Hotels with Swimming Pool in Chesapeake Beach, Maryland

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Check availability on Chesapeake Beach Hotels with Swimming Pool

Our top choices for Chesapeake Beach hotels with a pool

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
"Pool is also now open!"
United States
Tatiana
The price is P8,259
P10,400 total
includes taxes & fees
May 25 - May 26
Rod 'N' Reel Resort

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    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."
United States
Michael
The price is P7,987
P8,785 total
includes taxes & fees
Jun 2 - Jun 3
St Michaels Inn

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick
3.0 star property
Prince Frederick
8.6 out of 10, Excellent, (955 reviews)
  • cleanliness
    Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.
"Pool and hot tub were clean."
United States
Jenny
The price is P7,277
P8,077 total
includes taxes & fees
Jun 21 - Jun 22
Springhill Suites by Marriott Prince Frederick

Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
3.0 star property
Solomons
8.6 out of 10, Excellent, (665 reviews)
  • cleanliness
    Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
"The on site bar and pool are great!"
United States
Aaron
The price is P8,249
P9,156 total
includes taxes & fees
Jun 15 - Jun 16
Hilton Garden Inn Solomons

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, (719 reviews)
  • cleanliness
    Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.
"pool was in good condition"
United States
Jessica
The price is P7,036
P8,495 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express Prince Frederick by IHG

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    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"
United States
Emily
The price is P5,987
P6,825 total
includes taxes & fees
May 28 - May 29
Sonesta ES Suites Annapolis

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (134 reviews)
  • cleanliness
    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. "
United States
Katie
The price is P11,726
P12,899 total
includes taxes & fees
May 26 - May 27
Parsonage Inn

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (134 reviews)
  • cleanliness
    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."
United States
JAMES
The price is P16,046
P17,651 total
includes taxes & fees
May 28 - May 29
The Tilghman Island Inn

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (486 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
"Can not wait to come back in the summer and enjoy the pool and Boathouse Bar!"
United States
June
The price is P14,444
P16,466 total
includes taxes & fees
May 27 - May 28
Anchored Inn at Hidden Harbour Marina
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.

Choose what matters most at hotels with a pool in Chesapeake Beach

Top Chesapeake Beach Hotel Reviews

Frequently asked questions

What are some hotels with pools in Chesapeake Beach?
Rod 'N' Reel Resort: Hotel, 1-minute walk from Chesapeake Bay. 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: Offers a snack bar/deli, an indoor pool, and daily. Econo Lodge Andrews Air Force Base: Features a full-service spa, an outdoor pool, and 2 bars. SpringHill Suites by Marriott Annapolis: Offers daily, a seasonal outdoor pool, and free self parking.
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.

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