
Places to stay in Saint Michaels
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Top-rated places to stay in Saint Michaels
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Popular amenities for Saint Michaels places to stay
Dog friendly places to stay in Saint Michaels

Coastal Oasis On The Chesapeake, King Bd sleeps 12
My mom, sisters, friends and I enjoyed a relaxing fun filled time at the Coastal Oasis at the Chesapeake for our Mother's Day Retreat. The view is amazing and truly can be seen from every room in the house! Being able to see the beauty and calmness of the water helped each of us kick back and let the stress melt away. The big dinning room table allowed all of us all to enjoy breakfasts, dinners and touching conversations together. My guests loved the décor and raved about every detail. The beds and furniture were comfortable and house clean. I would definitely come back!

Waterfront, Dog-friendly, Hot Tub, Peleton
This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!

The Crab House - a Private, Waterfront Guest House
The pictures do this place no justice whatsoever. It was absolutely beautiful and very homey.

River Front, Private Single Family Home
We had a great weekend at this cottage. Comfortable layout, great dock, and a beautiful view. We hope to return.

Historic Downtown in-law suite
Laurie’s place was just liked it is described. It’s located in a beautiful area and walkable to all the attractions in Annapolis Maryland. I would recommend it and I would stay there again if ever back in Annapolis! Thanks for wonderful stay!

Luxe Modern Chesapeake Waterfront Oasis - 5 Star
TL;DR: this was easily one of our favorite Airbnb experiences. We absolutely cannot wait to come back. We spent a week at Evan's cottage for my wife's birthday. Our party included 5 adults, 2 small pups, and an infant and there was more than enough room for all of us to stay comfortably. Evan was an incredible host- promptly responsed to all of our inquires, and regularly checked in to make sure if we needed anything. The house itself. Hot damn. It is stunning. The landscaping envelopes you in lush greens and blooming flowers, the view overlooking the Chesapeake is amazing, and the house is filled with every amenity you could imagine. (Huge shoutout to all the baby gear - as new parents, this was a lifesaver). The beds we're cozy, the kitchen was *stocked*, and the interior design was ::chef's kiss:: While the immediate area (10ish min drive) has everything covered for basics, you're only a quick trip into Annapolis to get anything else you may need for your trip.

Peaceful Waterfront Retreat on The Bay
It’s our second stay at Camp Maier and we are already planning to come back. As soon as we step in, we feel calmed by the view and the comfortable space. The place has had a fresh coat of paint since we were here last, and we appreciated the kitchen upgrades too. We loved pizza at Cryptic Pizza in Solomons Island and a walk with dogs at Flag Ponds nature park. Even found a small fossilized shark tooth! A magical time. Thank you.

The Little Gypsy BoHome
Wonderful place - pictures do not do it justice. Home is spotless and beautifully furnished! We had a great time relaxing on our babymoon. Lots of great restaurants close by and so much to do at the house you never have to leave. Really appreciated the details such as the coloring station and ample beach towels. Hope to stay again in the future!
Other great vacation rentals in Saint Michaels

Saint Michaels Waterfront Home
Beautiful location and home to spend over Memorial Day weekend. The house had everything we needed and was a comfortable stay. Brandon was very nice and accommodating.

Sailor's Cottage - Private Waterfront
A peaceful and charming place to stay! It was more than I hoped it would be.

Waterfront Modern Guest Barn
Overall, I enjoyed the place. The barn was minimalistic and nice for photos. The best part was the waterfront view. The house was very clean and pretty kid friendly (a few high chairs included). The kitchen had the bare minimum to cook and grill with but I wouldn’t say it was fully stocked. I would say in general that we enjoyed our stay. The kayaks were wonderful.

*Waterfront Sunset Bayview* sleeps 6
The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)

Waterfront Farmhouse Meets Modern Luxury
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

Kent Island Escape
The place was wonderful. The house was clean. The beds were comfortable. The kitchen was more than well equipped. The setting was beautiful. The outdoors was perfect. Great outdoor furniture. The Bayview was unbelievable. The house in relationship to recreation is spot on. I can’t say enough great things about the place. I will definitely be booking again and again.

Eastern Shore Retreat!
We had a wonderful stay in Easton. The house was perfect for our visit. Pristinely clean, comfortable, well stocked and the setting was peacefully beautiful. Everything about our stay exceeded our expectations.

Cottage 2 Egret
What a joy of a stay. The host is so incredibly welcoming to their beautiful property. It was exactly what you need for time in St. Michael’s. We would absolutely stay here again.
Quick stats about vacation rentals in Saint Michaels
Total rentals
40 properties
Nightly prices starting at
G$27,168 GYD before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Saint Michaels?
Yes! Work meets play with ease at over 20 vacation rentals in Saint Michaels featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Saint Michaels?
Experience the best of Saint Michaels with our house rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Saint Michaels?
Four-legged friends are welcome in Saint Michaels. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Saint Michaels have wifi?
Absolutely! We offer over 20 house rentals with wifi in Saint Michaels. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Saint Michaels have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Saint Michaels. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Saint Michaels have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Saint Michaels. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Saint Michaels?
Saint Michaels has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there Saint Michaels vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Saint Michaels, available on Airbnb. Make a splash and soak up the sun in style!
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Hampden
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- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- District Wharf
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- Crystal Beach Manor, Earleville, MD
- Maryland Renaissance Festival
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