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Find Hotels with a Pool in Chesapeake Beach, MD

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Check availability on Chesapeake Beach Hotels with a Pool

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

Top Chesapeake Beach 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 SAR 391
SAR 510 total
includes taxes & fees
4 Dec - 5 Dec
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
The price is SAR 388
SAR 427 total
includes taxes & fees
23 Dec - 24 Dec
St Michaels Inn
Outdoor pool
Inn at Perry Cabin

Inn at Perry Cabin

5.0 star property
St. Michaels
9.6 out of 10, Exceptional, (370)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is SAR 1,354
SAR 1,638 total
includes taxes & fees
4 Dec - 5 Dec
Inn at Perry Cabin
Porch
Parsonage Inn

Parsonage Inn

3.5 star property
St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is SAR 751
SAR 826 total
includes taxes & fees
1 Jan - 2 January 2026
Parsonage Inn
Exterior
George Brooks House B&B

George Brooks House B&B

3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is SAR 638
SAR 702 total
includes taxes & fees
1 Jan - 2 January 2026
George Brooks House B&B
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 SAR 450
SAR 495 total
includes taxes & fees
7 Dec - 8 Dec
Knapps Narrows Marina & Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
8.8 out of 10, Excellent, (89)
"Very relaxing stay."
United States
Anne
The price is SAR 450
SAR 661 total
includes taxes & fees
1 Jan - 2 January 2026
Wylder Tilghman Island
Seasonal outdoor pool, pool umbrellas
The Tilghman Island Inn

The Tilghman Island Inn

3.5 star property
Tilghman
9.6 out of 10, Exceptional, (119)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is SAR 751
SAR 826 total
includes taxes & fees
7 Dec - 8 Dec
The Tilghman Island Inn
Outdoor pool
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

3.0 star property
Solomons
8.6 out of 10, Excellent, (637)
"Was a great and pleasant experience "
United States
MARLON
The price is SAR 431
SAR 478 total
includes taxes & fees
11 Dec - 12 Dec
Hilton Garden Inn Solomons
Indoor pool
Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

2.5 star property
Prince Frederick
8.8 out of 10, Excellent, (688)
"Loved it"
United States
Francisco
The price is SAR 387
SAR 430 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Prince Frederick by IHG
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 Chesapeake Beach Hotel Reviews

Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

10/10 Excellent
"Loved it"
Francisco 2-night trip
Posted 4 days ago
Holiday Inn Express Prince Frederick by IHG

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Frequently asked questions

What are some hotels with pools in Chesapeake Beach?
Rod 'N' Reel Resort: Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Spark by Hilton Waldorf: Features daily, a seasonal outdoor pool, and free self parking. St Michaels Inn: Features a snack bar/deli, a seasonal outdoor pool, and full. Candlewood Suites Annapolis by IHG: Provides a snack bar/deli, an indoor pool, and daily.
What is there to see and do in Chesapeake Beach?
Make a point to visit attractions like Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. During your stay, check out sights such as Rod n Reel Charter Fishing, Bruce Gabrielson's Surf Art Gallery and Museum, and Breezy Point Beach. The beaches and restaurants are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Chesapeake Beach?
You may want to consider an accommodation with an outdoor swimming pool if you plan to visit Chesapeake Beach in the hottest months of July, August, or June when the average temperature is 75°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temperature is 40°F.