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

Search Hotels with Swimming Pool 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 Pool

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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.

1. 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 ₹12,653
₹17,212 total
includes taxes & fees
9 Nov - 10 Nov
Rod 'N' Reel Resort
A swimming pool with clear blue water, surrounded by sunlit arched windows and a row of chairs.

2. 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, (776 reviews)
  • cleanliness
    Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.
The price is ₹11,224
₹13,514 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express Prince Frederick by IHG
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.

3. Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick
3.0 star property
Prince Frederick
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.
The price is ₹11,238
₹12,475 total
includes taxes & fees
9 Nov - 10 Nov
Springhill Suites by Marriott Prince Frederick
A swimming pool with blue lounge chairs and a building with balconies in the background.

4. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (521 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is ₹15,350
₹17,499 total
includes taxes & fees
29 Nov - 30 Nov
Anchored Inn at Hidden Harbour Marina
A swimming pool with multiple people swimming and lounging around.

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (401 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is ₹12,365
₹13,602 total
includes taxes & fees
1 Nov - 2 Nov
Knapps Narrows Marina & Inn
A pool with two Adirondack chairs and a basket of items on the grass.

6. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (20 reviews)
  • cleanliness
    Escape to a seasonal outdoor paradise with a hot tub and 24-hour pool access at this luxury bed & breakfast.
The price is ₹33,275
₹37,934 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Tacaro Estate
A swimming pool with a wooden deck, lounge chairs, and a fenced area.

7. The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (172 reviews)
  • cleanliness
    Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
The price is ₹26,188
₹28,807 total
includes taxes & fees
30 Oct - 31 Oct
The Tilghman Island Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

8. Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
9.0 out of 10, Wonderful, (122 reviews)
  • cleanliness
    Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
The price is ₹22,343
₹29,334 total
includes taxes & fees
1 Nov - 2 Nov
Wylder Tilghman Island
A swimming pool with lounge chairs and a fence.

9. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.
The price is ₹8,190
₹9,336 total
includes taxes & fees
29 Nov - 30 Nov
Sonesta ES Suites Annapolis
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

10. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (407 reviews)
  • cleanliness
    Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
The price is ₹46,141
₹50,755 total
includes taxes & fees
11 Nov - 12 Nov
Inn at Perry Cabin
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

8/10 Good
"Breakfasr was in lobby consisting of package roles and coffee. No toaster, no microwave, no cereal or eggs or bacon or yougert. Room and parking and staff werefine."
John 1-night trip
Posted 14 hours 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. Sonesta ES Suites Annapolis: Provides buffet, a seasonal outdoor pool and complimentary wireless Internet access. Holiday Inn Express Waldorf by IHG: Features buffet, an indoor pool and free self parking. SpringHill Suites by Marriott Annapolis: Offers a snack bar/deli, an indoor pool and daily.
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.