Hotels with Swimming Pool in Sherwood, Maryland

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Check availability on Sherwood Hotels with Swimming Pool

Top Sherwood Hotels with Swimming 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.
The price is P5,321
P7,085 total
includes taxes & fees
Nov 20 - Nov 21
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, (355)
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.
The price is P5,893
P6,482 total
includes taxes & fees
Nov 23 - Nov 24
Knapps Narrows Marina & Inn
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, (851)
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.
The price is P5,587
P6,202 total
includes taxes & fees
Dec 10 - Dec 11
Quality Inn
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.6 out of 10, Good, (816)
Poolside relaxation awaits after exploring the city center at this welcoming hotel. Spacious, clean rooms provide comfort while friendly staff ensure exceptional service. Guests appreciate the quiet atmosphere, complimentary breakfast, and convenient amenities.
The price is P4,758
P5,234 total
includes taxes & fees
Dec 7 - Dec 8
Quality 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, (1000)
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.
The price is P6,551
P7,206 total
includes taxes & fees
Nov 23 - Nov 24
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.
The price is P5,626
P6,245 total
includes taxes & fees
Nov 26 - Nov 27
Hilton Garden Inn Kent Island Marina
Indoor pool
Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

2.5 star property
Prince Frederick
  • Indoor pool
  • Near the beach
8.8 out of 10, Excellent, (683)
Swimming enthusiasts savor the warm, inviting indoor pool, accessible from early morning until evening. Located near Calvert Cliffs State Park and Running Hare Vineyard, this spotless hotel earns consistent praise for its helpful staff and delicious breakfast variety.
The price is P6,069
P7,391 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express Prince Frederick by IHG
Pool
Best Western Annapolis

Best Western Annapolis

2.5 star property
Annapolis
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.8 out of 10, Good, (1003)
Sparkling clean waters welcome swimmers to this hotel's inviting outdoor pool, perfect for unwinding after exploring nearby downtown attractions. Comfortable accommodations, helpful multilingual staff, and a fitness center round out this well-located retreat.
The price is P4,031
P4,595 total
includes taxes & fees
Dec 19 - Dec 20
Best Western Annapolis
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (125)
Sparkling waters welcome swimmers to this seasonal retreat where comfortable loungers await beneath shade umbrellas. Beyond the refreshing pool, adventures beckon with complimentary bicycles, kayaking, and fishing along the picturesque Chesapeake Bay.
The price is P7,383
P10,259 total
includes taxes & fees
Dec 1 - Dec 2
Kent Island Resort
Indoor pool
Hampton Inn Easton

Hampton Inn Easton

2.5 star property
Easton
  • Indoor pool
9.0 out of 10, Wonderful, (546)
Aquatic adventures await in the indoor pool, accessible from morning to evening after a complimentary breakfast buffet. The fitness center, immaculate rooms, and consistently praised staff complete this comfortable retreat for travelers seeking both activity and relaxation.
The price is P6,466
P7,112 total
includes taxes & fees
Nov 25 - Nov 26
Hampton Inn Easton
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 Sherwood Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Amazing "
Barbara 1-night trip
Posted 5 days ago
The Westin Annapolis

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Frequently asked questions

What are some accommodations with pools in Sherwood?
Historic Inns of Annapolis: Features sun loungers, a pool, and complimentary wireless internet access. Sonesta ES Suites Annapolis: Offers a private beach, a communal pool, and kitchens. Crowne Plaza Annapolis by IHG: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. Hilton Garden Inn Annapolis Downtown: Offers a snack bar/deli, an indoor pool, and free self parking.
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.