Find Extended Stay Hotels in St. Michaels, MD

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Top St. Michaels Extended Stay Hotels | Reserve now, pay later

1 bedroom, hypo-allergenic bedding, desk, blackout drapes
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1011)
"Great place to stay Friendly staff secure rooms Thank you "
$97 nightly
The price is $110
Nov 2 - Nov 3
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Lake
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (55)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
$156 nightly
The price is $173
Nov 2 - Nov 3
Total with taxes and fees
Inn at Huntingfield Creek
Lobby
Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & Suites
2.5 star property
9.2 out of 10, Wonderful, (1002)
"Excellent staff, very clean room, good hotel breakfast "
$119 nightly
The price is $131
Nov 9 - Nov 10
Total with taxes and fees
Best Western Plus Easton Inn & Suites
Exterior
Candlewood Suites Annapolis by IHG
Candlewood Suites Annapolis by IHG
2.5 star property
8.8 out of 10, Excellent, (142)
"This hotel was a nice surprise tucked away in a quiet area, yet close to everything Annapolis has to offer. The woman who checked us in was very welcoming and helpful!"
$97 nightly
The price is $111
Oct 19 - Oct 20
Total with taxes and fees
Candlewood Suites Annapolis by IHG
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (638)
"Great location and rooms. Great place!"
$144 nightly
The price is $160
Oct 21 - Oct 22
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
Egyptian cotton sheets, premium bedding, pillowtop beds, desk
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (917)
"Had a great stay."
$87 nightly
The price is $99
Nov 9 - Nov 10
Total with taxes and fees
Sonesta ES Suites Annapolis
Premium bedding, pillowtop beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis
2.5 star property
8.2 out of 10, Very Good, (1008)
"We had a nice stay. "
$96 nightly
The price is $109
Nov 3 - Nov 4
Total with taxes and fees
Hampton Inn & Suites Annapolis
Front of property
The Oaks Waterfront
The Oaks Waterfront
4.0 star property
10.0 out of 10, Exceptional, (38)
"Loved the Oaks! Fabulous accommodations and excellent staff"
$459 nightly
The price is $505
Oct 15 - Oct 16
Total with taxes and fees
The Oaks Waterfront
Property grounds
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
$2,620 nightly
The price is $2,987
Oct 15 - Oct 16
Total with taxes and fees
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
$280 nightly
The price is $297
Oct 15 - Oct 16
Total with taxes and fees
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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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Find out more about St. Michaels

Discover top St. Michaels attractions

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.

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Most booked related extended stays in St. Michaels in 2025

St. Michaels apart-hotels
Apart-hotels for extended stays
Apart-hotels for extended stays
St. Michaels vacation homes with a kitchen
Vacation homes with a kitchen
Vacation homes with a kitchen

Frequently asked questions

What are the best long-term hotels in St. Michaels?
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.
What are the top pet-friendly extended stay hotels in St. Michaels?
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.
What's the best extended stay hotel in downtown St. Michaels?
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.
What are the best extended stay hotels with kitchens in St. Michaels?
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.
Can I find extended stay hotels with pools in St. Michaels?
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.
What are the top extended stay hotels with 2 bedrooms in St. Michaels?
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.
Why book an extended stay hotel in St. Michaels through Expedia?
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.
What can I expect from an extended stay hotel?
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.

Top St. Michaels Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Our night at your hotel was just fine! Room was clean. Supply toiletries, towels for the bath and kitchen were as expected, neat and plentiful. There was a creak in the bathroom door, but that is a nitpick. Coffee maker was easy to operate. Breakfast was as expected, with some delay when coffee carafe and food service trays were empty. I would go back."
Edmund 1-night trip
Posted 1 day ago
Sonesta ES Suites Annapolis
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
" Very clean and fresh room The TV screen already had my name on it !"
Jean 1-night trip
Posted 7 days ago
SpringHill Suites by Marriott Annapolis

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