Find Hotels with a Pool in St. Michaels, MD

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Check availability on St. Michaels Hotels with a Pool

Top St. Michaels Hotels with a Pool

St Michaels Inn

2.5 star property
St. Michaels
  • Pool loungers
8.2 out of 10, Very Good, (1000)
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$3,465
NT$3,811 total
includes taxes & fees
Nov 23 - Nov 24
St Michaels Inn

Inn at Perry Cabin

5.0 star property
St. Michaels
  • Outdoor pool
  • Poolside bar
  • Hot tub
9.6 out of 10, Exceptional, (369)
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$13,339
NT$16,140 total
includes taxes & fees
Dec 4 - Dec 5
Inn at Perry Cabin

George Brooks House B&B

3.0 star property
St. Michaels
  • 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$5,610
NT$6,171 total
includes taxes & fees
Nov 20 - Nov 21
George Brooks House B&B

Parsonage Inn

3.5 star property
St. Michaels
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
9.2 out of 10, Wonderful, (131)
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$7,137
NT$7,851 total
includes taxes & fees
Nov 20 - Nov 21
Parsonage Inn

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
  • 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$2,814
NT$3,747 total
includes taxes & fees
Nov 20 - Nov 21
Rod 'N' Reel Resort

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (355)
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$3,117
NT$3,428 total
includes taxes & fees
Nov 23 - Nov 24
Knapps Narrows Marina & Inn

Wylder Tilghman Island

2.0 star property
Tilghman
  • 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$4,341
NT$6,146 total
includes taxes & fees
Dec 2 - Dec 3
Wylder Tilghman Island

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
  • Full-service spa
9.4 out of 10, Exceptional, (427)
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$5,730
NT$7,153 total
includes taxes & fees
Dec 1 - Dec 2
The Inn at Chesapeake Bay Beach Club

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1000)
Waterfront serenity awaits at the indoor pool, complete with comfortable sun loungers and extended hours from 5 AM to 11 PM. Steps from the marina, this hotel combines aquatic pleasure with scenic beauty and a modern fitness center.
The price is NT$2,972
NT$3,299 total
includes taxes & fees
Nov 25 - Nov 26
Hilton Garden Inn Kent Island Marina

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
  • Indoor pool
8.8 out of 10, Excellent, (1004)
Swimming enthusiasts revel in the refreshing indoor pool at this Annapolis hotel, complemented by a 24-hour fitness center. Positioned near Westfield Annapolis Mall, guests appreciate the convenient restaurant, bar, and thoughtful amenities like free parking.
The price is NT$2,902
NT$3,308 total
includes taxes & fees
Dec 7 - Dec 8
Crowne Plaza Annapolis by IHG
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.

Top St. Michaels Hotel Reviews

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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 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.