Search Hotels with Pool in Sherwood

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Check availability on Sherwood Hotels with Pool

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Sherwood 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, (1002)
"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 ฿2,829
฿3,761 total
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
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, (1000)
"Staff was friendly, courteous, and helpful."
United States
Donna
The price is ฿3,122
฿3,434 total
includes taxes & fees
7 Jan - 8 Jan 2026
St Michaels Inn
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, (939)
"It was very comfortable and clean"
United States
Maria
The price is ฿2,455
฿2,725 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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 ฿3,724
฿4,097 total
includes taxes & fees
29 Dec - 30 Dec
Knapps Narrows Marina & Inn
Seasonal outdoor pool
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (828)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ฿2,638
฿2,902 total
includes taxes & fees
7 Jan - 8 Jan 2026
Quality Inn
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 ฿3,662
฿5,395 total
includes taxes & fees
12 Jan - 13 Jan 2026
Wylder Tilghman Island
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 ฿2,615
฿2,902 total
includes taxes & fees
19 Jan - 20 Jan 2026
Quality Inn Grasonville near Kent 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, (1002)
"Nice place "
United States
Tucker T
The price is ฿2,592
฿2,877 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Kent Narrows 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 ฿3,808
฿5,311 total
includes taxes & fees
28 Dec - 29 Dec
Kent Island Resort
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, (471)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is ฿4,162
฿4,745 total
includes taxes & fees
29 Dec - 30 Dec
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Clean and friendly staff"
Lisa 2-night trip
Posted 10 days ago
Hilton Garden Inn Kent Island Marina

Frequently asked questions

What are some accommodation options with pools in Sherwood?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. Historic Inns of Annapolis: Offers 2 outdoor swimming pools, a children's pool and a private beach. Crowne Plaza Annapolis by IHG: Provides buffet, a seasonal outdoor pool and complimentary high-speed (wired) Internet access. Graduate by Hilton Annapolis: Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool and a snack bar/deli. Hilton Garden Inn Annapolis Downtown: Offers buffet, a seasonal outdoor pool and complimentary wireless 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 with an outdoor swimming pool if you're planning to visit Sherwood in the warmest months of July, August or June, when the average temperature is 24°C. Accommodation offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temperature is 5°C.