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
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for St. Michaels hotels with a pool

A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern bar area with a long counter and multiple bar stools.

1. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
  • Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
$132 nightly
$146 total
Oct 27 - Oct 28
Total with taxes and fees
Rod 'N' Reel Resort
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 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.

2. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$81 nightly
$89 total
Nov 17 - Nov 18
Total with taxes and fees
St Michaels Inn
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 white house with a garden patio featuring a wicker chair and a round table.
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.
$513 nightly
$564 total
Nov 11 - Nov 12
Total with taxes and fees
Inn at Perry Cabin
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 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.
$215 nightly
$237 total
Nov 2 - Nov 3
Total with taxes and fees
George Brooks House B&B
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

5. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
$489 nightly
$538 total
Oct 18 - Oct 19
Total with taxes and fees
The Oaks Waterfront
A rectangular pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A restaurant with wooden tables and chairs, a bar area, and a tiled floor.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

6. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
$111 nightly
$126 total
Oct 20 - Oct 21
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A multi-story hotel with a brick facade, large windows, and an American flag.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

7. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
  • Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.
$106 nightly
$121 total
Nov 15 - Nov 16
Total with taxes and fees
Crowne Plaza Annapolis by IHG
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
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 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.
$119 nightly
$131 total
Nov 15 - Nov 16
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A waterfront hotel with a covered dock and a large building with multiple balconies.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.
A waterfront property with a covered patio, a dock, and a boat.

9. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
$228 nightly
$250 total
Oct 18 - Oct 19
Total with taxes and fees
Wylder Tilghman Island
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

10. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Aquatic paradise awaits with 2 outdoor pools, indoor pool, and waterslide offering year-round relaxation at this riverside resort.
$215 nightly
$244 total
Nov 10 - Nov 11
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean room, very nice decor and great staff"
Nadine 2-night trip
Posted 1 day ago
Graduate by Hilton Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 1 day ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 6 days ago
Sonesta ES Suites 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 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 $89 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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