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

Hotels with Swimming Pool in Chesapeake Beach, Maryland

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Check availability on Chesapeake Beach Hotels with Swimming Pool

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

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 modern bar area with a long counter and multiple bar stools.
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.
P9,044
P10,039 total
includes taxes & fees
Oct 20 - Oct 21
Rod 'N' Reel Resort
A swimming pool with blue lounge chairs and a building with balconies in the background.
A marina with docked boats, a picnic area, and a grassy lawn with a tree.
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.
A modern kitchen with a large island, bar stools, and a wine rack.

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.
P12,462
P14,207 total
includes taxes & fees
Oct 7 - Oct 8
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 lobby with a reception desk, a glass-top table with a bowl, potted plants, a vending machine, and a large window.
A hotel with a brick facade, a covered entrance, and a sign reading "Springhill Suites."

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.
P7,391
P8,203 total
includes taxes & fees
Oct 25 - Oct 26
Springhill Suites by Marriott Prince Frederick
A swimming pool with clear water, surrounded by walls with arched windows and a tiled floor.
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.
A bathroom with a granite countertop sink, a large mirror, a shower with grab bars, and a white bathtub.

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.
P7,381
P8,887 total
includes taxes & fees
Oct 11 - Oct 12
Holiday Inn Express Prince Frederick by IHG
A swimming pool with multiple people swimming and lounging around.
A covered patio area with wicker furniture and a view of a building with large windows.
A building with a sign reading "The Inn."
A waterfront property with houses, a dock, and a grassy area.

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
P6,255
P6,881 total
includes taxes & fees
Nov 1 - Nov 2
Knapps Narrows Marina & Inn
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.
A large building with a swimming pool, dock, and green surroundings.

6. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
P11,572
P12,729 total
includes taxes & fees
Oct 5 - Oct 6
The Tilghman Island 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 cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A hot tub in a grassy area with a building in the background.

7. 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.
P21,883
P24,946 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Tacaro Estate
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 waterfront property with a covered patio, a dock, and a boat.

8. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
P13,680
P18,176 total
includes taxes & fees
Oct 18 - Oct 19
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 hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

9. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
  • Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness center.
P5,692
P6,489 total
includes taxes & fees
Nov 1 - Nov 2
Sonesta ES Suites Annapolis
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
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.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.

10. 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.
P32,089
P35,298 total
includes taxes & fees
Oct 26 - Oct 27
Inn at Perry Cabin
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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
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 3 days ago
St Michaels Inn
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Nice room and bed. Love that they had continental breakfast"
Italo 1-night trip
Posted 5 days ago
SpringHill Suites by Marriott Annapolis
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."
Christina 2-night trip
Posted 5 days ago
Inn at Perry Cabin

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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