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

Find Hotels with a Pool in St. Michaels, MD from CA $114

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Check availability on St. Michaels Hotels with a Pool

Tonight
Oct 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 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.

1. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
CA $104
CA $114 total
includes taxes & fees
Nov 22 - Nov 23
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.

2. 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.
CA $681
CA $749 total
includes taxes & fees
Nov 11 - Nov 12
Inn at Perry Cabin
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.

3. 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.
CA $351
CA $386 total
includes taxes & fees
Nov 2 - Nov 3
Parsonage 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.

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.
CA $272
CA $299 total
includes taxes & fees
Nov 2 - Nov 3
George Brooks House B&B
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A large building with a swimming pool, dock, and green surroundings.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
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.
CA $246
CA $270 total
includes taxes & fees
Oct 25 - Oct 26
The Tilghman Island Inn
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 covered patio area with wicker furniture and a view of a building with large windows.
A waterfront property with houses, a dock, and a grassy area.

6. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
CA $183
CA $201 total
includes taxes & fees
Oct 31 - Nov 1
Knapps Narrows Marina & Inn
A swimming pool with a white fence, lounge chairs, and umbrellas.
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.
Two Adirondack chairs facing a calm body of water with a clear sky above.

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.
CA $139
CA $154 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express Annapolis East-Kent Island 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 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.

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.
CA $167
CA $184 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Plus Easton Inn & Suites
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 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.

9. 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.
CA $190
CA $209 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Easton
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A hotel hallway with carpeted floors, white doors, and overhead lighting.
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.

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.
CA $180
CA $198 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Inn Easton
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

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 13 hours ago
Sonesta ES Suites Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Staff was very pleasant. Room was clean and a very nice Breakfast included."
Dean 1-night trip
Posted 16 hours ago
St Michaels Inn
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"We stayed for two nights and were very happy with the size and quality of the room. The buffet-Breakfast was excellent and included in the rate. A large shopping mall and several restaurants nearby."
JONATHAN 2-night trip
Posted 21 hours ago
Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Esperaba mas de este hotel. Aun asi no esta mal."
Christian 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis
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 3 days ago
Best Western Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Loved the balcony."
Hildehardo F 4-night trip
Posted 3 days ago
Rod 'N' Reel Resort

Frequently asked questions

What are the best hotels in St Michaels with outdoor pools?
The Inn at Perry Cabin, a stunning 5-star hotel, stands out as a premier choice for travellers seeking luxury and relaxation in St. Michaels. With an outstanding score of 9.6, guests rave about its exquisite amenities, including a beautiful outdoor pool complemented by a poolside bar, great for sipping refreshing drinks on sunny days. The hotel also offers a serene garden-view restaurant, 24-hour room service, and a range of recreational options, including onsite tennis and a golf course, making it an ideal retreat for families and couples alike.For those looking for a more budget-friendly option, the St. Michaels Inn is a solid choice with a friendly setting. Rated 8.2, this hotel features a pleasant outdoor pool area with sun loungers, and guests appreciate the complimentary continental breakfast that starts their day off right. The friendly staff and comfortable, clean rooms create a convenient and enjoyable stay for families.If you're in the mood for a cozy bed and breakfast experience, the George Brooks House B&B offers a charming outdoor pool along with a terrace and balcony for relaxation. With a review score of 8.6, visitors enjoy the clean, cozy rooms and excellent service, making it a delightful option for those seeking a more intimate setting.Lastly, for a truly great experience, consider the Luxury Coastal Farmhouse Waterfront with a heated pool. With a great rating of 10.0, this property features a spacious kitchen and inviting outdoor areas, making it a fantastic choice for families looking for a home-away-from-home experience while enjoying all the comforts of a luxury stay.
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 CA $114 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 hotel located in the heart of St. Michaels, Maryland, offering an exquisite poolside experience with dedicated service for food and drinks. Guests rave about the delightful poolside bar, which enhances the tranquility of the outdoor pool area, allowing families to relax while enjoying refreshments right by the water.With a remarkable traveller rating of 9.6, the Inn at Perry Cabin is not just about the pool; it boasts beautifully appointed rooms featuring premium bedding, deep soaking bathtubs, and rainfall showerheads, ensuring a serene retreat after a day of adventure. Families can take advantage of the onsite tennis courts and picturesque gardens, making it a superb spot for both relaxation and recreation.This hotel is well-loved for its attentive staff and delicious breakfast, adding to the overall experience of this charming getaway.
Is it cheaper to book flights and a hotel in St Michaels 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 travel 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 with an outdoor pool in St Michaels for you.
How can I save on a hotel in St. Michaels with Expedia?
Before booking your St. Michaels hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access instant discounts with Member Prices as well as member-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

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