Hotels with Pool & Resorts in Hillsmere Shores from AU$124

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Check availability on Hillsmere Shores Hotels with Pool

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Hillsmere Shores hotels with a pool

Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)
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, (1003)
"This place is extremely impressive!!! The room was clean, the view was AMAZING, and the staff were friendly. This is our new spot. Even the guy at the gift shop was really helpful and cool. "
United States
Stacy
The price is AU$178
includes taxes & fees
6 Jan - 7 Jan 2026
Rod 'N' Reel Resort
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool 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, (945)
"It was very comfortable and clean"
United States
Maria
The price is AU$144
includes taxes & fees
19 Jan - 20 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1001)
"Staff was friendly, courteous, and helpful."
United States
Donna
The price is AU$154
includes taxes & fees
26 Jan - 27 Jan 2026
St Michaels Inn
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is AU$251
includes taxes & fees
4 Jan - 5 Jan 2026
Kent Island Resort
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, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is AU$139
includes taxes & fees
1 Jan - 2 Jan 2026
Quality Inn Grasonville near Kent Island
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 AU$259
includes taxes & fees
7 Jan - 8 Jan 2026
Wylder Tilghman Island
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1000)
"Nice place "
United States
Tucker T
The price is AU$124
includes taxes & fees
7 Jan - 8 Jan 2026
Best Western Kent Narrows 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, (363)
"nice clean room staff very nice would stay again "
United States
mario
The price is AU$164
includes taxes & fees
1 Jan - 2 Jan 2026
Knapps Narrows Marina & Inn
Indoor pool, pool loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (686)
"friendly staff, clean room / lobby, nice bar, everything was great"
United States
William
The price is AU$192
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Kent Narrows & Marina
Outdoor pool
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (472)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is AU$228
includes taxes & fees
6 Jan - 7 Jan 2026
Anchored Inn at Hidden Harbour Marina
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

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"The front desk clerk was friendly and explained amenities clearly."
Jean 1-night trip
Posted 2 days ago
Comfort Inn Conference Center

Frequently asked questions

What are some accommodation options 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 centre. 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. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Offers buffet, an indoor pool and free self parking. Crowne Plaza Annapolis by IHG: Provides buffet, an indoor pool and free self parking. Graduate by Hilton Annapolis: Hotel located near Northwest Stadium. Offers 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 accommodation with an outdoor swimming pool if you'll be visiting Hillsmere Shores in the hottest months of July, August or June, when the average temp is 24°C. Accommodation 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 4°C.