Hotels with Swimming Pool in Chesapeake Beach, Maryland
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Our top choices for Chesapeake Beach hotels with a pool
8.6 out of 10, Excellent, (1,001 reviews)
- Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
"Pool is also now open!"
Tatiana
The price is P8,259
P10,400 total
includes taxes & fees
May 25 - May 26
8.2 out of 10, Very Good, (1,000 reviews)
- Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
"In the warmer months you can enjoy the pool and roomy outdoor seating areas."
Michael
The price is P7,987
P8,785 total
includes taxes & fees
Jun 2 - Jun 3
Springhill Suites by Marriott Prince Frederick
Springhill Suites by Marriott Prince FrederickPrince Frederick
8.6 out of 10, Excellent, (955 reviews)
- Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.
"Pool and hot tub were clean."
Jenny
The price is P7,277
P8,077 total
includes taxes & fees
Jun 21 - Jun 22
8.6 out of 10, Excellent, (665 reviews)
- Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
"The on site bar and pool are great!"
Aaron
The price is P8,249
P9,156 total
includes taxes & fees
Jun 15 - Jun 16
Holiday Inn Express Prince Frederick by IHG
Holiday Inn Express Prince Frederick by IHGPrince Frederick
8.8 out of 10, Excellent, (719 reviews)
- Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.
"pool was in good condition"
Jessica
The price is P7,036
P8,495 total
includes taxes & fees
Jun 14 - Jun 15
8.8 out of 10, Excellent, (1,004 reviews)
- Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness center.
"Only stayed for two nights but I plan to come back to this location for any long stays The kitchen area was stocked with essentials and there is a CVS walkable to get supplies for eating in The breakfast is a full variety with a friendly atmosphere So many little areas to make the stay more like home or even resort like with a little fire pit area small pool and basketball court Easy to entertain kids in warmer months HUGE tv and comfy bed"
Emily
The price is P5,987
P6,825 total
includes taxes & fees
May 28 - May 29
9.2 out of 10, Wonderful, (134 reviews)
- Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons.
"We really enjoyed our stay at The Parsonage. The property and room were kept well. The staff were sweet and attentive. Very good location as far as walking distance to shops, restaurants and the waterfront area. I would certainly return and certainly recommend to anyone visiting St. Michael’s. "
Katie
The price is P11,726
P12,899 total
includes taxes & fees
May 26 - May 27
9.6 out of 10, Exceptional, (134 reviews)
- Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
"We had a wonderful dinner at the adjoining restaurant on our first night, loved the beautiful views from our room, enjoyed walks all over Tilghman, swam in the pool, and did a lot of relaxing."
JAMES
The price is P16,046
P17,651 total
includes taxes & fees
May 28 - May 29
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.
Top Chesapeake Beach Hotel Reviews
Sonesta ES Suites Annapolis
10/10 Excellent
