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

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Check availability on Chesapeake Beach Hotels with Pool

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 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 modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

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.
฿4,848
฿5,381 total
includes taxes & fees
21 Oct - 22 Oct
Rod 'N' Reel Resort
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 lobby with two yellow armchairs, a glass-top coffee table, a lamp, and a decorative bamboo wall.
A hotel lobby with a reception desk, a glass-top table with a bowl, potted plants, a vending machine, and a large window.

2. 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.
฿3,962
฿4,397 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 coffee station with two espresso machines, a coffee grinder, and various coffee-related items.
A Holiday Inn Express hotel with a brick facade, a central entrance, and a parking lot with several cars.

3. 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.
฿3,733
฿4,517 total
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Prince Frederick by IHG
A swimming pool with blue lounge chairs and a building with balconies 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."
A modern kitchen with a large island, bar stools, and a wine rack.
A marina with docked boats, a picnic area, and a grassy lawn with a tree.

4. 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.
฿6,219
฿7,090 total
includes taxes & fees
19 Oct - 20 Oct
Anchored Inn at Hidden Harbour Marina
A swimming pool with multiple people swimming and lounging around.
A building with a sign reading "The Inn."
A covered patio area with wicker furniture and a view of a building with large windows.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
฿5,030
฿5,532 total
includes taxes & fees
25 Oct - 26 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 hot tub in a grassy area with a building in the background.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

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.
฿11,730
฿13,372 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 large building with a swimming pool, dock, and green surroundings.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A modern lounge area with a fireplace, seating, and a view of the outdoors.

7. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
฿6,203
฿6,823 total
includes taxes & fees
19 Oct - 20 Oct
The Tilghman Island Inn
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.
A white house with a garden patio featuring a wicker chair and a round table.
A room with a view of a wooden deck and a gazebo by the water.

8. 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.
฿17,253
฿18,979 total
includes taxes & fees
8 Nov - 9 Nov
Inn at Perry Cabin
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A waterfront property with a covered patio, a dock, and a boat.
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.

9. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
฿8,148
฿10,639 total
includes taxes & fees
18 Oct - 19 Oct
Wylder Tilghman Island
A swimming pool with lounge chairs and a fence.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A gym with treadmills, weight machines, and dumbbells.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

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.
฿3,051
฿3,478 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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 2 hours ago
St Michaels Inn
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 1 day ago
Sonesta ES Suites Annapolis
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 1 day 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 1 day 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 4 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 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.

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