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Find hotels with pools in Oyster Harbor, Annapolis from $87

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Check availability on Oyster Harbor Hotels with a Pool

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Dec 5 - Dec 6
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Dec 12 - Dec 14

Top Oyster Harbor Hotels with a Pool

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
$163 nightly
The price is $177
Dec 7 - Dec 8
Total with taxes and fees
Kent Island 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
$79 nightly
The price is $88
Dec 7 - Dec 8
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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
$138 nightly
The price is $151
Jan 2 - Jan 3, 2026
Total with taxes and fees
Rod 'N' Reel Resort
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
$107 nightly
The price is $118
Dec 14 - Dec 15
Total with taxes and fees
St Michaels 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
$100 nightly
The price is $110
Dec 5 - Dec 6
Total with taxes and fees
Knapps Narrows Marina & 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
$85 nightly
The price is $94
Dec 7 - Dec 8
Total with taxes and fees
Quality 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, (1002)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
Indoor pool, sun loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (670)
"Great view, good ambiance all around"
United States
Dianne
$116 nightly
The price is $129
Dec 7 - Dec 8
Total with taxes and fees
Hyatt Place Kent Narrows & 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
$146 nightly
The price is $167
Dec 31 - Jan 1, 2026
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
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
$78 nightly
The price is $87
Dec 7 - Dec 8
Total with taxes and fees
Best Western Kent Narrows 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 Oyster Harbor Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great Hotel, Amazing location, very clean, everyone is friendly and helpful. Always recommend staying here if you are in Annapolis"
Tatiana 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

What are some hotels with pools in Oyster Harbor?
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: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Offers buffet, an indoor pool, and free self parking. Microtel Inn & Suites by Wyndham Gambrills: Features buffet, a seasonal outdoor pool, and free self parking. Hilton Garden Inn Annapolis Downtown: 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 Oyster Harbor?
The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay showcase the area's natural beauty. Discover sights such as Bay Ridge Beach, Maryland Quiet Waters Park, and Annapolis Landing Marina during your stay.
When is the best time to book a hotel with a pool in Oyster Harbor?
You may want to consider a place to stay that offers an outdoor if you're planning to visit in the warmest months of July, August, or June when the average temperature is 75°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temperature is 40°F.

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