Find Hotels with a Pool in St. Michaels, MD

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Check availability on St. Michaels Hotels with a Pool

Tonight
Nov 6 - Nov 7
Tomorrow
Nov 7 - Nov 8
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Top St. Michaels Hotels with a Pool

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn
St Michaels Inn
2.5 star property
  • Pool loungers
8.2 out of 10, Very Good, (1001)
Sparkling waters beckon at the seasonal outdoor pool, complete with sun loungers and umbrellas from May through September. Conveniently situated near Chesapeake Bay Maritime Museum, this hotel offers continental breakfast and garden views after invigorating local hikes.
The price is NT$3,433
NT$3,776 total
includes taxes & fees
Nov 9 - Nov 10
St Michaels Inn
Outdoor pool
Inn at Perry Cabin
Inn at Perry Cabin
5.0 star property
  • Outdoor pool
  • Poolside bar
  • Hot tub
9.6 out of 10, Exceptional, (368)
Swimming becomes an elevated experience at this waterfront sanctuary, complete with a poolside bar for refreshing cocktails. Guests relish the outdoor hot tub after exploring the 18-hole golf course, marina, or tennis courts.
The price is NT$11,922
NT$14,426 total
includes taxes & fees
Nov 17 - Nov 18
Inn at Perry Cabin
Exterior
George Brooks House B&B
George Brooks House B&B
3.0 star property
  • Outdoor pool
8.6 out of 10, Excellent, (65)
Aquatic relaxation awaits at this charming bed & breakfast's outdoor pool, surrounded by lush gardens. Mornings begin with delicious complimentary breakfast before guests explore nearby maritime museums or venture out on provided bicycles.
The price is NT$5,558
NT$6,114 total
includes taxes & fees
Nov 12 - Nov 13
George Brooks House B&B
Porch
Parsonage Inn
Parsonage Inn
3.5 star property
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
9.2 out of 10, Wonderful, (130)
Bicycles await adventurous souls ready to explore maritime treasures before cooling off at a nearby pool. Mornings begin with superb, fresh breakfasts, while evenings invite relaxation in gardens or by the lobby fireplace.
The price is NT$7,071
NT$7,778 total
includes taxes & fees
Nov 12 - Nov 13
Parsonage Inn
Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
Rod 'N' Reel Resort
Rod 'N' Reel Resort
4.0 star property
  • Indoor pool
  • Pool loungers
  • Near the beach
8.4 out of 10, Very Good, (1000)
Sparkling waters beckon at dual pools, where cabanas offer shaded luxury beside the marina. Beyond refreshing dips, guests enjoy complimentary bicycles, kayaking adventures, and nearby beach access, creating a complete coastal escape.
The price is NT$3,047
NT$4,000 total
includes taxes & fees
Nov 12 - Nov 13
Rod 'N' Reel Resort
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
  • Pool loungers
9.2 out of 10, Wonderful, (914)
Splashing in the seasonal outdoor pool reveals stunning Chesapeake Bay vistas, creating a waterfront oasis complete with sun loungers and umbrellas. Nearby adventures include hiking trails, kayaking, and sailing for the perfect coastal getaway.
The price is NT$2,934
NT$3,256 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool
Knapps Narrows Marina & Inn
Knapps Narrows Marina & Inn
3.0 star property
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (348)
Marina-side seasonal pool creates a serene retreat overlooking Chesapeake Bay waters. Guests appreciate the immaculate rooms with private balconies, complimentary bicycles for island adventures, and boat tours launching steps away.
The price is NT$3,088
NT$3,397 total
includes taxes & fees
Nov 9 - Nov 10
Knapps Narrows Marina & Inn
Indoor pool
Comfort Inn & Suites Cambridge
Comfort Inn & Suites Cambridge
2.5 star property
  • Indoor pool
8.2 out of 10, Very Good, (780)
Swimming enthusiasts delight in the temperature-controlled indoor pool, open from 9:00 AM to 10:00 PM daily. Beyond aquatic recreation, guests appreciate free bicycles for exploring nearby Choptank River Lighthouse and the consistently praised breakfast buffet.
The price is NT$3,386
NT$3,758 total
includes taxes & fees
Dec 7 - Dec 8
Comfort Inn & Suites Cambridge
Exterior
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
  • Full-service spa
9.4 out of 10, Exceptional, (425)
Seasonal outdoor pool beckons from May to September amid upscale amenities at this Chesapeake Bay hotel. Professional staff complement the experience with nearby dining options, complimentary bicycles, and rejuvenating spa treatments.
The price is NT$5,713
NT$7,127 total
includes taxes & fees
Dec 7 - Dec 8
The Inn at Chesapeake Bay Beach Club
Seasonal outdoor pool
Wylder Tilghman Island
Wylder Tilghman Island
2.0 star property
  • On private beach
8.8 out of 10, Excellent, (88)
Seasonal outdoor swimming beckons travelers from March through October at this waterfront haven. Complementing the pool, a private beach, sauna, and free bicycles create perfect relaxation opportunities along the river's edge.
The price is NT$4,684
NT$6,513 total
includes taxes & fees
Dec 1 - Dec 2
Wylder Tilghman Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top St. Michaels Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Staff was very friendly answering all questions, room was clean and very comfortable bed"
Frances 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD

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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 free self parking, an outdoor pool, and complimentary wireless internet access. George Brooks House B&B: Offers kitchens, a communal pool, and televisions. Parsonage Inn: Provides 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 St. Michaels Museum 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.