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 a Pool

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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.
₩197,394
₩264,571 total
includes taxes & fees
Oct 7 - Oct 8
Rod 'N' Reel Resort
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.
A lobby with two yellow armchairs, a glass-top coffee table, a lamp, and a decorative bamboo wall.
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."

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.
₩161,389
₩179,141 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 bathroom with a granite countertop sink, a large mirror, a shower with grab bars, and a white bathtub.
A Holiday Inn Express hotel with a brick facade, a central entrance, and a parking lot with several cars.
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.
₩161,100
₩193,975 total
includes taxes & fees
Oct 4 - Oct 5
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 docked boats, a picnic area, and a grassy lawn with a tree.
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.

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.
₩281,526
₩320,948 total
includes taxes & fees
Sep 30 - Oct 1
Anchored Inn at Hidden Harbour Marina
A swimming pool with multiple people swimming and lounging around.
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."
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.
₩204,788
₩225,267 total
includes taxes & fees
Sep 28 - Sep 29
Knapps Narrows Marina & Inn
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 conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

6. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
₩121,644
₩133,809 total
includes taxes & fees
Oct 1 - Oct 2
St Michaels Inn
A swimming pool with lounge chairs and a fence.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A gym with treadmills, weight machines, and dumbbells.

7. 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.
₩132,293
₩150,806 total
includes taxes & fees
Sep 28 - Sep 29
Sonesta ES Suites Annapolis
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A large building with a swimming pool, dock, and green surroundings.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
A spacious indoor dining area with large windows, tables, and chairs.

8. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
₩252,571
₩277,828 total
includes taxes & fees
Sep 27 - Sep 28
The Tilghman Island Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.
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.

9. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
₩230,508
₩321,858 total
includes taxes & fees
Sep 27 - Sep 28
Wylder Tilghman Island
A swimming pool with lounge chairs and a door.
A Courtyard Marriott hotel with a fire pit in the courtyard, outdoor seating, and a brick facade.
A hotel room with two beds, a desk, a chair, a large window with curtains, and a painting on the wall.
A Courtyard Marriott hotel entrance with a covered walkway, multiple windows, and a well-lit facade.

10. Courtyard Marriott Waldorf

Courtyard Marriott Waldorf
Waldorf
  • Aquatic retreat awaits with indoor pool and hot tub for relaxation after a day out.
₩136,962
₩152,027 total
includes taxes & fees
Oct 8 - Oct 9
Courtyard Marriott Waldorf
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
"I didn’t really like the casino vibe. But I’m sure it was just me."
Christine 1-night trip
Posted 18 hours ago
Rod 'N' Reel Resort
Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

8/10 Good
"Overnight stop during our vacation up north. Hotel was convenient and in a good area for shopping and dining. Young lady at the front desk was pleasant and helpful, but the other staff almost seemed that it was a bother to them when I asked a couple of questions. Overall it was a good hotel and a good overnight stop for us."
Ron 1-night trip
Posted 3 days ago
Holiday Inn Express Waldorf by IHG
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

8/10 Good
"The property was ok. The room was clean and served its purpose. They do offer free breakfast. I would not call what I had breakfast. Cold eggs and a stale muffin. So for the price you it was not worth it."
David 1-night trip
Posted 5 days ago
Springhill Suites by Marriott Prince Frederick
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Breakfast and pool were awesome"
FRANK 3-night trip
Posted 6 days ago
SpringHill Suites by Marriott Annapolis
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

8/10 Good
"No Continental Breakfast ! No 24/7 Coffee Bar ! And Pay for Parking is No Way to greet your customers !!"
Kathy 3-night trip
Posted 7 days ago
Hilton Garden Inn Solomons

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, Rod n Reel Charter Fishing, and Northern Chesapeake Bay. 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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