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.
St. Michaels, Maryland, is a charming waterfront town perfect for quality-seeking travelers. Start your journey at the Chesapeake Bay Maritime Museum, where you can explore the region's rich maritime history through engaging exhibits and historic vessels. For an outdoor adventure, take a scenic bike ride along the picturesque St. Michaels Nature Trail, where the stunning views of the bay and lush landscapes await. Don't miss the chance to indulge in locally-sourced seafood at one of the waterfront restaurants, such as The Crab Claw, known for its mouthwatering crab cakes and stunning sunset views. Families with children will love the interactive experiences at the St. Michaels Museum, where you can learn about local history in a fun and engaging way. Finally, unwind with a relaxing afternoon at the St. Michaels Winery, where you can sample exquisite wines while soaking in the serene vineyard surroundings. For accommodations, consider staying in the historic district, where charming inns and boutique hotels provide a cozy yet luxurious feel, complete with attentive service to ensure your every need is met during your stay.
With a patio, shopping and other conveniences, Charming St Michaels Home is perfect for your extended stay in St. Michaels. Another excellent pick is Riverview Retreat - Charming Waterfront Cottage In St Michaels. Book a stay here and make use of a barbecue grill, a yard and more. Both long-term hotels also have a kitchenette or kitchen where you can serve up your favorite dishes. Use the cash you save on costly takeouts for exciting things like visiting popular sights.
Grab your bags, and your canine companion, and get comfy at Dollhouse In Central Historic St Michaels. This extended stay in St. Michaels makes pets and their owners feel welcome with pet-friendly services, a garden and other helpful amenities. W Melson House is another long-term stay your pup will love as much as you. It features pet-friendly services, a garden and more.
For an extended escape in St. Michaels, it's tough to beat the downtown area. And that's exactly where you'll find Riverview Retreat - Charming Waterfront Cottage In St Michaels. Offering a barbecue grill and a yard, it's the perfect base to explore this destination at your own pace. Also consider Captain's Cove - Fantastic Family Compound Just 1. Fitness facilities and a swimming pool are among the handy amenities at this extended stay hotel. Once you've unpacked and made yourself at home, it's time to see the sights. Need some inspo? We think you'll love St. Michaels Winery and Chesapeake Bay Maritime Museum.
When you're traveling for a while with the family, eating out all the time can be stressful — not to mention expensive. That's why it's a great idea to pick long-term stays fitted with a kitchen, like W Melson House. It offers a selection of features that make vacationing with your brood more comfortable, including pet-friendly facilities and animal viewing activities. Charming St Michaels Home can also help you save a tidy sum on restaurant bills. Cook your favorite meals and enjoy this property's amenities, such as animal viewing activities and cycling.
Nothing says fun like a pool does. Slip on your board shorts or bikini and splash around at Dollhouse In Central Historic St Michaels. A kitchen, a queen bed and a dryer are some of the amenities here. Another great option for your extended stay in St. Michaels is W Melson House. Your gang won't want to get out of the pool at this getaway, which also offers an oven, a barbecue grill and a kitchen so you can cook your own meals.
St. Michaels has a humid subtropical climate and temperatures range between 69 ºF and 82 ºF in summer. If you want to spend the bulk of your break kicking back by the water, this would be a fabulous time to visit.
If you're in charge of organizing an extended break with the family or your travel buddies, you'll need plenty of space. Featuring two bedrooms, Dollhouse In Central Historic St Michaels is an ideal choice. Conveniences such as a kitchen, a washing machine and a swimming pool make it a cinch to hang around for a while here. Also check out W Melson House. One of our top long-term stays in St. Michaels, this two-bedroom option offers shopping, a washing machine and more.
If you need a long-term rental for your extended stay in St. Michaels, Expedia's got you covered. Tailor your search results by amenities, location and price to find your ideal long-term stay. Some of these sought-after properties may even offer discounted weekly rates. Want to know how to snag the best deals? Sign up to become an Expedia member for free and save loads of cash with exclusive offers — plus you'll receive reward points on every booking. Our extended stay hotels in St. Michaels come with amenities like kitchens, laundries and recreational facilities, so even though you're miles away, you can still experience the comforts of home.
Reserve an extended stay hotel in St. Michaels and take all the time you want experiencing this wonderful destination. Along with being able to stay a few weeks or longer, these types of properties include features designed to make your visit nice and easy. Recreational facilities, kitchens and laundry areas are just the beginning. To find your ideal extended stay hotel, use Expedia's handy filters to search for properties based on amenities, price, location and more. Often offering weekly rates, extended stay hotels can be kinder to your budget compared to your standard accommodations.