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
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Chesapeake Beach hotels with a pool

A swimming pool with a 3ft 6in depth, surrounded by lounge chairs and a dining area with tables and chairs.
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.
P11,770
P15,122 total
includes taxes & fees
Aug 26 - Aug 27
Rod 'N' Reel Resort
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.
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."
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.
P7,118
P7,901 total
includes taxes & fees
Aug 24 - Aug 25
Springhill Suites by Marriott Prince Frederick
A large indoor swimming pool with clear blue water, surrounded by windows and chairs.
A buffet with labeled food stations including omelets and cheese.
A hotel room with a large bed, bedside tables, a desk, a chair, a flat-screen TV, and a window with a view.
A hotel with a prominent sign, a covered entrance, and a parking area with a handicapped parking space.

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.
P7,109
P8,578 total
includes taxes & fees
Sep 20 - Sep 21
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 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.
P12,458
P14,202 total
includes taxes & fees
Sep 15 - Sep 16
Anchored Inn at Hidden Harbour Marina
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
A hotel room with two beds, a chair, and a painting on the wall.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

5. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
P5,505
P6,056 total
includes taxes & fees
Aug 31 - Sep 1
St Michaels Inn
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 covered patio area with wicker furniture and a view of a building with large windows.
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.
P9,268
P10,195 total
includes taxes & fees
Aug 26 - Aug 27
Knapps Narrows Marina & Inn
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.
An outdoor bar area with a view of the lake, wooden deck, and metal roof structure.
A large building with a swimming pool, dock, and green surroundings.

7. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
P13,903
P15,293 total
includes taxes & fees
Aug 24 - Aug 25
The Tilghman Island Inn
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 modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

8. 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.
P5,997
P6,836 total
includes taxes & fees
Aug 30 - Aug 31
Sonesta ES Suites Annapolis
A swimming pool with lounge chairs and a door.
A reception area with two wooden reception desks, a green wall with a grass-like design, and a digital screen displaying information.
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 with a fire pit in the courtyard, outdoor seating, and a brick facade.

9. Courtyard Marriott Waldorf

Courtyard Marriott Waldorf
Waldorf
  • Aquatic retreat awaits with indoor pool and hot tub for relaxation after a day out.
P6,202
P6,884 total
includes taxes & fees
Aug 27 - Aug 28
Courtyard Marriott Waldorf
A swimming pool with metal railings, a tiled deck, and a white building with windows.
A hotel lobby with a fireplace, a reception desk, and a seating area.
A covered outdoor seating area with wicker furniture and large windows.
A modern living room with a fireplace, sofas, and a large window.

10. Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
Solomons
  • Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
P8,056
P8,942 total
includes taxes & fees
Aug 28 - Aug 29
Hilton Garden Inn Solomons
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

8/10 Good
"Staff was great, room was clean,breakfast was fresh every day"
Beverly 2-night trip
Posted 18 hours ago
Sonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"We had a really nice stay. Wish it could've been longer and Casino was nice too. A water park or bigger outdoor pool would be nice."
Paula 2-night trip
Posted 18 hours ago
Rod 'N' Reel Resort
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

10/10 Excellent
"The place was large and clean. The rooms are very comfortable. The TVs worked very well. The staff was friendly. The beds were comfortable. The pool was great. The weight room was wonderful and they gave you a large full hot breakfast. One of the best hotels I stayed in for a long time."
Melvin 1-night trip
Posted 2 days ago
Springhill Suites by Marriott Prince Frederick
Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

8/10 Good
"I like the property and location and staff was nice"
Anthony 1-night trip
Posted 3 days ago
Holiday Inn Express Waldorf by IHG
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Amazing experience highly recommend"
Andrew 2-night trip
Posted 4 days ago
Inn at Perry Cabin
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

10/10 Excellent
"Hotel was conveniently located, staff were helpful, and room was comfortable."
Mary 1-night trip
Posted 13 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. Inn at Perry Cabin: Provides a full-service spa, an outdoor pool, and 2 bars. Sonesta ES Suites Annapolis: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. Econo Lodge Andrews Air Force Base: Features a snack bar/deli, an indoor pool, and daily.
What is there to see and do in Chesapeake Beach?
Make a point to visit attractions like Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. During your stay, check out sights such as Rod n Reel Charter Fishing, Bruce Gabrielson's Surf Art Gallery and Museum, and Breezy Point Beach. 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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