Find Hotels with a Pool in St. Michaels, MD from CA $128

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Our top choices for St. Michaels hotels with a pool

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
St Michaels Inn

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (131 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 CA $203
CA $224 total
includes taxes & fees
Mar 2 - Mar 3
Parsonage Inn

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (67 reviews)
  • cleanliness
    Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
The price is CA $231
CA $254 total
includes taxes & fees
Mar 2 - Mar 3
George Brooks House B&B

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
  • cleanliness
    Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
The price is CA $505
CA $556 total
includes taxes & fees
Mar 4 - Mar 5
Inn at Perry Cabin

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (370 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is CA $136
CA $150 total
includes taxes & fees
Mar 1 - Mar 2
Knapps Narrows Marina & Inn

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (476 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is CA $205
CA $234 total
includes taxes & fees
Mar 1 - Mar 2
Anchored Inn at Hidden Harbour Marina

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (123 reviews)
  • cleanliness
    Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
The price is CA $218
CA $240 total
includes taxes & fees
Mar 1 - Mar 2
The Tilghman Island Inn

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
  • cleanliness
    Waterfront paradise beckons with a heated outdoor pool, private aquatic oasis, and scenic creek views in tranquil Annapolis.
The price is CA $282
CA $561 total
includes taxes & fees
Mar 1 - Mar 2
Waterfront Oasis of Annapolis Star

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (964 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is CA $143
CA $159 total
includes taxes & fees
Mar 10 - Mar 11
Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
The price is CA $155
CA $173 total
includes taxes & fees
Mar 5 - Mar 6
Hilton Garden Inn Kent Island Marina
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

Frequently asked questions

What are the best hotels in St Michaels with outdoor pools?
The Inn at Perry Cabin, a stunning 5-star hotel, stands out as a premier choice for travellers seeking luxury and relaxation in St. Michaels. With an outstanding score of 9.6, guests rave about its exquisite amenities, including a beautiful outdoor pool complemented by a poolside bar, great for sipping refreshing drinks on sunny days. The hotel also offers a serene garden-view restaurant, 24-hour room service, and a range of recreational options, including onsite tennis and a golf course, making it an ideal retreat for families and couples alike.

For those looking for a more budget-friendly option, the St. Michaels Inn is a solid choice with a friendly setting. Rated 8.2, this hotel features a pleasant outdoor pool area with sun loungers, and guests appreciate the complimentary continental breakfast that starts their day off right. The friendly staff and comfortable, clean rooms create a convenient and enjoyable stay for families.

If you're in the mood for a cozy bed and breakfast experience, the George Brooks House B&B offers a charming outdoor pool along with a terrace and balcony for relaxation. With a review score of 8.6, visitors enjoy the clean, cozy rooms and excellent service, making it a delightful option for those seeking a more intimate setting.

Lastly, for a truly great experience, consider the Luxury Coastal Farmhouse Waterfront with a heated pool. With a great rating of 10.0, this property features a spacious kitchen and inviting outdoor areas, making it a fantastic choice for families looking for a home-away-from-home experience while enjoying all the comforts of a luxury stay.
How much does a hotel with outdoor pool in St Michaels cost?
Enjoy staying in a hotel in St Michaels with an outdoor pool. You can find a great deal from CA $128 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Which St Michaels hotels offer poolside service for food and drinks?
The Inn at Perry Cabin is a luxurious 5-star hotel located in the heart of St. Michaels, Maryland, offering an exquisite poolside experience with dedicated service for food and drinks. Guests rave about the delightful poolside bar, which enhances the tranquility of the outdoor pool area, allowing families to relax while enjoying refreshments right by the water.

With a remarkable traveller rating of 9.6, the Inn at Perry Cabin is not just about the pool; it boasts beautifully appointed rooms featuring premium bedding, deep soaking bathtubs, and rainfall showerheads, ensuring a serene retreat after a day of adventure. Families can take advantage of the onsite tennis courts and picturesque gardens, making it a superb spot for both relaxation and recreation.

This hotel is well-loved for its attentive staff and delicious breakfast, adding to the overall experience of this charming getaway.
Is it cheaper to book flights and a hotel in St Michaels as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
How can I save on a hotel in St Michaels with Expedia?
Before booking your St Michaels hotel, remember to join Expedia's free travel rewards program—One Key™. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with an outdoor pool in St Michaels for you.

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