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

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

2.5 star property
St. Michaels
  • Pool loungers
8.2 out of 10, Very Good, (1002)
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 AED 376
AED 413 total
includes taxes & fees
15 Dec - 16 Dec
St Michaels Inn
Exterior
George Brooks House B&B

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 AED 661
AED 727 total
includes taxes & fees
17 Nov - 18 Nov
George Brooks House B&B
Outdoor pool
Inn at Perry Cabin

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 AED 1,769
AED 2,140 total
includes taxes & fees
11 Dec - 12 Dec
Inn at Perry Cabin
Porch
Parsonage Inn

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, (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 AED 841
AED 925 total
includes taxes & fees
10 Dec - 11 Dec
Parsonage Inn
Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
Rod 'N' Reel Resort

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 AED 362
AED 476 total
includes taxes & fees
23 Nov - 24 Nov
Rod 'N' Reel Resort
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4.0 star property
Cambridge
  • 2 outdoor pools
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On private beach
  • Hot tub
8.8 out of 10, Excellent, (1000)
Splash down the waterslide into aquatic bliss at this riverside resort's multiple pools. Guests enjoy poolside dining, a hot tub retreat, and sun loungers for ultimate relaxation, all complemented by golf, tennis, and spa treatments nearby.
The price is AED 614
AED 796 total
includes taxes & fees
15 Dec - 16 Dec
Hyatt Regency Chesapeake Bay
Seasonal outdoor pool
Knapps Narrows Marina & Inn

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, (352)
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 AED 367
AED 404 total
includes taxes & fees
24 Nov - 25 Nov
Knapps Narrows Marina & Inn
Indoor pool
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 star property
Cambridge
  • Indoor pool
8.2 out of 10, Very Good, (785)
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 AED 403
AED 447 total
includes taxes & fees
2 Dec - 3 Dec
Comfort Inn & Suites Cambridge
Exterior
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
  • Full-service spa
9.4 out of 10, Exceptional, (426)
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 AED 675
AED 843 total
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
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
Grasonville
  • Pool loungers
9.2 out of 10, Wonderful, (919)
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 AED 393
AED 436 total
includes taxes & fees
19 Nov - 20 Nov
Holiday Inn Express Annapolis East-Kent Island 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.
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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
"Wonderful country inn!"
Jennifer 4-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. John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!: 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.