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

Search Hotels with Swimming Pool in Chesapeake Beach

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Check availability on Chesapeake Beach Hotels with Swimming Pool

Tonight
13 Sept - 14 Sept
Tomorrow
14 Sept - 15 Sept
Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 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 salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
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.
₹12,849
₹14,263 total
includes taxes & fees
14 Oct - 15 Oct
Rod 'N' Reel Resort
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 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 coffee machines and a variety of coffee pods and cups.

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.
₹11,276
₹13,577 total
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express Prince Frederick by IHG
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.
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.
A hotel lobby with multiple seating areas, including tables and chairs, a television mounted on the wall, and a kitchen area in the background.

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.
₹11,290
₹12,532 total
includes taxes & fees
20 Sept - 21 Sept
Springhill Suites by Marriott Prince Frederick
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 black Mercedes-Benz SUV parked in front of a building with a sign that reads "Anchored Inn at Hidden Harbour Marina."
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.

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.
₹19,695
₹22,452 total
includes taxes & fees
14 Sept - 15 Sept
Anchored Inn at Hidden Harbour Marina
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 marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.
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.
₹14,334
₹15,767 total
includes taxes & fees
14 Sept - 15 Sept
Knapps Narrows Marina & Inn
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
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.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

6. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
₹8,308
₹9,139 total
includes taxes & fees
16 Sept - 17 Sept
St Michaels 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.
A spacious indoor dining area with large windows, tables, and chairs.
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.
₹19,590
₹21,548 total
includes taxes & fees
16 Sept - 17 Sept
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 gym with treadmills, weight machines, and dumbbells.

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 centre.
₹9,269
₹10,567 total
includes taxes & fees
20 Sept - 21 Sept
Sonesta ES Suites Annapolis
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 waterfront hotel with a covered dock and a large building with multiple balconies.
A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.

9. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
₹16,126
₹22,516 total
includes taxes & fees
14 Sept - 15 Sept
Wylder Tilghman Island
A pool with two Adirondack chairs and a basket of items on the grass.
A hot tub in a grassy area with a building in the background.
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.

10. 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.
₹36,385
₹41,479 total
includes taxes & fees
14 Oct - 15 Oct
The Inn at Tacaro Estate
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

10/10 Excellent
"Very nice room Not far from St. Michaels. Plenty of parking. Nice breakfast. Thank you."
Darlene 2-night trip
Posted 1 hour ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Check in was easy, friendly staff, and our room was very clean. Comfy bed and super close to everything we wanted to do in Annapolis."
Andrea 2-night trip
Posted 3 hours ago
Sonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"Nice hotel. Resort is a bit of a stretch. Great place to stay for a couple nights. Outdoor concert set up is nice."
Alex 2-night trip
Posted 5 hours ago
Rod 'N' Reel Resort
Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

8/10 Good
"Staff friendly.Our room was clean no issues .Will return if in the area."
Marcus 1-night trip
Posted 2 days ago
Holiday Inn Express Waldorf by IHG
Wingate by Wyndham Waldorf/Washington DC Area

Wingate by Wyndham Waldorf/Washington DC Area

10/10 Excellent
"Everything was perfect! Great price and I have a wonderful experience with my stay! Highly recommend for sure!"
Amari 3-night trip
Posted 2 days ago
Wingate by Wyndham Waldorf/Washington DC Area
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Susan 1-night trip
Posted 5 days ago
Inn at Perry Cabin

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. Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. St Michaels Inn: Provides daily, a seasonal outdoor pool and free self parking. Inn at Perry Cabin: Features a full-service spa, an outdoor pool and 2 bars. Spark by Hilton Waldorf: Features buffet, an indoor pool and free self parking.
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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