Sherwood Hotels with Swimming Pool

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Check availability on Sherwood Hotels with Swimming Pools

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Sherwood Hotels with Swimming Pools

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

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 RM327
RM363 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)
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 RM401
RM528 total
includes taxes & fees
4 Jan - 5 Jan 2026
Rod 'N' Reel Resort
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (127)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is RM444
RM634 total
includes taxes & fees
9 Dec - 10 Dec
Kent Island Resort
Indoor pool, pool loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (668)
"Great view, good ambiance all around"
United States
Dianne
The price is RM478
RM530 total
includes taxes & fees
29 Dec - 30 Dec
Hyatt Place Kent Narrows & Marina
Indoor pool, open 5 AM to 11 PM, pool loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is RM426
RM473 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
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 RM552
RM629 total
includes taxes & fees
1 Jan - 2 Jan 2026
Anchored Inn at Hidden Harbour Marina
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 RM459
RM504 total
includes taxes & fees
7 Dec - 8 Dec
St Michaels Inn
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.0 out of 10, Very good, (1001)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is RM346
RM384 total
includes taxes & fees
10 Dec - 11 Dec
Best Western Kent Narrows 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 RM333
RM366 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (858)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is RM351
RM389 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Rodger is awesome! Chef is great too "
Scott 6-night trip
Posted 4 days ago
DoubleTree by Hilton Hotel Annapolis

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Frequently asked questions

What are some accommodation options 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 swimming 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 high-speed (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 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.