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
25 Aug - 26 Aug
Tomorrow
26 Aug - 27 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for St. Michaels hotels with a pool

1. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
SAR 304
SAR 335 total
includes taxes & fees
31 Aug - 1 Sep
St Michaels Inn

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.
SAR 1,597
SAR 1,757 total
includes taxes & fees
7 Sep - 8 Sep
Inn at Perry Cabin

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.
SAR 794
SAR 874 total
includes taxes & fees
26 Aug - 27 Aug
George Brooks House B&B

4. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
SAR 563
SAR 620 total
includes taxes & fees
26 Aug - 27 Aug
Knapps Narrows Marina & Inn

5. 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.
SAR 522
SAR 574 total
includes taxes & fees
30 Aug - 31 Aug
Best Western Plus Easton Inn & Suites

6. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
SAR 770
SAR 847 total
includes taxes & fees
26 Aug - 27 Aug
The Tilghman Island Inn

7. Quality Inn

Quality Inn
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.
SAR 389
SAR 428 total
includes taxes & fees
27 Aug - 28 Aug
Quality Inn

8. 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.
SAR 477
SAR 529 total
includes taxes & fees
1 Sep - 2 Sep
Holiday Inn Express Annapolis East-Kent Island by IHG

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.
SAR 507
SAR 558 total
includes taxes & fees
30 Aug - 31 Aug
Fairfield Inn & Suites by Marriott Easton

10. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
SAR 446
SAR 495 total
includes taxes & fees
31 Aug - 1 Sep
Best Western Kent Narrows 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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The staff were kind and welcoming. Wonderful experience!"
Kimberly 1-night trip
Posted 4 hours ago
Rod 'N' Reel Resort
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

8/10 Good
"I wish I could give half stars because this place is really a 4.5 stars. First off this place was great, it is everything you need for a hotel. Great prices, friendly staff, very clean, very nice hotel. Why I gave it 4 stars? The coffee machine was down for our first night, the jacuzzi was down for maintenance, the wifi went for maintenance lol so it was a little much but I know you can't always control those things. Another small thing, I also wish the TV's were smart TV's and I wish the rooms came with a microwave. Overall great hotel, would stay here again."
Joseph 3-night trip
Posted 4 hours ago
Crowne Plaza Annapolis by IHG
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Room was clean, staff was great. They should have notified in advance or had on line about all the construction and pool being closed."
Rick 1-night trip
Posted 9 hours ago
St Michaels Inn
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good
"There wasn’t a fan in the bathroom. Very good location in Annapolis."
Tracie 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean room and staff was very courteous."
Daetonya 1-night trip
Posted 2 days ago
Courtyard by Marriott 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 4 days ago
George Brooks House B&B

Frequently asked questions

What are some accommodations 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 kitchens, a communal pool, and televisions. St. Michaels Escape | Pool, Hot Tub & Fire Pit: Offers free self parking, an outdoor pool, and complimentary wireless internet access. George Brooks House B&B: Offers kitchens, a communal pool, and televisions.
What is there to see and do in St. Michaels?
Make a point to visit attractions like Church Cove Park and Chesapeake Bay Maritime Museum. Discover sights such as St. Michaels Marina, St. Michaels Winery, and Saint Michaels Village 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 an accommodation with an outdoor swimming pool if you plan to visit St. Michaels in the warmest months of July, August, or June when the average temperature is 75°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 41°F.