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

Guest favorite
A spacious living area features large glass windows that frame a panoramic view of the Chesapeake Bay. Natural light illuminates the room, highlighting the wooden ceiling and modern decor. A seating arrangement overlooks an inviting outdoor patio with garden furniture, creating a seamless connection to the outdoors.
Home in Lusby
4.96 out of 5 average rating, 144 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

JoyceRating, 5 stars1 month ago
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!
Top guest favorite
A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.
Home in North Beach
5 out of 5 average rating, 141 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

StephanieRating, 5 stars2 days ago
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!
Guest favorite
A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.
Guesthouse in Glen Burnie
4.93 out of 5 average rating, 343 reviews

The Crab House - a Private, Waterfront Guest House

TasharaRating, 5 stars2 weeks ago
The pictures do this place no justice whatsoever. It was absolutely beautiful and very homey.
Top guest favorite
A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.
Home in Grasonville
4.95 out of 5 average rating, 271 reviews

River Front, Private Single Family Home

AnnaRating, 5 stars2 weeks ago
We had a great weekend at this cottage. Comfortable layout, great dock, and a beautiful view. We hope to return.
Guest favorite
A serene outdoor patio area features manicured hedges and a stone path. A seating arrangement is visible, surrounded by greenery. A colorful flag and artwork hang on the fence, while flowering trees add a natural touch to the space, providing a cozy atmosphere.
Home in Annapolis
4.97 out of 5 average rating, 177 reviews

Historic Downtown in-law suite

BrianRating, 5 stars4 weeks ago
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!
Top guest favorite
The modern two-story cottage is set against a backdrop of lush greenery, featuring a well-manicured lawn and vibrant flower beds. Elevated views of the waterfront are visible in the distance, while a stone pathway leads to the front entrance adorned with wooden double doors.
Home in Shady Side
5 out of 5 average rating, 169 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

MarkRating, 5 stars2 weeks ago
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.
Guest favorite
A wooden staircase illuminated by soft lights leads down to a private dock. Reflections of trees and evening sky are seen on the calm water of St. Leonard Creek. A sailboat is moored at the end of the dock, adding to the serene waterside ambiance.
Cabin in Lusby
4.9 out of 5 average rating, 266 reviews

Peaceful Waterfront Retreat on The Bay

SarahRating, 5 stars6 days ago
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.
Top guest favorite
A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.
Home in Tracys Landing
4.99 out of 5 average rating, 212 reviews

The Little Gypsy BoHome

Jane AnnRating, 5 stars1 week ago
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

Guest favorite
Home in Newcomb
4.98 out of 5 average rating, 53 reviews

Saint Michaels Waterfront Home

KaleighRating, 5 stars2 weeks ago
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.
Top guest favorite
Cottage in Oxford
5 out of 5 average rating, 15 reviews

Sailor's Cottage - Private Waterfront

KathleenRating, 5 stars1 week ago
A peaceful and charming place to stay! It was more than I hoped it would be.
Guest favorite
The modern guest barn is depicted against a serene river setting, framed by trees. Its large glass windows reflect the soft colors of the sunset, while the grassy lawn leads gently to the water's edge, creating a peaceful atmosphere.
Barn in Queenstown
4.98 out of 5 average rating, 63 reviews

Waterfront Modern Guest Barn

ElaineRating, 5 stars1 month ago
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.
Top guest favorite
A modern kitchen features sleek white cabinetry and a minimalist design. The countertop is seamlessly integrated with a coffee maker, offering convenience for guests. Bright lighting enhances the spacious feel, while wood flooring adds a warm touch to the contemporary aesthetic.
Home in Chester
5 out of 5 average rating, 39 reviews

*Waterfront Sunset Bayview* sleeps 6

KellyRating, 5 stars1 week ago
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)
Guest favorite
A charming neoclassical farmhouse is observed, set among leafy trees. A wide gravel driveway leads to the welcoming front porch, which features white columns. Lush greenery surrounds the home, enhancing the tranquil setting of the property.
Home in Chester
4.95 out of 5 average rating, 95 reviews

Waterfront Farmhouse Meets Modern Luxury

TrishRating, 5 stars1 week ago
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.
Superhost
A serene outdoor setting is captured at sunset, with a wooden dining table positioned on a patio. Snow blankets the ground, contrasting with the warm orange and purple hues of the sky. Silhouetted chairs are arranged around the table, overlooking the water.
Home in Chester
5 out of 5 average rating, 7 reviews

Kent Island Escape

CarolynRating, 5 stars1 month ago
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.
Top guest favorite
Four white Adirondack chairs are positioned in a grassy area, facing a serene pond. The surrounding landscape features tall trees and lush greenery, providing a tranquil natural setting. Bright sunlight enhances the peaceful atmosphere of the outdoor space.
Home in Easton
5 out of 5 average rating, 34 reviews

Eastern Shore Retreat!

BethRating, 5 stars2 weeks ago
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.
Superhost
A set of white Adirondack chairs is arranged facing a calm body of water, providing an inviting spot for relaxation. A small white table accompanies the chairs on a grassy area, with trees lining the background. The tranquil water reflects the sky, enhancing the serene setting.
Cabin in Saint Michaels
4.75 out of 5 average rating, 4 reviews

Cottage 2 Egret

AshleyRating, 5 stars4 weeks ago
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!

Destinations to explore

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  5. Saint Michaels