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

Hotels with Swimming Pools in Chesapeake Beach

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Check availability on Chesapeake Beach Hotels with Swimming Pools

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 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 gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
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.

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.
S$189
includes taxes & fees
25 Oct - 26 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 hotel lobby with a reception desk, a glass-top table with a bowl, potted plants, a vending machine, and a large window.
A lobby with two yellow armchairs, a glass-top coffee table, a lamp, and a decorative bamboo wall.

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.
S$168
includes taxes & fees
20 Oct - 21 Oct
Springhill Suites by Marriott Prince Frederick
A swimming pool with clear water, surrounded by walls with arched windows and a tiled floor.
A Holiday Inn Express hotel with a brick facade, a central entrance, and a parking lot with several cars.
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.

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.
S$182
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Prince Frederick by IHG
A swimming pool with blue lounge chairs and a building with balconies in the background.
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."
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.
S$271
includes taxes & fees
12 Nov - 13 Nov
Anchored Inn at Hidden Harbour Marina
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
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.

5. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
S$261
includes taxes & fees
19 Oct - 20 Oct
The Tilghman Island Inn
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."

6. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
S$211
includes taxes & fees
1 Nov - 2 Nov
Knapps Narrows Marina & Inn
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 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.

7. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
S$356
includes taxes & fees
18 Oct - 19 Oct
Wylder Tilghman Island
A pool with two Adirondack chairs and a basket of items on the grass.
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.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.

8. 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.
S$497
includes taxes & fees
15 Nov - 16 Nov
The Inn at Tacaro Estate
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A hotel room with two beds, a chair, and a painting on the wall.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

9. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
S$113
includes taxes & fees
1 Nov - 2 Nov
St Michaels Inn
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 hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

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.
S$138
includes taxes & fees
9 Nov - 10 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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Great rooom, really great service."
Brandon 1-night trip
Posted 3 hours ago
Rod 'N' Reel Resort
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Stay was exceptional!!"
Kaiya 1-night trip
Posted 23 hours ago
SpringHill Suites by Marriott Annapolis
Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

10/10 Excellent
"Everything and everyone was nice. The room was very clean and the breakfast was by far the best I have had."
Heather 4-night trip
Posted 1 day ago
Holiday Inn Express Waldorf by IHG
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

8/10 Good
"Rooms clean staff very 👍 nice"
Martone 1-night trip
Posted 1 day ago
Springhill Suites by Marriott Prince Frederick
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 3 days 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 4 days ago
Sonesta ES Suites Annapolis
Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf

10/10 Excellent
"Clean & comfy room. Nice staff."
Alicia 6-night trip
Posted 7 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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