Photo by Ronanne Vinson

Find Hotels with a Pool in Chesapeake Beach, MD

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Beach Hotels with a Pool

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Chesapeake Beach hotels with a pool

Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
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 ￥14,213
￥18,898 total
includes taxes & fees
Jan 3 - Jan 4, 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 ￥15,546
￥17,101 total
includes taxes & fees
Jan 4 - Jan 5, 2026
St Michaels 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 ￥18,396
￥27,104 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Wylder Tilghman Island
Indoor pool
Holiday Inn Express Prince Frederick by IHG

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, (695)
"Great environment, friendly staff, great place to stay with family and lots of things to do around the area!"
United States
Rosemary
The price is ￥16,080
￥19,582 total
includes taxes & fees
Dec 28 - Dec 29
Holiday Inn Express Prince Frederick 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 ￥18,734
￥20,607 total
includes taxes & fees
Dec 27 - Dec 28
Knapps Narrows Marina & Inn
Indoor pool
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick
3.0 star property
Prince Frederick
8.6 out of 10, Excellent, (938)
"Everything was perfect, from the room and staff and the breakfast"
United States
Louise
The price is ￥15,234
￥16,909 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Springhill Suites by Marriott Prince Frederick
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, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is ￥20,936
￥23,868 total
includes taxes & fees
Dec 28 - Dec 29
Anchored Inn at Hidden Harbour Marina
Outdoor pool
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
3.0 star property
Solomons
8.6 out of 10, Excellent, (641)
"Was a great and pleasant experience "
United States
MARLON
The price is ￥17,912
￥19,882 total
includes taxes & fees
Dec 30 - Dec 31
Hilton Garden Inn Solomons
Seasonal outdoor pool
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (966)
"Clean, spacious, quiet, convenient location. I’d stay there again. "
United States
Michael
The price is ￥14,363
￥16,373 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Sonesta ES Suites Annapolis
Exterior
George Brooks House B&B

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 ￥23,886
￥26,275 total
includes taxes & fees
Jan 1 - Jan 2, 2026
George Brooks House B&B
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.
View all properties

Top Chesapeake Beach Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Everything was great! The desk receptionists were especially awesome. Loved the restaurants they recommended, spot on."
Catherine 2-night trip
Posted 10 days ago
St Michaels Inn

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. Spark by Hilton Waldorf: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. Sonesta ES Suites Annapolis: Features a snack bar/deli, a seasonal outdoor pool, and full. Residence Inn by Marriott Waldorf: Offers a snack bar/deli, an indoor pool, and daily. SpringHill Suites by Marriott Annapolis: Provides a snack bar/deli, an indoor pool, and full.
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.