A harbor with boats docked, a pier, and a row of houses along the water.

Chesapeake Beach Hotel Guide - Hotels with Pool in Chesapeake Beach, Maryland

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Check availability on Chesapeake Beach Hotels with Pool

Our top choices for Chesapeake Beach hotels with a pool

Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is €215
includes taxes & fees
28 Jul - 29 Jul
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, (1,000 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is €95
includes taxes & fees
21 Jul - 22 Jul
St Michaels Inn
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, (739 reviews)
  • cleanliness
    Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.
The price is €107
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Prince Frederick by IHG
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (388 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is €145
includes taxes & fees
23 Jul - 24 Jul
Knapps Narrows Marina & Inn
Outdoor pool

Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
3.0 star property
Solomons
8.6 out of 10, Excellent, (686 reviews)
  • cleanliness
    Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
The price is €127
includes taxes & fees
13 Aug - 14 Aug
Hilton Garden Inn Solomons
Front of property

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (143 reviews)
  • cleanliness
    Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
The price is €217
includes taxes & fees
10 Aug - 11 Aug
The Tilghman Island Inn
Indoor pool

Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG
2.5 star property
Waldorf
8.2 out of 10, Very good, (1,005 reviews)
  • cleanliness
    Dive into poolside relaxation at this colonial-style hotel, where free cabanas add luxury to the indoor swimming experience.
The price is €107
includes taxes & fees
19 Jul - 20 Jul
Holiday Inn Express Waldorf by IHG
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, (491 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is €234
includes taxes & fees
2 Aug - 3 Aug
Anchored Inn at Hidden Harbour Marina
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (75 reviews)
  • cleanliness
    Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
The price is €204
includes taxes & fees
22 Jul - 23 Jul
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.
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Choose what matters most at hotels with a pool in Chesapeake Beach

Breakfast included
Hot tub

Top Chesapeake Beach Hotel Reviews

Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

10/10 Excellent
"The room was clean, breakfast was good and hot employees were helpful and pleasant and the property was clean."
Jonathan 2-night trip
Posted 3 hours ago
Holiday Inn Express Waldorf by IHG

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. St Michaels Inn: Offers daily, a seasonal outdoor pool and free self parking. Econo Lodge Andrews Air Force Base: Offers a full-service spa, an outdoor pool and 2 bars. Spark by Hilton Waldorf: Features buffet, a seasonal outdoor pool and complimentary wireless Internet access. Inn at Perry Cabin: Offers 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 such as Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. During your stay, visit sights such as Rod n Reel Charter Fishing, Breezy Point Beach and Northern Chesapeake Bay. 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 accommodation that offers an outdoor pool if you're planning to visit Chesapeake Beach in the hottest months of July, August or June, when the average temperature is 24°C. Accommodation with an indoor pool may be what you want if you visit during the coldest months of January, February or December, when the average temperature is 5°C.