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

Hotels with Swimming Pools in Chesapeake Beach

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Beach Hotels with Swimming Pools

Our top choices for Chesapeake Beach hotels with a pool

Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is S$285
includes taxes & fees
9 Aug - 10 Aug
Rod 'N' Reel Resort
Indoor pool

Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG
2.5 star property
Prince Frederick
8.8 out of 10, Excellent, (739 reviews)
  • cleanliness
    Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.
The price is S$152
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Prince Frederick by IHG
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,004 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is S$134
includes taxes & fees
28 Jul - 29 Jul
St Michaels Inn
Indoor pool

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick
3.0 star property
Prince Frederick
8.6 out of 10, Excellent, (973 reviews)
  • cleanliness
    Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.
The price is S$165
includes taxes & fees
23 Jul - 24 Jul
Springhill Suites by Marriott Prince Frederick
Outdoor pool

Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
3.0 star property
Solomons
8.6 out of 10, Excellent, (687 reviews)
  • cleanliness
    Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
The price is S$187
includes taxes & fees
14 Aug - 15 Aug
Hilton Garden Inn Solomons
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (389 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is S$213
includes taxes & fees
22 Jul - 23 Jul
Knapps Narrows Marina & Inn
Outdoor pool

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (492 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is S$344
includes taxes & fees
2 Aug - 3 Aug
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool, pool umbrellas

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (144 reviews)
  • cleanliness
    Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
The price is S$319
includes taxes & fees
9 Aug - 10 Aug
The Tilghman Island Inn
Indoor pool

Courtyard Marriott Waldorf

Courtyard Marriott Waldorf
3.0 star property
Waldorf
8.2 out of 10, Very good, (985 reviews)
  • cleanliness
    Aquatic retreat awaits with indoor pool and hot tub for relaxation after a day out.
The price is S$150
includes taxes & fees
2 Aug - 3 Aug
Courtyard Marriott Waldorf
Seasonal outdoor pool

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.
The price is S$162
includes taxes & fees
2 Aug - 3 Aug
Sonesta ES Suites Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Chesapeake Beach

Breakfast included
Hot tub

Top Chesapeake Beach Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Todo exelente"
Adela 1-night trip
Posted 1 hour ago
St Michaels Inn

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. Econo Lodge Andrews Air Force Base: Offers a full-service spa, an outdoor pool and 2 bars. Spark by Hilton Waldorf: Features buffet, a seasonal outdoor pool and complimentary wireless Internet access. Inn at Perry Cabin: Offers a snack bar/deli, an indoor pool and daily.
What is there to see and do in Chesapeake Beach?
Make a point to visit attractions such as Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. During your stay, visit sights such as Rod n Reel Charter Fishing, Breezy Point Beach and Northern Chesapeake Bay. 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.

Explore a world of travel with Expedia