Plan your trip
Photo by Louise Johnson
Check prices for these dates, December 14 – 15, 2026
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.
Breakfast included
Hot tub
4 stars
Spa
5 stars
St. Michaels, a charming waterfront town, offers a delightful blend of history, culture, and outdoor activities that will captivate any traveler. Start your exploration at the fascinating maritime museum, where you can delve into the region's rich nautical heritage through engaging exhibits and artifacts that bring the area's seafaring past to life. For those seeking adventure, a scenic bike ride along the picturesque shoreline reveals stunning views of the Chesapeake Bay, ideal for family outings. Art enthusiasts will appreciate the local galleries showcasing both contemporary and traditional works, providing a perfect opportunity to find unique souvenirs. Don’t miss the chance to sample local delicacies at farmers' markets, where you can taste fresh produce and artisanal goods, supporting the community while indulging in delicious flavors. Finally, enjoy a leisurely stroll through the beautifully preserved historic district, with its charming architecture and inviting shops, creating a perfect backdrop for a relaxing afternoon. With a variety of high-quality accommodations nearby, you can unwind in comfort after a day of exploration, ensuring a memorable stay in this picturesque town.
For travelers seeking a refreshing getaway in St. Michaels, these hotels offer inviting pool amenities that promise relaxation and enjoyment during your stay.
The Inn at Perry Cabin is a stunning 5-star hotel that offers an exceptional outdoor pool experience, rated highly by guests with an impressive score of 9.6. This elegant retreat features a beautiful poolside bar, superb for sipping drinks while soaking up the sun. Guests rave about the delicious breakfast options and the attentive service, making it a favorite for families seeking both luxury and comfort. With amenities like a golf course on-site, tennis courts, and beautifully designed rooms equipped with premium bedding and rainfall showerheads, the Inn at Perry Cabin truly elevates the vacation experience.
For travellers looking for a more budget-friendly option, St Michaels Inn offers a comfortable stay with an outdoor pool and a traveller rating of 8.2. Guests appreciate the friendly and helpful staff, as well as the convenient location. Enjoy a complementary breakfast before lounging by the pool or exploring the charming surroundings. This hotel is a great choice for families who want quality without breaking the bank.
Another delightful option is the George Brooks House B&B, a cozy 3-star hotel featuring an outdoor pool, rated 8.6 by visitors. With its inviting atmosphere and excellent service, this B&B is superb for those seeking a quaint experience. Guests can relax on furnished balconies or patios, enjoying the serene surroundings.
Lastly, for those seeking a great experience, the LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL boasts a superb rating of 10.0. This charming property features a heated pool and a fully equipped kitchen, ideal for families who want the convenience of home while enjoying a vacation.
Enjoy staying in a hotel in St Michaels with an outdoor pool. You can find a great deal from $101 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.
The Inn at Perry Cabin is a luxurious 5-star retreat in St. Michaels, Maryland, renowned for its exceptional service and stunning surroundings. With a remarkable traveller rating of 9.6, guests rave about the attentive staff and the beautiful location that complements the exquisite amenities.
One of the standout features of the Inn at Perry Cabin is its inviting outdoor pool, where you can unwind while enjoying the convenience of poolside service for food and drinks. Imagine sipping a refreshing cocktail or indulging in a delicious snack without leaving the comfort of your sunbed. The poolside bar enhances this experience, making it a great spot for families and couples alike who appreciate quality and convenience.
Beyond the pool, the Inn offers a range of luxurious amenities, including a garden-view restaurant, 24-hour room service, and beautifully appointed rooms featuring premium bedding and deep soaking bathtubs. Additionally, guests can enjoy onsite activities such as golf and tennis, ensuring an adventurous and comfortable stay for those traveling with children.
The Inn at Perry Cabin is a stunning 5-star hotel that features a beautiful outdoor pool, making it a superb choice for travellers seeking relaxation and adventure near Perry Cabin Park. Guests rave about the attentive service and luxurious amenities, which include a poolside bar, 24-hour room service, and elegant rooms with premium bedding and deep soaking bathtubs. With a stellar review rating of 9.6, it's no wonder visitors find the location beautiful and the breakfast delicious.
For a more casual yet charming option, the George Brooks House B&B offers an inviting outdoor pool along with cozy, clean rooms that have furnished balconies and patios. This 3-star property provides excellent service and includes free breakfast, making it a delightful choice for families or those looking for a homey atmosphere. With a review rating of 8.6, guests appreciate the comfortable surroundings and the ease of self-parking.
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 vacation package.
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 in St Michaels for you.