The Best Hotels with a Pool in Sherwood, MD from NT$3,573 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. Historic Inns of Annapolis : Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis : Offers 2 outdoor pools, a children's pool, and a private beach. Crowne Plaza Annapolis by IHG : Offers daily, a seasonal outdoor pool, and free self parking. Hyatt Regency Chesapeake Bay : Hotel, 1-minute walk from Chesapeake Bay. Provides a seasonal outdoor pool, an indoor pool, and 2 restaurants.

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

Knapps Narrows Marina & Inn

Sherwood

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

NT$5,311 total

includes taxes & fees

Jul 13 - Jul 14

Holiday Inn Express Prince Frederick by IHG

Prince Frederick

Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.

NT$3,935 total

includes taxes & fees

Aug 2 - Aug 3

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$3,573 total

includes taxes & fees

Jul 26 - Jul 27

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$4,922 total

includes taxes & fees

Jul 13 - Jul 14

Best Western Kent Narrows Inn

Grasonville

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

NT$4,473 total

includes taxes & fees

Jul 15 - Jul 16

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.

NT$6,038 total

includes taxes & fees

Jul 26 - Jul 27

Fairfield Inn & Suites by Marriott Easton

Easton

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

NT$4,484 total

includes taxes & fees

Jul 19 - Jul 20

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$3,665 total

includes taxes & fees

Jul 19 - Jul 20

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Choose what matters most at hotels with a pool in Sherwood

Breakfast included

4 stars

Top Sherwood Hotel Reviews

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Menu on internet needs to be updated for restaurant"

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"This hotel is the best I’ve ever been to. The most extraordinary thing about this hotel is the staff. I would especially like to commend Antoine, Shuttle Driver and Amari at the front desk for going above and beyond their duties to help me during my stay! They are remrkably kind and considerate and I feel grateful to them for their courtesy and kindness! Of most remarkable note is that Amari went out of her way to help me with my reservation and when I offered to tip Antoine for his driver service, he refused to take it, stating that helping me was his pleasure! I was treated like family by everyone from the front desk, the restaurant and pool staff! I thoroughly enjoyed my stay and hope to return soon! I have written a detailed letter to management and hope that a copy of would be placed in their personnel file! These staff members are a true credit to the Hilton group of hotels!"

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. Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Offers 2 outdoor pools, a children's pool, and a private beach. Crowne Plaza Annapolis by IHG: Offers daily, a seasonal outdoor pool, and free self parking. Hyatt Regency Chesapeake Bay: Hotel, 1-minute walk from Chesapeake Bay. Provides a seasonal outdoor pool, an indoor pool, and 2 restaurants.

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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