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

Chesapeake Beach Hotels with Swimming Pool

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Check availability on Chesapeake Beach Hotels with Swimming Pools

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern bar area with a long counter and multiple bar stools.

1. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
  • Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
RM591
RM656 total
includes taxes & fees
20 Oct - 21 Oct
Rod 'N' Reel Resort
A swimming pool with blue lounge chairs and a building with balconies in the background.
A modern kitchen with a large island, bar stools, and a wine rack.
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.
A black Mercedes-Benz SUV parked in front of a building with a sign that reads "Anchored Inn at Hidden Harbour Marina."

2. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
  • Pool paradise meets scenic marina views for a refreshing escape on the water.
RM758
RM864 total
includes taxes & fees
13 Oct - 14 Oct
Anchored Inn at Hidden Harbour Marina
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.
A hotel lobby with multiple seating areas, including tables and chairs, a television mounted on the wall, and a kitchen area in the background.
A hotel with a brick facade, a covered entrance, and a sign reading "Springhill Suites."
A hotel lobby with a reception desk, a glass-top table with a bowl, potted plants, a vending machine, and a large window.

3. Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick
Prince Frederick
  • Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.
RM483
RM536 total
includes taxes & fees
18 Oct - 19 Oct
Springhill Suites by Marriott Prince Frederick
A swimming pool with clear water, surrounded by walls with arched windows and a tiled floor.
A bathroom with a granite countertop sink, a large mirror, a shower with grab bars, and a white bathtub.
A hotel room with a large bed, bedside tables, a desk, a chair, a flat-screen TV, and a window with a view.
A Holiday Inn Express hotel with a brick facade, a central entrance, and a parking lot with several cars.

4. Holiday Inn Express Prince Frederick by IHG

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.
RM502
RM603 total
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Express Prince Frederick by IHG
A swimming pool with multiple people swimming and lounging around.
A waterfront property with houses, a dock, and a grassy area.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.
A building with a sign reading "The Inn."

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
RM613
RM674 total
includes taxes & fees
13 Oct - 14 Oct
Knapps Narrows Marina & Inn
A pool with two Adirondack chairs and a basket of items on the grass.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.
A hot tub in a grassy area with a building in the background.

6. The Inn at Tacaro Estate

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.
RM1,429
RM1,629 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Tacaro Estate
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A spacious indoor dining area with large windows, tables, and chairs.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

7. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
RM756
RM831 total
includes taxes & fees
19 Oct - 20 Oct
The Tilghman Island Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.
A waterfront hotel with a covered dock and a large building with multiple balconies.
A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.

8. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
RM993
RM1,296 total
includes taxes & fees
18 Oct - 19 Oct
Wylder Tilghman Island
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.
A room with a view of a wooden deck and a gazebo by the water.

9. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
RM2,096
RM2,305 total
includes taxes & fees
8 Nov - 9 Nov
Inn at Perry Cabin
A swimming pool with lounge chairs and a fence.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.
A gym with treadmills, weight machines, and dumbbells.

10. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
  • Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.
RM372
RM424 total
includes taxes & fees
1 Nov - 2 Nov
Sonesta ES Suites Annapolis
View all properties

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

Breakfast included
Hot tub
5 stars
4 stars
Spa

Top Chesapeake Beach Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 4 hours ago
Sonesta ES Suites Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"na"
Jeffrey 2-night trip
Posted 6 hours ago
St Michaels Inn
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Beautiful property on the Chesapeake Bay. It was very clean. We went off season highly recommend."
Melissa 2-night trip
Posted 6 hours ago
Rod 'N' Reel Resort
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"The first person that greets you sets your entire stay and Dannielle is an amazing person to have at the front desk. Happy, knowledgeable and referred us to a delicious nearby restaurant for some weary travelers. And you know if a staff member makes such an impression that you make sure you get the correct spelling of their name. Rooms were super clean too!"
Cherylene 1-night trip
Posted 7 hours ago
SpringHill Suites by Marriott Annapolis
Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf

10/10 Excellent
"Clean & comfy room. Nice staff."
Alicia 6-night trip
Posted 3 days ago
Residence Inn by Marriott Waldorf

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, visit 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 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 24Β°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 5Β°C.

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