Find Hotels with a Pool in Hillsmere Shores, MD

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Check availability on Hillsmere Shores Hotels with a Pool

Top Hillsmere Shores Hotels with a Pool

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

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
  • Indoor pool
  • Pool loungers
  • Near the beach
8.4 out of 10, Very Good, (1000)
Sparkling waters beckon at dual pools, where cabanas offer shaded luxury beside the marina. Beyond refreshing dips, guests enjoy complimentary bicycles, kayaking adventures, and nearby beach access, creating a complete coastal escape.
$129 nightly
The price is $142
Nov 23 - Nov 24
Total with taxes and fees
Rod 'N' Reel Resort
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (353)
Marina-side seasonal pool creates a serene retreat overlooking Chesapeake Bay waters. Guests appreciate the immaculate rooms with private balconies, complimentary bicycles for island adventures, and boat tours launching steps away.
$100 nightly
The price is $110
Nov 23 - Nov 24
Total with taxes and fees
Knapps Narrows Marina & Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

2.5 star property
St. Michaels
  • Pool loungers
8.2 out of 10, Very Good, (1002)
Sparkling waters beckon at the seasonal outdoor pool, complete with sun loungers and umbrellas from May through September. Conveniently situated near Chesapeake Bay Maritime Museum, this hotel offers continental breakfast and garden views after invigorating local hikes.
$107 nightly
The price is $118
Dec 14 - Dec 15
Total with taxes and fees
St Michaels Inn
Indoor pool, open 5 AM to 11 PM, sun loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1000)
Waterfront serenity awaits at the indoor pool, complete with comfortable sun loungers and extended hours from 5 AM to 11 PM. Steps from the marina, this hotel combines aquatic pleasure with scenic beauty and a modern fitness center.
$102 nightly
The price is $113
Nov 23 - Nov 24
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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

2.5 star property
Grasonville
  • Pool loungers
9.2 out of 10, Wonderful, (919)
Splashing in the seasonal outdoor pool reveals stunning Chesapeake Bay vistas, creating a waterfront oasis complete with sun loungers and umbrellas. Nearby adventures include hiking trails, kayaking, and sailing for the perfect coastal getaway.
$107 nightly
The price is $119
Dec 15 - Dec 16
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool
Comfort Inn Conference Center

Comfort Inn Conference Center

2.5 star property
Bowie
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
9.2 out of 10, Wonderful, (1004)
Sparkling waters await at the seasonal outdoor pool, open June through August for sun-soaked enjoyment. Located near Six Flags America, this hotel combines comfortable pillowtop beds with American cuisine at Chessies Chesapeake Grill after poolside relaxation.
$99 nightly
The price is $112
Nov 17 - Nov 18
Total with taxes and fees
Comfort Inn Conference Center
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
Annapolis
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (1004)
Surrounded by an atmosphere of quiet serenity, the indoor pool invites leisurely swims while the inviting hot tub soothes tired muscles. Spacious, clean rooms and friendly staff complete this comfortable Maryland retreat.
$93 nightly
The price is $106
Dec 7 - Dec 8
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
  • Indoor pool
8.8 out of 10, Excellent, (1000)
Swimming enthusiasts revel in the refreshing indoor pool at this Annapolis hotel, complemented by a 24-hour fitness center. Positioned near Westfield Annapolis Mall, guests appreciate the convenient restaurant, bar, and thoughtful amenities like free parking.
$93 nightly
The price is $106
Dec 7 - Dec 8
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
7.8 out of 10, Good, (849)
Cooling waters await at the seasonal outdoor pool, open 24 hours from May to October. This hotel sits near the Chesapeake Exploration Center, offering comfortable rooms, a complimentary breakfast buffet, and friendly service praised by past guests.
$94 nightly
The price is $104
Nov 23 - Nov 24
Total with taxes and fees
Quality Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
  • On private beach
8.8 out of 10, Excellent, (88)
Seasonal outdoor swimming beckons travelers from March through October at this waterfront haven. Complementing the pool, a private beach, sauna, and free bicycles create perfect relaxation opportunities along the river's edge.
$179 nightly
The price is $197
Dec 4 - Dec 5
Total with taxes and fees
Wylder Tilghman Island
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Wonderful country inn!"
Jennifer 4-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some accommodations with pools in Hillsmere Shores?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Provides buffet, an indoor pool, and free self parking. Comfort Inn Largo-Washington DC East: Features buffet, an indoor pool, and free self parking. Country Inn & Suites by Radisson, Annapolis, MD: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool, and free self parking.
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.

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