Find Hotels with a Pool in Sherwood, MD

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Check availability on Sherwood Hotels with a Pool

Tonight
26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Sherwood 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, (1001)
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 AED 372
AED 486 total
includes taxes & fees
9 Dec - 10 Dec
Rod 'N' Reel Resort
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, (820)
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 AED 297
AED 326 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
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, (357)
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 AED 367
AED 404 total
includes taxes & fees
29 Nov - 30 Nov
Knapps Narrows Marina & Inn
Outdoor pool
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
  • Outdoor pool
8.2 out of 10, Very Good, (1001)
Sparkling waters beckon at the well-maintained outdoor pool, a highlight praised by guests for its cleanliness and welcoming atmosphere. After swimming, visitors can energize at the 24-hour fitness center or dine at the Garden Grille and Bar.
The price is AED 247
AED 281 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis
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.
The price is AED 384
AED 422 total
includes taxes & fees
4 Dec - 5 Dec
St Michaels Inn
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, (686)
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 AED 379
AED 421 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Prince Frederick by IHG
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (126)
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 AED 409
AED 580 total
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
  • Indoor pool
  • Hot tub
8.0 out of 10, Very Good, (1005)
Sparkling waters await in the pristine indoor swimming pool, complemented by a rejuvenating hot tub and sauna. Active travelers appreciate the nearby hiking trails while enjoying spotless accommodations with 49-inch TVs and refrigerators.
The price is AED 338
AED 375 total
includes taxes & fees
4 Dec - 5 Dec
Best Western Kent Narrows 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, (853)
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 AED 320
AED 355 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
Indoor pool, sun loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (663)
Pool loungers invite guests to unwind beside the tranquil indoor pool after exploring nearby trails and beaches. With stunning waterfront vistas, delicious breakfast options, and spacious, comfortable rooms, this hotel offers a serene island retreat.
The price is AED 426
AED 473 total
includes taxes & fees
4 Dec - 5 Dec
Hyatt Place Kent Narrows & 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 Sherwood Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"The room was clean and the amenities were great! I loved the lobby and valet very fast and professional. I will stay here again. "
Scott 3-night trip
Posted 3 days ago
The Westin Annapolis

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Frequently asked questions

What are some accommodations with pools in Sherwood?
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access: Features a private beach, a communal pool, and kitchens. Historic Inns of Annapolis: Offers 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. Graduate by Hilton Annapolis: Features 2 outdoor pools, a children's pool, and a private beach. Sonesta ES Suites Annapolis: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.
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.