Find Hotels with a Pool in Hillsmere Shores, MD

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Check availability on Hillsmere Shores Hotels with a Pool

Our top choices for Hillsmere Shores hotels with a pool

Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is ￥16,534
￥21,463 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Rod 'N' Reel Resort
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is ￥20,991
￥29,933 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wylder Tilghman Island
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1000)
"clean and comfy, friendly staff"
United States
Tamara
The price is ￥16,509
￥18,159 total
includes taxes & fees
Jan 13 - Jan 14, 2026
St Michaels Inn
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is ￥18,697
￥20,567 total
includes taxes & fees
Dec 14 - Dec 15
Knapps Narrows Marina & Inn
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (933)
"It was very comfortable and clean"
United States
Maria
The price is ￥13,528
￥15,017 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Pool
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1004)
"Parking was safe and free. Staff from breakfast did good service although breakfast was the same for 3 days. Location was perfect."
Canada
Ermelita
The price is ￥11,080
￥12,631 total
includes taxes & fees
Dec 28 - Dec 29
Best Western Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1002)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is ￥16,516
￥18,828 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Crowne Plaza Annapolis by IHG
Lobby
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (862)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ￥13,244
￥14,700 total
includes taxes & fees
Dec 21 - Dec 22
Quality Inn Grasonville near Kent Island
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1003)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is ￥14,803
￥16,875 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Country Inn & Suites by Radisson, Annapolis, MD
Indoor pool
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC
4.0 star property
Upper Marlboro
8.2 out of 10, Very Good, (1009)
"Great staff, rooms were clean. "
United States
ashley
The price is ￥14,248
￥16,100 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hotel Largo/Washington DC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsmere Shores Hotel Reviews

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"The staff was nice and the room was clean. My only complaint was that the remote in our room did not work well."
Ashlie 1-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Largo/Washington DC

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Frequently asked questions

What are some accommodations with pools in Hillsmere Shores?
DoubleTree by Hilton Hotel Annapolis: Hotel located near Northwest Stadium. Offers free self parking, an indoor pool, and a 24-hour fitness center. DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Hampton Inn Baltimore/Glen Burnie: Hotel located near Northwest Stadium. Features buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Provides buffet, a seasonal outdoor pool, and free self parking. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Features a snack bar/deli, an indoor pool, and buffet.
What is there to see and do in Hillsmere Shores?
The picturesque setting of Maryland Quiet Waters Park showcases the area's natural beauty. Discover sights such as Annapolis Landing Marina, Bay Ridge Beach, and Annapolis Maritime Museum during your stay.
When is the best time to book a hotel with a pool in Hillsmere Shores?
You may want to think about an accommodation with an outdoor swimming pool if you're planning to visit Hillsmere Shores in the hottest months of July, August, or June when the average temp is 75°F. Lodging offering 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 40°F.