Book the Best Hotels with POOL in Chesapeake Beach in 2026

Q: 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. Sonesta ES Suites Annapolis : Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. Holiday Inn Express Waldorf by IHG : Features buffet, an indoor pool, and free self parking. SpringHill Suites by Marriott Annapolis : Offers a snack bar/deli, an indoor pool, and daily.

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

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Our top choices for Chesapeake Beach hotels with a pool

A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.

1. Rod 'N' Reel Resort

Chesapeake Beach

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

CA $249 total

includes taxes & fees

Nov 8 - Nov 9

An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.

2. Springhill Suites by Marriott Prince Frederick

Prince Frederick

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

CA $184 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with clear blue water, surrounded by sunlit arched windows and a row of chairs.

3. 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 $199 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with blue lounge chairs and a building with balconies in the background.

4. Anchored Inn at Hidden Harbour Marina

Deale

Pool paradise meets scenic marina views for a refreshing escape on the water.

CA $257 total

includes taxes & fees

Nov 29 - Nov 30

A swimming pool with multiple people swimming and lounging around.

5. Knapps Narrows Marina & Inn

Sherwood

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

CA $200 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with a wooden deck, lounge chairs, and a fenced area.

6. The Tilghman Island Inn

Tilghman

Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.

CA $423 total

includes taxes & fees

Oct 31 - Nov 1

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

7. St Michaels Inn

St. Michaels

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

CA $117 total

includes taxes & fees

Nov 29 - Nov 30

A pool with two Adirondack chairs and a basket of items on the grass.

8. The Inn at Tacaro Estate

Tracys Landing

Escape to a seasonal outdoor paradise with a hot tub and 24-hour pool access at this luxury bed & breakfast.

CA $558 total

includes taxes & fees

Nov 2 - Nov 3

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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

St Michaels Inn

10/10 Excellent

"Our stay was much better than I was expecting! The area was very quiet and the staff friendly and helpful. Continental breakfast was your standard fare and everything clean."

Residence Inn by Marriott Waldorf

8/10 Good

"Didn't like the one hour wait to get the room...it was well after 5 to be assigned a room....the television in the common area of the room didn't work and staff was notified but no one came to fix it. The fire alarm went off early am and had to get up and the rowdy guess...well the police was there for them several times throughout the night."

Springhill Suites by Marriott Prince Frederick

10/10 Excellent

"The only think I would change is the coffee to one of the more modern automatic types and maybe add flavored creamer. The room coffee maker is older and they only provide a powder packet. I brought my own but the hotel was nice and I would sty again."

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. Sonesta ES Suites Annapolis: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. Holiday Inn Express Waldorf by IHG: Features buffet, an indoor pool, and free self parking. SpringHill Suites by Marriott Annapolis: Offers a snack bar/deli, an indoor pool, and daily.

What is there to see and do in Chesapeake Beach?

Enjoy a stroll along the shore at Breezy Point Beach and Brownies Beach. During your stay, check out sights such as Chesapeake Beach Water Park, Chesapeake Beach Railway Museum, and Rod n Reel Charter Fishing. 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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