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

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Chesapeake Beach hotels with a pool

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

1. Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is ₹16,579
₹21,588 total
includes taxes & fees
10 Aug - 11 Aug
Rod 'N' Reel Resort
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

2. 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 ₹7,840
₹8,624 total
includes taxes & fees
30 Aug - 31 Aug
St Michaels Inn
Outdoor pool

3. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (395 reviews)
  • cleanliness
    Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
The price is ₹57,699
₹63,468 total
includes taxes & fees
2 Aug - 3 Aug
Inn at Perry Cabin
Exterior

4. George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (76 reviews)
  • cleanliness
    Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
The price is ₹20,229
₹22,252 total
includes taxes & fees
3 Aug - 4 Aug
George Brooks House B&B
Seasonal outdoor pool

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (393 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is ₹14,347
₹15,782 total
includes taxes & fees
4 Aug - 5 Aug
Knapps Narrows Marina & Inn
Seasonal outdoor pool

6. Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
9.0 out of 10, Wonderful, (104 reviews)
  • cleanliness
    Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
The price is ₹28,682
₹36,333 total
includes taxes & fees
31 Jul - 1 Aug
Wylder Tilghman Island
Seasonal outdoor pool, pool umbrellas

7. The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (153 reviews)
  • cleanliness
    Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
The price is ₹21,520
₹23,672 total
includes taxes & fees
9 Aug - 10 Aug
The Tilghman Island Inn
Outdoor pool

8. Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
3.0 star property
Solomons
8.6 out of 10, Excellent, (693 reviews)
  • cleanliness
    Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
The price is ₹13,111
₹14,553 total
includes taxes & fees
9 Aug - 10 Aug
Hilton Garden Inn Solomons
Indoor pool

9. 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, (743 reviews)
  • cleanliness
    Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.
The price is ₹9,909
₹10,999 total
includes taxes & fees
16 Aug - 17 Aug
Holiday Inn Express Prince Frederick by IHG
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.
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Choose what matters most at hotels with a pool in Chesapeake Beach

Breakfast included
Hot tub

Top Chesapeake Beach Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

8/10 Good
"We stayed for 3 days very nice hotel we love the 2 bedrooms suite with separate bedrooms definitely will stay again the only issue is the parking we came back after 10pm from dinner no parking had to park at the building next door but overall the place was very nice!"
Wydia 3-night trip
Posted 14 hours ago
Sonesta ES Suites Annapolis

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 a snack bar/deli, an indoor pool and daily. Inn at Perry Cabin: Features a snack bar/deli, an outdoor pool and complimentary high-speed (wired) Internet access.
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, Bruce Gabrielson's Surf Art Gallery and Museum and Breezy Point Beach. 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.