Find Hotels with a Pool in Sherwood, MD

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Check availability on Sherwood Hotels with a Pool

Tonight
Dec 6 - Dec 7
Tomorrow
Dec 7 - Dec 8
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

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
8.4 out of 10, Very Good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is ￥16,517
￥21,441 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Rod 'N' Reel Resort
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
9.2 out of 10, Wonderful, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is ￥12,271
￥13,620 total
includes taxes & fees
Dec 18 - Dec 19
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

2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1001)
"clean and comfy, friendly staff"
United States
Tamara
The price is ￥16,493
￥18,141 total
includes taxes & fees
Jan 7 - Jan 8, 2026
St Michaels Inn
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (859)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ￥13,203
￥14,655 total
includes taxes & fees
Dec 21 - Dec 22
Quality Inn
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
7.6 out of 10, Good, (824)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ￥12,543
￥13,798 total
includes taxes & fees
Dec 14 - Dec 15
Quality Inn
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
9.4 out of 10, Exceptional, (359)
"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 ￥18,640
￥20,504 total
includes taxes & fees
Dec 8 - Dec 9
Knapps Narrows Marina & 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
9.0 out of 10, Wonderful, (1003)
"Room was great! In room tub was a bit smaller than I was expecting but still quite adequate! View from room was very nice."
United States
Madeline
The price is ￥16,030
￥17,793 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Kent Island Marina
Pool
Best Western Annapolis

Best Western Annapolis

2.5 star property
Annapolis
7.8 out of 10, Good, (1001)
"Clean room, nice staff and plenty of parking "
United States
Chauntese
The price is ￥11,325
￥12,911 total
includes taxes & fees
Dec 19 - Dec 20
Best Western Annapolis
Seasonal outdoor pool
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 ￥20,970
￥29,902 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Wylder Tilghman Island
Outdoor pool
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is ￥20,830
￥23,747 total
includes taxes & fees
Dec 28 - Dec 29
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 Sherwood Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Very nice hotel. The dog park could have better lighting. "
Andrew 1-night trip
Posted 4 days ago
Graduate by Hilton Annapolis

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Frequently asked questions

What are some accommodations with pools in Sherwood?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Features 2 outdoor pools, a children's pool, and a private beach. Hilton Garden Inn Annapolis Downtown: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool, and a snack bar/deli. Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wired internet access.
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.