The Best Hotels with a Pool in Sherwood, MD from NT$3,356 in 2026

Q: What are some accommodations with pools in Sherwood?

Historic Inns of Annapolis : Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis : Features 2 outdoor pools, a children's pool, and a private beach. Sonesta ES Suites Annapolis : Offers complimentary wireless internet access, an indoor pool, and televisions. Hyatt Regency Chesapeake Bay : Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Courtyard by Marriott Annapolis : Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.

Gardens and large home at Sherwood Gardens Park, in Baltimore, M

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Our top choices for Sherwood hotels with a pool

Knapps Narrows Marina & Inn

Sherwood

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

NT$5,182 total

includes taxes & fees

Jun 7 - Jun 8

Quality Inn Grasonville near Kent Island

Grasonville

Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.

NT$3,704 total

includes taxes & fees

Jun 16 - Jun 17

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St. Michaels

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

NT$4,674 total

includes taxes & fees

Jun 15 - Jun 16

Best Western Kent Narrows Inn

Grasonville

Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.

NT$4,016 total

includes taxes & fees

Jun 10 - Jun 11

Quality Inn

Easton

Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.

NT$3,494 total

includes taxes & fees

Jun 23 - Jun 24

Best Western Plus Easton Inn & Suites

Easton

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

NT$4,802 total

includes taxes & fees

May 31 - Jun 1

Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers

Rod 'N' Reel Resort

Chesapeake Beach

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

NT$5,979 total

includes taxes & fees

Jun 18 - Jun 19

Kent Island Resort

Stevensville

Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.

NT$6,440 total

includes taxes & fees

Jun 1 - Jun 2

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Choose what matters most at hotels with a pool in Sherwood

Breakfast included

4 stars

Top Sherwood Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"Loved the Navy inspired decor and theme, location, valet parking, bathroom accouterments. Would definitely choose The Graduate again.."

Hyatt Regency Chesapeake Bay

8/10 Good

"Hotel is beautiful , grounds are beautiful ! Staff is amazing ! Only disappointment was the pool situation - Seems like if you are there during the week or if weather isn’t perfect restaurants and amenities aren’t available as expected. It wasn’t raining just overcast, and it was warm and humid out but outdoor pools closed 80% of our three days bc “short staffed,” “broken heater “ or “ the rain the days prior made the pool water cold.” No activities or events during the weekdays for kids or adults , Just saying :( No glow golf for kids , asked about it a few times. But beautiful place and wonderful staff! Would try it again ! Only one restaurant Open for breakfast all three days."

SpringHill Suites by Marriott Annapolis

6/10 Okay

"Carpet was old and needed replacement and cleaning. Quite smelly Once I mentioned to the front desk, they got maintenance on it and reported it to corporate. Needs some updates. Could not use the gym or pool area Gym smelled bad not cleaned though lots of housekeeping around and the pool water was and hot tub were merky. It was also insane that they were charging for unsecured parking that used to be free."

Frequently asked questions

What are some accommodations with pools in Sherwood?

Historic Inns of Annapolis: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Features 2 outdoor pools, a children's pool, and a private beach. Sonesta ES Suites Annapolis: Offers complimentary wireless internet access, an indoor pool, and televisions. Hyatt Regency Chesapeake Bay: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Courtyard by Marriott Annapolis: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.

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.

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