The Best Hotels with a Pool in St. Michaels, MD from SAR 295 in 2026

Q: What are some accommodations with pools in St. Michaels?

St Michaels Inn : Features daily, a seasonal outdoor pool, and free self parking. Inn at Perry Cabin : Offers a full-service spa, an outdoor pool, and 2 bars. The Wildset : Features free self parking, an outdoor pool, and complimentary wireless internet access. George Brooks House B&B : Offers kitchens, a communal pool, and televisions. John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels! : Offers kitchens, a communal pool, and televisions.

A lighthouse on stilts with a green roof, surrounded by water and greenery.

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Our top choices for St. Michaels hotels with a pool

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

1. Inn at Perry Cabin

Downtown St. Michaels

Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.

SAR 1,895 total

includes taxes & fees

7 Dec - 8 Dec

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

2. Parsonage Inn

Downtown St. Michaels

Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons.

SAR 950 total

includes taxes & fees

13 Nov - 14 Nov

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

3. St Michaels Inn

St. Michaels

Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.

SAR 325 total

includes taxes & fees

17 Nov - 18 Nov

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

4. George Brooks House B&B

St. Michaels

Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.

SAR 739 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

5. The Oaks Waterfront

Easton

Scenic waterfront pool creates a summer paradise with views and easy water access.

SAR 1,817 total

includes taxes & fees

11 Dec - 12 Dec

A swimming pool with multiple people swimming and lounging around.

6. Knapps Narrows Marina & Inn

Sherwood

Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.

SAR 495 total

includes taxes & fees

15 Nov - 16 Nov

A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.

7. Hyatt Place Kent Narrows & Marina

Grasonville

Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.

SAR 559 total

includes taxes & fees

15 Nov - 16 Nov

An indoor swimming pool with lounge chairs and a no diving sign.

8. Holiday Inn Express Easton by IHG

Easton

Splashy indoor pool retreat creates a refreshing escape in the heart of Easton.

SAR 578 total

includes taxes & fees

19 Nov - 20 Nov

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

9. Best Western Plus Easton Inn & Suites

Easton

Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.

SAR 491 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

10. Hampton Inn Easton

Easton

Dive into refreshing luxury at this Easton hotel with a pristine indoor pool and fitness center for your aquatic escape.

SAR 528 total

includes taxes & fees

15 Nov - 16 Nov

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Choose what matters most at hotels with a pool in St. Michaels

Breakfast included

Hot tub

Top St. Michaels Hotel Reviews

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

George Brooks House B&B

St. Michaels

10/10 Excellent

Excellent B&B with a pool! the pool was clutch because we were there probably on the hottest days of the year so going in after a long day of walking around was nice. Used the pool until 10pm. Food was good, room was clean, people were nice. What else could you ask for. The only thing I noticed (and it wasn't a big deal) was the mirror in the room was too low on the wall (I'm 5'8 and still had to bend a little) and there was only one mirror so if you're in a hurry getting ready with your spouse...

Anonymous traveler

St Michaels Inn

St. Michaels

10/10 Excellent

Lori

The Oaks Waterfront

Easton

10/10 Excellent

William

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

A swimming pool with lounge chairs and a pergola under a clear sky.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A pool with two Adirondack chairs and a basket of items on the grass.

The Inn at Tacaro Estate

Tracys Landing

10/10 Excellent

ian

A swimming pool with blue lounge chairs and a building with balconies in the background.

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

Wylder Tilghman Island

Tilghman

10/10 Excellent

We had a great time at the Wylder Inn on Tilghman Island (20-21 May). This is a great spot for a quick getaway, and there are many things to do on site and in the area if you want to stay longer. The staff was welcoming and responsive from our arrival to departure when our key was collected from our car so we didn't have to get out in the rain. The Continental Breakfast had a variety of items to start the day right and the fire pits provided a relaxing venue at the end of the day. We look...

Alan

Hampton Inn Easton

Easton

10/10 Excellent

Anonymous traveler

Holiday Inn Express Easton by IHG

Easton

10/10 Excellent

Belinda

Best Western Plus Easton Inn & Suites

Easton

10/10 Excellent

Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...

Nancy

An indoor swimming pool with clear views of boats and water.

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Excellent

Kathie

A hotel pool area with two pools, chairs, and a sunshade.

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Julie

Frequently Asked Questions

What are some accommodations with pools in St. Michaels?

St Michaels Inn: Features daily, a seasonal outdoor pool, and free self parking. Inn at Perry Cabin: Offers a full-service spa, an outdoor pool, and 2 bars. The Wildset: Features free self parking, an outdoor pool, and complimentary wireless internet access. George Brooks House B&B: Offers kitchens, a communal pool, and televisions. John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!: Offers kitchens, a communal pool, and televisions.

What is there to see and do in St. Michaels?

Make a point to visit attractions like Church Cove Park and Chesapeake Bay Maritime Museum. Discover sights such as Saint Michaels Town Hall, St. Michaels Marina, and St. Michaels Winery during your stay. The seafood restaurants, historic landmarks, and shopping are just some of the things to enjoy while you're in the area.

When is the best time to book a hotel with a pool in St. Michaels?

You may want to consider an accommodation with an outdoor swimming pool if you plan to visit St. Michaels in the warmest months of July, August, or June when the average temperature is 75°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 41°F.

Find Hotels with a Pool in St. Michaels, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for St. Michaels hotels with a pool

1. Inn at Perry Cabin

2. Parsonage Inn

3. St Michaels Inn

4. George Brooks House B&B

5. The Oaks Waterfront

6. Knapps Narrows Marina & Inn

7. Hyatt Place Kent Narrows & Marina

8. Holiday Inn Express Easton by IHG

9. Best Western Plus Easton Inn & Suites

10. Hampton Inn Easton

Choose what matters most at hotels with a pool in St. Michaels

Top St. Michaels Hotel Reviews

Inn at Perry Cabin

10/10 Excellent

Frequently Asked Questions

What are some accommodations with pools in St. Michaels?

What is there to see and do in St. Michaels?

When is the best time to book a hotel with a pool in St. Michaels?