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

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
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
Nov 10 - Nov 11
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 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.

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.
$114 nightly
$126 total
Oct 27 - Oct 28
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 hotel room with a large bed, bedside tables, a desk, a chair, a flat-screen TV, and a window with a view.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.
A breakfast bar with a yogurt machine, cereal, and hot food options.

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 27 - Oct 28
Total with taxes and fees
Holiday Inn Express Prince Frederick by IHG
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.

4. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
$130 nightly
$143 total
Oct 30 - Oct 31
Total with taxes and fees
Knapps Narrows Marina & Inn
A swimming pool with blue lounge chairs and a building with balconies in the background.
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.
A marina with docked boats, a picnic area, and a grassy lawn with a tree.

5. 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.
$218 nightly
$248 total
Nov 23 - Nov 24
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
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 spacious indoor dining area with large windows, tables, and chairs.
A modern lounge area with a fireplace, seating, and a view of the outdoors.

6. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
$175 nightly
$193 total
Oct 25 - Oct 26
Total with taxes and fees
The Tilghman Island Inn
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 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.
$250 nightly
$275 total
Oct 25 - Oct 26
Total with taxes and fees
Wylder Tilghman Island
A pool with two Adirondack chairs and a basket of items on the grass.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A hot tub in a grassy area with a building in the background.

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.
$381 nightly
$434 total
Nov 23 - Nov 24
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.
$80 nightly
$88 total
Nov 22 - Nov 23
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 patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A gym with treadmills, weight machines, and dumbbells.

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.
$83 nightly
$95 total
Nov 12 - Nov 13
Total with taxes and fees
Sonesta ES Suites Annapolis
View all properties

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

8/10 Good
"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."
William 1-night trip
Posted 20 hours ago
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

8/10 Good
"older facility but kept clean. a good value for an over night"
John 1-night trip
Posted 22 hours ago
St Michaels Inn
Towneplace Suites by Marriott Clinton at Joint Base Andrews

Towneplace Suites by Marriott Clinton at Joint Base Andrews

10/10 Excellent
"Clean comfy and in a great location"
Felicea 2-night trip
Posted 1 day ago
Towneplace Suites by Marriott Clinton at Joint Base Andrews
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Very pleasant surprise! Great price for studio apartment- way better than the Marriott I just checked out of!"
Rhonda 1-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf

10/10 Excellent
"They are remodeling so it's a work in progress. My room was huge and ver comfortable. No complains."
Israel 1-night trip
Posted 4 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 $88 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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