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

Find Hotels with a Pool in Chesapeake Beach, MD

Check availability on Chesapeake Beach Hotels with a Pool

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Oct 17 - Oct 18
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Oct 18 - Oct 19
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Oct 23 - Oct 25
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Oct 30 - Nov 1

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 modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
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.
$132 nightly
$146 total
Oct 27 - Oct 28
Total with taxes and fees
Rod 'N' Reel Resort
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 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.

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.
$118 nightly
$131 total
Oct 21 - Oct 22
Total with taxes and fees
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.
$128 nightly
$142 total
Oct 21 - Oct 22
Total with taxes and fees
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 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."

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.
$190 nightly
$217 total
Oct 27 - Oct 28
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
A swimming pool with multiple people swimming and lounging around.
A building with a sign reading "The Inn."
A covered patio area with wicker furniture and a view of a building with large windows.
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.
$150 nightly
$165 total
Oct 18 - Oct 19
Total with taxes and fees
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 large building with a swimming pool, dock, and green surroundings.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

6. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
$185 nightly
$204 total
Oct 19 - Oct 20
Total with taxes and fees
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 waterfront hotel with a covered dock and a large building with multiple balconies.

7. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
$228 nightly
$250 total
Oct 18 - Oct 19
Total with taxes and fees
Wylder Tilghman Island
A pool with two Adirondack chairs and a basket of items on the grass.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

8. 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.
$342 nightly
$390 total
Nov 3 - Nov 4
Total with taxes and fees
The Inn at Tacaro Estate
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 reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

9. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$81 nightly
$89 total
Nov 17 - Nov 18
Total with taxes and fees
St Michaels Inn
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 hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

10. 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.
$94 nightly
$107 total
Nov 11 - Nov 12
Total with taxes and fees
Sonesta ES Suites Annapolis
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Choose what matters most at hotels with a pool in Chesapeake Beach

Breakfast included
Hot tub
Spa
5 stars
4 stars

Top Chesapeake Beach Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"First time staying at the resort. We stayed two nights to celebrate my wife's birthday. I had ordered flowers that were delivered before our arrival and frontbdesk had them delivered to our room. The views from the waterfront tower build were amazing. The entire resort is very clean and well maintained. Good choice of restaurants/bars on site. Other restaurants are walkable or a short drive. The casino was surprisingly quiet and very clean, relaxing way to pass some time and maybe win some money. Enjoyed walking though the railroad museum that is on site as well. Everyone on this property were friendly and helpful. Will definitely return!"
James 2-night trip
Posted 22 hours ago
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 23 hours ago
St Michaels Inn
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Stay was exceptional!!"
Kaiya 1-night trip
Posted 3 days ago
SpringHill Suites by Marriott Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 6 days ago
Sonesta ES Suites Annapolis
Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf

10/10 Excellent
"Clean & comfy room. Nice staff."
Alicia 6-night trip
Posted 9 days ago
Residence Inn by Marriott Waldorf

Frequently asked questions

What are the best hotels in Chesapeake Beach with outdoor pools?
Rod 'N' Reel Resort is a fantastic 4-star option for travellers seeking a delightful stay in Chesapeake Beach, especially those in search of an outdoor pool. With a traveller review score of 8.4, guests rave about the resort's friendly staff and comfortable, clean rooms, creating an inviting space for travellers.The resort features a lovely outdoor pool complemented by cabanas and sun loungers, great for relaxing after a day spent exploring the beautiful surroundings. Visitors can enjoy the scenic views and a refreshing dip, making it an ideal spot for families with children who love to splash around.Additionally, the resort's excellent food options add to its appeal, ensuring that guests can refuel without needing to venture far.
How much does a hotel with outdoor pool in Chesapeake Beach cost?
Enjoy staying in a hotel in Chesapeake Beach with an outdoor pool. You can find a great deal from $89 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
What are some of the best Chesapeake Beach hotels with outdoor pools and scenic views?
Rod 'N' Reel Resort is a delightful 4-star option for families and travellers seeking both relaxation and adventure in Chesapeake Beach. Guests have consistently praised the resort, giving it an impressive review rating of 8.4, highlighting the friendly and excellent staff, comfortable and clean rooms, and beautiful location.This resort features an inviting outdoor pool surrounded by sun loungers and cabanas, great for soaking up the sun while enjoying stunning views of the water and marina. Families appreciate the convenience of having a poolside area where they can unwind after a day of exploring the nearby attractions. Additionally, the resort's on-site dining options boast quality food, ensuring you can enjoy delicious meals without having to venture far from your relaxing retreat.
Are there hotels in Chesapeake Beach with outdoor pool cabanas or loungers?
Rod 'N' Reel Resort is a fantastic 4-star option for travellers seeking a delightful stay in Chesapeake Beach. This hotel boasts an inviting outdoor pool complete with luxurious cabanas and comfortable loungers, great for relaxing while soaking up the sun.Guests appreciate the resort's warm and friendly staff, who go above and beyond to ensure a pleasant experience. With a traveller rating of 8.4, the resort is frequently lauded for its clean and comfortable rooms, excellent food options, and beautiful location.
Are there hotels with outdoor pools that are close to Chesapeake Beach Railway Museum?
Rod 'N' Reel Resort is a charming 4-star hotel that perfectly blends comfort and adventure, making it an excellent choice for families visiting the Chesapeake Beach area. This resort boasts an inviting outdoor pool, complete with sun loungers and pool cabanas, where guests can unwind while enjoying the beautiful Maryland weather. With a traveller rating of 8.4, visitors frequently praise the resort's friendly staff, comfortable rooms, and excellent dining options.Situated close to the Chesapeake Beach Railway Museum, this hotel allows families to explore local history while having a relaxing retreat nearby. The combination of quality amenities and a fantastic location makes Rod 'N' Reel Resort a great option for those seeking both leisure and adventure during their stay.
Is it cheaper to book flights and a Chesapeake Beach hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Chesapeake Beach for you.

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