The Best Hotels with a Pool in Sherwood, MD from ₩105,079 in 2026

Q: What are some accommodations with pools in Sherwood?

Knapps Narrows Marina & Inn : Hotel, 14-minute walk from Chesapeake Bay. Features daily, a seasonal outdoor pool, and free self parking. DoubleTree by Hilton Hotel Annapolis : Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis : Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. Crowne Plaza Annapolis by IHG : Offers daily, a seasonal outdoor pool, and free self parking. Graduate by Hilton Annapolis : Features buffet, a seasonal outdoor pool, and complimentary wireless internet access.

A large brick house with a green roof, surrounded by lush gardens and trees.

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Our top choices for Sherwood hotels with a pool

A swimming pool with multiple people swimming and lounging around.

1. Knapps Narrows Marina & Inn

Sherwood

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

₩176,029 total

includes taxes & fees

Nov 30 - Dec 1

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

2. Inn at Perry Cabin

Downtown St. Michaels

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

₩673,310 total

includes taxes & fees

Dec 7 - Dec 8

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.

₩115,587 total

includes taxes & fees

Nov 15 - Nov 16

A rectangular swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a view of the sea.

4. Wylder Tilghman Island

Tilghman

Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.

₩343,923 total

includes taxes & fees

Dec 1 - Dec 2

A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.

5. Rod 'N' Reel Resort

Chesapeake Beach

Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.

₩259,027 total

includes taxes & fees

Dec 3 - Dec 4

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

6. Holiday Inn Express Easton by IHG

Easton

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

₩205,722 total

includes taxes & fees

Nov 19 - Nov 20

A two-story house with a front porch, white siding, and a black front door.

7. The Oaks Waterfront

Easton

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

₩645,585 total

includes taxes & fees

Nov 15 - Nov 16

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

8. 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.

₩366,727 total

includes taxes & fees

Nov 19 - Nov 20

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

9. Fairfield Inn & Suites by Marriott Easton

Easton

Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.

₩185,783 total

includes taxes & fees

Nov 26 - Nov 27

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

10. 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.

₩262,723 total

includes taxes & fees

Nov 16 - Nov 17

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Choose what matters most at hotels with a pool in Sherwood

Breakfast included

4 stars

Top Sherwood Hotel Reviews

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

The Oaks Waterfront

Easton

10/10 Excellent

William

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

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

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

Holiday Inn Express Easton by IHG

Easton

10/10 Excellent

Belinda

Rod 'N' Reel Resort

Chesapeake Beach

10/10 Excellent

Huge resort in a small, well kept town! Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable. There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other things)... We were in a hurry to get home so did not try any of the breakfast places that the desk clerk recommended. The staff guy that checked us in was SUPER nice and helpful!

Kathie

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

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

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

Hampton Inn Easton

Easton

10/10 Excellent

Anonymous traveler

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

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 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 tiled edge, surrounded by blue lounge chairs and white tables.

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

The Inn at Tacaro Estate

Tracys Landing

10/10 Excellent

ian

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

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Excellent

Kathie

A large indoor swimming pool with clear water, tiled walls, and a ceiling with ventilation ducts.

Holiday Inn Express Cambridge by IHG

Cambridge

10/10 Excellent

Charles A

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

Frequently Asked Questions

What are some accommodations with pools in Sherwood?

Knapps Narrows Marina & Inn: Hotel, 14-minute walk from Chesapeake Bay. Features daily, a seasonal outdoor pool, and free self parking. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. Crowne Plaza Annapolis by IHG: Offers daily, a seasonal outdoor pool, and free self parking. Graduate by Hilton Annapolis: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access.

What is there to see and do in Sherwood?

The picturesque setting of Goat Island showcases the area’s natural beauty. Discover sights such as Knapp's Narrows Marina & Inn during your stay.

When is the best time to book a hotel with a pool in Sherwood?

You may want to think about a place to stay that has an outdoor pool if you're planning to visit Sherwood in the hottest months of July, August, or June when the average temperature is 75°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 41°F.

Find Hotels with a Pool in Sherwood, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sherwood hotels with a pool

1. Knapps Narrows Marina & Inn

2. Inn at Perry Cabin

3. St Michaels Inn

4. Wylder Tilghman Island

5. Rod 'N' Reel Resort

6. Holiday Inn Express Easton by IHG

7. The Oaks Waterfront

8. Parsonage Inn

9. Fairfield Inn & Suites by Marriott Easton

10. George Brooks House B&B

Choose what matters most at hotels with a pool in Sherwood

Top Sherwood Hotel Reviews

Knapps Narrows Marina & Inn

10/10 Excellent

Frequently Asked Questions

What are some accommodations with pools in Sherwood?

What is there to see and do in Sherwood?

When is the best time to book a hotel with a pool in Sherwood?