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

Chesapeake Beach Hotel Guide - Hotels with Pool in Chesapeake Beach, Maryland

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Check availability on Chesapeake Beach Hotels with Pool

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

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 staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

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.
€210
includes taxes & fees
7 Sept - 8 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.
€114
includes taxes & fees
31 Aug - 1 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 lobby with multiple seating areas, including tables and chairs, a television mounted on the wall, and a kitchen area in the background.
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.
€113
includes taxes & fees
6 Sept - 7 Sept
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 reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

4. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
€84
includes taxes & fees
31 Aug - 1 Sept
St Michaels Inn
A swimming pool with multiple people swimming and lounging around.
A waterfront property with houses, a dock, and a grassy area.
A building with a sign reading "The Inn."
A covered patio area with wicker furniture and a view of a building with large windows.

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
€142
includes taxes & fees
29 Aug - 30 Aug
Knapps Narrows Marina & Inn
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 black Mercedes-Benz SUV parked in front of a building with a sign that reads "Anchored Inn at Hidden Harbour Marina."

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.
€195
includes taxes & fees
8 Sept - 9 Sept
Anchored Inn at Hidden Harbour Marina
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 gym with treadmills, weight machines, and dumbbells.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

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.
€96
includes taxes & fees
22 Sept - 23 Sept
Sonesta ES Suites Annapolis
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 large building with a swimming pool, dock, and green surroundings.
An outdoor bar area with a view of the lake, wooden deck, and metal roof structure.

8. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
€194
includes taxes & fees
30 Aug - 31 Aug
The Tilghman Island Inn
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.

9. Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
Solomons
  • Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
€124
includes taxes & fees
3 Sept - 4 Sept
Hilton Garden Inn Solomons
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 view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.

10. Wylder Tilghman Island

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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"It look like they did a lot of upgrades very nice. I really appreciate the staff and service. I will be back soon 😉"
Frankie 1-night trip
Posted 10 hours ago
Rod 'N' Reel Resort
Towneplace Suites by Marriott Clinton at Joint Base Andrews

Towneplace Suites by Marriott Clinton at Joint Base Andrews

10/10 Excellent
"The room was clean, staff were nice, and there was a good variety of food for breakfast."
Jailene 1-night trip
Posted 19 hours ago
Towneplace Suites by Marriott Clinton at Joint Base Andrews
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

8/10 Good
"The property, including the room, was clean. The staff was friendly and attentive. Breakfast was okay (continental) and staff will accommodate if needed for dietary restrictions. The dining area is small but does have tables with seats/high chairs to sit. There are two computers, a laundry room, ice room, and an exercise room. Based on a window peep, there is a disabled accessible pool/jaccuzi, but it was closed for maintenance during our stay and reopened on our check-out day so we didn't get to use it. One of the issues we experienced was getting a parking citation everyday even though we paid at check-in. The desk clerk assured we wouldn't be towed and the company would be notified by email regarding the error, but it still was frustrating. Parking is $9.50/day via third party scan code or text to pay through a website. The second issue was our microwave did not work properly but we used the common one downstairs. The final issue was our mini-fridge was loud if not closed a certain way yet, it did work to keep our items cold. The location is quiet and felt safe. You have to use your key card to enter the lobby after 12am. Overall, we would choose to book this hotel again if available in the future."
Casey 3-night trip
Posted 22 hours ago
SpringHill Suites by Marriott Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"-"
Chase 1-night trip
Posted 23 hours ago
St Michaels Inn
Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

8/10 Good
"Room was not vaccumed well found candy wrappers and other random small pieces of trash other than that it was perfect for what we needed"
Carlos 1-night trip
Posted 1 day 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 2 days ago
Sonesta ES Suites Annapolis
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 4 days ago
Springhill Suites by Marriott Prince Frederick
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

10/10 Excellent
"Great location with access to all the areas amenities."
William 1-night trip
Posted 4 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?
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.