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

Search Hotels with Pool in Chesapeake Beach

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Check availability on Chesapeake Beach Hotels with Pool

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

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 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.
฿3,226
฿4,669 total
includes taxes & fees
3 Sept - 4 Sept
Rod 'N' Reel Resort
A hotel room with a large bed, bedside tables, a desk, a chair, a flat-screen TV, and a window with a view.
A swimming pool with clear blue water, surrounded by sunlit arched windows and a row of chairs.
A Holiday Inn Express hotel with a central entrance, two flagpoles, and a well-lit facade.
A spacious living area with a fireplace, a television, and a seating area with two chairs.

2. 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.
฿3,596
฿4,354 total
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Express Prince Frederick by IHG
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.
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.
A hotel lobby with a reception desk, a glass-top table with a bowl, potted plants, a vending machine, and a large window.

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.
฿3,862
฿4,287 total
includes taxes & fees
30 Aug - 31 Aug
Springhill Suites by Marriott Prince Frederick
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 restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

4. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
฿2,922
฿3,215 total
includes taxes & fees
31 Aug - 1 Sept
St Michaels Inn
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 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.
฿4,903
฿5,394 total
includes taxes & fees
30 Aug - 31 Aug
Knapps Narrows Marina & Inn
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.

6. 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.
฿6,512
฿7,424 total
includes taxes & fees
8 Sept - 9 Sept
Anchored Inn at Hidden Harbour Marina
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.

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 centre.
฿3,214
฿3,664 total
includes taxes & fees
23 Sept - 24 Sept
Sonesta ES Suites Annapolis
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
An outdoor bar area with a view of the lake, wooden deck, and metal roof structure.
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.

8. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
฿6,701
฿7,371 total
includes taxes & fees
16 Sept - 17 Sept
The Tilghman Island Inn
A swimming pool with metal railings, a tiled deck, and a white building with windows.
A hotel reception area with a self-service beverage station, snack vending machines, and a minibar.
A modern living room with a fireplace, sofas, and a large window.
A hotel lobby with a fireplace, a reception desk, and a seating area.

9. Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
Solomons
  • Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
฿4,262
฿4,731 total
includes taxes & fees
2 Sept - 3 Sept
Hilton Garden Inn Solomons
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 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.

10. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
฿7,252
฿9,611 total
includes taxes & fees
1 Sept - 2 Sept
Wylder Tilghman Island
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

8/10 Good
"My room was wonderful! Great comfort of the bed. Peaceful. The breakfast was lack luster with all carbs. Nothing sugar free for diabetics. Lots of construction and painting during my stay. Would stay here again, however!"
Kris 3-night trip
Posted 6 hours ago
St Michaels Inn
Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

10/10 Excellent
"Front desk staff were very friendly, and helpful, and I was greeted upon coming downstairs, or coming in the front door. Breakfast both mornings of my stay was excellent, with offerings I don’t usually see at most hotels. Entire hotel was clean, fresh, and up to date looking. Will definitely stay here again when I am in the area!"
Heather 2-night trip
Posted 7 hours ago
Holiday Inn Express Prince Frederick by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Spacious rooms, very good breakfast selection, even had tacos for breakfast!"
Sophia 1-night trip
Posted 11 hours ago
Sonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The staff went out of their way for me and I complimented them on how well they took care of the property"
James 1-night trip
Posted 15 hours ago
Rod 'N' Reel Resort
Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

10/10 Excellent
"The best part was the pool for me!!! Have Sciatic Nerve Damage I've been wanting to do some Aquatics! I finally got a chance to a great start! Water was COLD 略 but I adjusted! If the water was heated it would've been GRAND❤️❤️❤️I'll be still sitting in there till this day藍藍藍Thank you so much for your wonderful hospitality! I will be back!! ⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐"
Shontikki 1-night trip
Posted 2 days ago
Holiday Inn Express Waldorf by IHG
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

10/10 Excellent
"I loved the hotel however, the bathroom shower curtain bar was leaning forward and needs to be adjusted. Water from the shower kept getting all over the floor and we had to use the towels to soak up the floor water. So I called and they never brought new ones. I went to the front desk and they never brought new ones. On my way out I mentioned it and got points on my Marriott account. Did not do me any good. Thank goodness we had access to the pool towels. I gave a low rating on maintenance because the wallpaper seams in the bathrooms are starting to separate and look cruddy. The bed was comfortable and the food was decent. Staff are friendly except the guy who swore because I asked him where the ice machine was. All else good."
judith 2-night trip
Posted 2 days ago
Springhill Suites by Marriott Prince Frederick

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?
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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