings and the ease of self-parking.
Is it cheaper to book flights and a St Michaels hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in St Michaels for you.

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