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

Find Hotels with a Pool in Chesapeake Beach, MD

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Check availability on Chesapeake Beach Hotels with a Pool

Tonight
11 Aug - 12 Aug
Tomorrow
12 Aug - 13 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Chesapeake Beach hotels with a pool

Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
Interior
Coffee shop
Outdoor wedding area

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.
AED 679
AED 876 total
includes taxes & fees
19 Aug - 20 Aug
Rod 'N' Reel Resort
Indoor pool
Standard Room, 1 King Bed | In-room safe, iron/ironing board, cribs (free)
Exterior
Exterior

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.
AED 404
AED 489 total
includes taxes & fees
10 Sep - 11 Sep
Holiday Inn Express Prince Frederick by IHG
Indoor pool
Reception
Lobby
Free daily buffet breakfast

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.
AED 408
AED 453 total
includes taxes & fees
16 Aug - 17 Aug
Springhill Suites by Marriott Prince Frederick
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Reception
Standard Double Room, 2 Double Beds | Desk, blackout drapes, iron/ironing board, WiFi (free)
Banquet hall

4. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
AED 314
AED 346 total
includes taxes & fees
31 Aug - 1 Sep
St Michaels Inn
Seasonal outdoor pool
Exterior
First Floor Bay View Queen Room with Patio | View from room
Terrace/patio

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
AED 551
AED 606 total
includes taxes & fees
18 Aug - 19 Aug
Knapps Narrows Marina & Inn
Outdoor pool
Bar (on property)
Property entrance
View from property

6. 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.
AED 740
AED 844 total
includes taxes & fees
7 Sep - 8 Sep
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool, pool umbrellas
Free daily on-the-go breakfast
Front of property
Meeting facility

7. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
AED 826
AED 909 total
includes taxes & fees
12 Aug - 13 Aug
The Tilghman Island Inn
Seasonal outdoor pool
Egyptian cotton sheets, premium bedding, pillowtop beds, desk
Terrace/patio
Free daily buffet breakfast

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 center.
AED 364
AED 415 total
includes taxes & fees
2 Sep - 3 Sep
Sonesta ES Suites Annapolis
Indoor pool
Free daily buffet breakfast
Standard Room, 1 King Bed with Sofa bed | In-room safe, desk, blackout drapes, iron/ironing board
Exterior

9. Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG
Waldorf
  • Dive into poolside relaxation at this colonial-style hotel, where free cabanas add luxury to the indoor swimming experience.
AED 342
AED 379 total
includes taxes & fees
8 Sep - 9 Sep
Holiday Inn Express Waldorf by IHG
Indoor pool, sun loungers
Point of interest
Pillowtop beds, in-room safe, desk, laptop workspace
Reception

10. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
  • Splash into serenity with a revitalizing indoor pool escape at this newly remodeled Annapolis hotel.
AED 437
AED 498 total
includes taxes & fees
30 Aug - 31 Aug
SpringHill Suites by Marriott Annapolis
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Loved my stay!"
Joshua 2-night trip
Posted 6 hours ago
SpringHill Suites by Marriott Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"Service"
Arnold 2-night trip
Posted 15 hours ago
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

10/10 Excellent
"We enjoyed our stay. Rooms were clean and the staff were very friendly. Looking forward to our next visit to St Michael’s. We would definitely stay here again."
Lori 2-night trip
Posted 23 hours ago
St Michaels Inn
Courtyard Marriott Waldorf

Courtyard Marriott Waldorf

10/10 Excellent
"Great time. Would definitely return"
Kennon 2-night trip
Posted 8 days ago
Courtyard Marriott Waldorf

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: Features a full-service spa, an outdoor pool, and 2 bars. Inn at Perry Cabin: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Sonesta ES Suites Annapolis: Features 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 like Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. During your stay, check out 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 an accommodation with an outdoor swimming pool if you plan to visit Chesapeake Beach in the hottest months of July, August, or June when the average temperature is 75°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temperature is 40°F.