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 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
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
Nov 10 - Nov 11
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 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.
$80 nightly
$88 total
Nov 22 - Nov 23
Total with taxes and fees
St Michaels Inn
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 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.

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.
$485 nightly
$533 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 two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.

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.
$199 nightly
$219 total
Oct 25 - Oct 26
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 25 - Oct 26
Total with taxes and fees
The Oaks Waterfront
A rectangular pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
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.

6. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
$91 nightly
$104 total
Nov 22 - Nov 23
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A modern living room with a fireplace, two armchairs, a coffee table, and decorative items.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A multi-story hotel with a brick facade, large windows, and an American flag.

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.
$103 nightly
$117 total
Nov 22 - Nov 23
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 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.
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 view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.

9. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
$250 nightly
$275 total
Oct 25 - Oct 26
Total with taxes and fees
Wylder Tilghman Island
A resort with a large pool, outdoor seating, and a view of the sea.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious lobby with a bar area, multiple seating arrangements, and a grand staircase.

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.
$169 nightly
$192 total
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Regency Chesapeake Bay
View all properties

Choose what matters most at hotels with a pool in St. Michaels

Breakfast included
Hot tub
4 stars
Spa
5 stars

Find out more about St. Michaels

Discover top St. Michaels attractions

St. Michaels, a charming waterfront town, offers a delightful blend of history, culture, and outdoor activities that will captivate any traveler. Start your exploration at the fascinating maritime museum, where you can delve into the region's rich nautical heritage through engaging exhibits and artifacts that bring the area's seafaring past to life. For those seeking adventure, a scenic bike ride along the picturesque shoreline reveals stunning views of the Chesapeake Bay, ideal for family outings. Art enthusiasts will appreciate the local galleries showcasing both contemporary and traditional works, providing a perfect opportunity to find unique souvenirs. Don’t miss the chance to sample local delicacies at farmers' markets, where you can taste fresh produce and artisanal goods, supporting the community while indulging in delicious flavors. Finally, enjoy a leisurely stroll through the beautifully preserved historic district, with its charming architecture and inviting shops, creating a perfect backdrop for a relaxing afternoon. With a variety of high-quality accommodations nearby, you can unwind in comfort after a day of exploration, ensuring a memorable stay in this picturesque town.

Find the best pool hotels in St. Michaels

For travelers seeking a refreshing getaway in St. Michaels, these hotels offer inviting pool amenities that promise relaxation and enjoyment during your stay.

Inn at Perry Cabin

  • Why it's great: For an unparalleled experience centered around luxurious poolside relaxation, the Inn at Perry Cabin stands out as a top choice. This 5-star hotel has earned a perfect traveler review rating of 10 out of 10, thanks to its stunning outdoor pool and poolside bar, where travelers can unwind in style while enjoying picturesque waterfront views.
  • Other amenities: The hotel features a full-service spa offering a range of treatments, including aromatherapy and facials, ensuring travelers can indulge in complete rejuvenation. Guests can also enjoy premium bedding in elegantly designed rooms, a cozy fireplace, and an onsite restaurant with ocean views. Additional conveniences include 24-hour room service, free Wi-Fi, and a golf course on-site. With a marina nearby and outdoor tennis available, there's plenty to explore for active travelers.
  • Neighborhood: Downtown St. Michaels
  • Nearby attractions: Perry Cabin Park - less than 1 mile, Clint S. Bradley Park - less than 1 mile

George Brooks House B&B

  • Why it's great: The George Brooks House B&B offers a charming retreat with its inviting outdoor pool, perfect for leisurely afternoons in St. Michaels. This 3-star hotel boasts an excellent review rating of 9 out of 10, making it a delightful choice for travelers seeking a cozy atmosphere with poolside access.
  • Other amenities: Guests can enjoy complimentary breakfast each day, along with daily housekeeping services to ensure a comfortable stay. The hotel features beautifully designed rooms with premium bedding and a fireplace for added warmth. Visitors can relax on the terrace or in the garden, and amenities such as Wi-Fi and self-parking further enhance the convenience of this lovely B&B.
  • Nearby attractions: Perry Cabin Park - less than 1 mile, Higgins Yacht Yard and Marina - 1 mile, Saint Marys Square Museum - 1 mile

St Michaels Inn

  • Why it's great: The St Michaels Inn is a budget-friendly gem that caters to pool enthusiasts looking for a laid-back atmosphere. With a solid review rating of 8 out of 10, this hotel features a secure shared pool equipped with sun loungers and umbrellas, providing the perfect spot to soak up the sun.
  • Other amenities: Guests can enjoy complimentary continental breakfast each morning, along with free Wi-Fi and self-parking for added convenience. The hotel's location in the historical district makes it an ideal base for exploring nearby attractions. Additional features include a garden, a terrace for relaxation, and cribs available for families traveling with infants.
  • Nearby attractions: Saint Michaels Village - less than 1 mile, Classic Motor Museum - 1 mile

Top St. Michaels Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Great last minute booking. All went smoothly"
Kelly 1-night trip
Posted 23 hours ago
The Westin Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."
William 1-night trip
Posted 1 day ago
Rod 'N' Reel Resort
Best Western Annapolis

Best Western Annapolis

8/10 Good
"If you want to get a feel for Annapolis, you should try a hotel closer to the harbor. Since we had seen Annapolis many times and were looking for a quick, efficient stay, this met our needs. A few remarks on the property; - Needs updates -bathroom door did not close fully - mystery eggs were part of breakfast, but coffee was good."
David 1-night trip
Posted 1 day ago
Best Western Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"older facility but kept clean. a good value for an over night"
John 1-night trip
Posted 1 day ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Very pleasant surprise! Great price for studio apartment- way better than the Marriott I just checked out of!"
Rhonda 1-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"It’s a hotel that is a bit worn but the rooms are great and the staff is very polite. I’ll definitely be back."
Richard 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD

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 $88 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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