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

Hotels with Swimming Pools in St. Michaels

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Check availability on St. Michaels Hotels with Swimming Pools

Tonight
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

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.
S$118
includes taxes & fees
31 Aug - 1 Sept
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.
S$595
includes taxes & fees
7 Sept - 8 Sept
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.
S$296
includes taxes & fees
14 Sept - 15 Sept
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.
S$210
includes taxes & fees
26 Aug - 27 Aug
Knapps Narrows Marina & Inn

5. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
S$315
includes taxes & fees
31 Aug - 1 Sept
The Tilghman Island Inn

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.
S$194
includes taxes & fees
23 Aug - 24 Aug
Best Western Plus Easton Inn & Suites

7. Quality Inn

Quality Inn
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
S$158
includes taxes & fees
23 Aug - 24 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.
S$179
includes taxes & fees
7 Sept - 8 Sept
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.
S$189
includes taxes & fees
13 Sept - 14 Sept
Fairfield Inn & Suites by Marriott Easton

10. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
  • Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
S$142
includes taxes & fees
14 Sept - 15 Sept
Quality Inn Grasonville near Kent Island
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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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 4 hours ago
Crowne Plaza Annapolis by IHG
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf course. Families can be quite boisterous; we will opt for calmer winter months in future."
Annette 2-night trip
Posted 14 hours ago
Hyatt Regency Chesapeake Bay
St Michaels Inn

St Michaels Inn

8/10 Good
"Property was a bit outdated but hopefully the construction will give it the update it needs."
David 2-night trip
Posted 16 hours ago
St Michaels Inn
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 17 hours ago
George Brooks House B&B
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean and comfortable room, helpful staff and great room service!"
Catherine 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Perfectly decent hotel for overnight stay during roadtrip."
Phyllis 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Amazing experience highly recommend"
Andrew 2-night trip
Posted 5 days ago
Inn at Perry Cabin
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Breakfast bacon was inedible, but breakfast otherwise substantial."
Maureen 1-night trip
Posted 6 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some accommodation options 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. George Brooks House B&B: Offers free self parking, an outdoor pool and complimentary wireless Internet access. Parsonage Inn: Offers kitchens, a communal pool and televisions.
What is there to see and do in St. Michaels?
Make a point to visit attractions such as 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 accommodation that has an outdoor pool if you'll be visiting St. Michaels in the warmest months of July, August or June, when the average temperature is 24°C. Accommodation with an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temp is 5°C.

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