St. Michaels Hotel Guide - Hotels with Pool in St. Michaels, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on St. Michaels Hotels with Pool

Our top choices for 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
8.2 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is €127
includes taxes & fees
20 Apr - 21 Apr
St Michaels Inn
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (71 reviews)
  • cleanliness
    Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
The price is €145
includes taxes & fees
15 Apr - 16 Apr
George Brooks House B&B
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
  • cleanliness
    Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons.
The price is €188
includes taxes & fees
16 Apr - 17 Apr
Parsonage Inn
Outdoor pool

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (380 reviews)
  • cleanliness
    Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
The price is €566
includes taxes & fees
5 May - 6 May
Inn at Perry Cabin
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is €131
includes taxes & fees
15 Apr - 16 Apr
Kent Island Resort
Outdoor pool

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (480 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is €148
includes taxes & fees
14 Apr - 15 Apr
Anchored Inn at Hidden Harbour Marina
Indoor pool

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
The price is €102
includes taxes & fees
14 Apr - 15 Apr
Best Western Plus Easton Inn & Suites
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (379 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is €141
includes taxes & fees
14 Apr - 15 Apr
Knapps Narrows Marina & Inn
Seasonal outdoor pool

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
  • cleanliness
    Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
The price is €152
includes taxes & fees
27 Apr - 28 Apr
Wylder Tilghman Island
Outdoor pool, pool loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is €133
includes taxes & fees
18 Apr - 19 Apr
Inn at Huntingfield Creek
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.
View all properties

Choose what matters most at hotels with a pool in St. Michaels

Breakfast included
Hot tub

Top St. Michaels Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

4/10 Poor
"the room was disgusting and in the basement. the front desk was rude and dismissive about our wanting to move. everything is old and smells like mold"
alicia 2-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some accommodation options with pools in St. Michaels?
Inn at Perry Cabin: Features a full-service spa, an outdoor pool and 2 bars. St Michaels Inn: Offers daily, a seasonal outdoor pool and free self parking. The Wildset: Features free self parking, an outdoor pool and complimentary wireless Internet access. George Brooks House B&B: Features complimentary wireless Internet access, a pool and kitchens. 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.