Book the Best Hotels with POOL in Chesapeake Beach in 2026 | Expedia.ca

Aerial view of Chesapeake Beach marina with luxury sail boats, beach house apartments, fishing boats near the water park popular vacation spot for Washington residents in Calvery county Maryland

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Check availability on Chesapeake Beach Hotels with a Pool

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Jun 12 - Jun 14

Our top choices for Chesapeake Beach hotels with a pool

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

Rod 'N' Reel Resort

Chesapeake Beach

Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.

CA $252 total

includes taxes & fees

Jun 23 - Jun 24

Indoor pool

Holiday Inn Express Prince Frederick by IHG

Prince Frederick

Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.

CA $197 total

includes taxes & fees

Jun 14 - Jun 15

Outdoor pool

Hilton Garden Inn Solomons

Solomons

Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.

CA $211 total

includes taxes & fees

Jun 14 - Jun 15

Indoor pool

Springhill Suites by Marriott Prince Frederick

Prince Frederick

Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.

CA $188 total

includes taxes & fees

Jun 17 - Jun 18

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St. Michaels

Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.

CA $192 total

includes taxes & fees

Jun 10 - Jun 11

Seasonal outdoor pool

Knapps Narrows Marina & Inn

Sherwood

Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.

CA $228 total

includes taxes & fees

Jun 4 - Jun 5

Seasonal outdoor pool

Sonesta ES Suites Annapolis

Edgewater

Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.

CA $169 total

includes taxes & fees

Jun 7 - Jun 8

Indoor pool

Courtyard Marriott Waldorf

Waldorf

Aquatic retreat awaits with indoor pool and hot tub for relaxation after a day out.

CA $178 total

includes taxes & fees

Jun 10 - Jun 11

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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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent

"Nice property with beautiful views of the Chesapeake Bay."

Courtyard Marriott Waldorf

Courtyard Marriott Waldorf

4/10 Poor

"Property did not meet expectations. Room was very awkward with TV viewed from the side of bed not the foot. Bath tub was extremely small. Window ledges were extremely dirty. Light from hallway was very visible in the room. Not very sound-proof. Noisy hallway. Toilet was extremely low. Few tissues were left in box and when used asked for replacement but was told they needed the empty box before a replacement was given. Pool was not available but was not made aware of this until after check-in. Overall was not a good experience."

Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

2/10 Terrible

"I had requested a walk-in shower over the phone prior to arriving at hotel and again at check-in because of my knee and both times was assured the room had one. Upon entering the room I found out there was a tub so I immediately went back to registration to ask if I could get another room and was then told there were no rooms with walk-in showers. The receptionist apologized and stated all she could do was refund my money and I could go somewhere else. I wasn't about to go searching all over Waldorf to find another place to stay so I figured at least I could go swimming in the indoor pool. Wrong, the water was ice cold, the concrete around the pool was all cracked up and the handrail was very unsafe! I will say the rooms weren't too bad other than the shower but overall I was very disappointed in my stay."

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

6/10 Okay

"Carpet was old and needed replacement and cleaning. Quite smelly Once I mentioned to the front desk, they got maintenance on it and reported it to corporate. Needs some updates. Could not use the gym or pool area Gym smelled bad not cleaned though lots of housekeeping around and the pool water was and hot tub were merky. It was also insane that they were charging for unsecured parking that used to be free."

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 daily, a seasonal outdoor pool, and free self parking. Econo Lodge Andrews Air Force Base: Features a full-service spa, an outdoor pool, and 2 bars. St Michaels Inn: 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, 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 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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