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Chesapeake Beach Hotel Guide - Hotels with Pool in Chesapeake Beach, Maryland

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Check availability on Chesapeake Beach Hotels with Pool

Tonight
29 Nov - 30 Nov
Tomorrow
30 Nov - 1 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Chesapeake Beach Hotels with Pool

Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
  • Indoor pool
  • Pool loungers
  • Near the beach
8.4 out of 10, Very good, (1002)
Sparkling waters beckon at dual pools, where cabanas offer shaded luxury beside the marina. Beyond refreshing dips, guests enjoy complimentary bicycles, kayaking adventures, and nearby beach access, creating a complete coastal escape.
The price is €117
includes taxes & fees
7 Dec - 8 Dec
Rod 'N' Reel Resort
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (358)
Marina-side seasonal pool creates a serene retreat overlooking Chesapeake Bay waters. Guests appreciate the immaculate rooms with private balconies, complimentary bicycles for island adventures, and boat tours launching steps away.
The price is €95
includes taxes & fees
30 Nov - 1 Dec
Knapps Narrows Marina & Inn
Indoor pool
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

3.0 star property
Prince Frederick
  • Indoor pool
  • Hot tub
8.6 out of 10, Excellent, (928)
Sparkling clean waters welcome swimmers from dawn till 11 PM in the pristine indoor pool. Fitness enthusiasts appreciate the well-maintained exercise centre while the complimentary breakfast buffet energises guests for days filled with aquatic relaxation.
The price is €93
includes taxes & fees
19 Dec - 20 Dec
Springhill Suites by Marriott Prince Frederick
Indoor pool
Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

2.5 star property
Prince Frederick
  • Indoor pool
  • Near the beach
8.8 out of 10, Excellent, (687)
Swimming enthusiasts savour the warm, inviting indoor pool, accessible from early morning until evening. Located near Calvert Cliffs State Park and Running Hare Vineyard, this spotless hotel earns consistent praise for its helpful staff and delicious breakfast variety.
The price is €99
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express Prince Frederick by IHG
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
  • On private beach
8.8 out of 10, Excellent, (89)
Seasonal outdoor swimming beckons travellers from March through October at this waterfront haven. Complementing the pool, a private beach, sauna, and free bicycles create perfect relaxation opportunities along the river's edge.
The price is €153
includes taxes & fees
2 Dec - 3 Dec
Wylder Tilghman Island
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
  • Pool loungers
8.2 out of 10, Very good, (1004)
Sparkling waters beckon at the seasonal outdoor pool, complete with sun loungers and umbrellas from May through September. Conveniently situated near Chesapeake Bay Maritime Museum, this hotel offers continental breakfast and garden views after invigorating local hikes.
The price is €105
includes taxes & fees
1 Dec - 2 Dec
St Michaels Inn
Outdoor pool
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

3.0 star property
Solomons
  • Outdoor pool
8.6 out of 10, Excellent, (637)
Swimming sessions in the pristine outdoor pool create refreshing breaks from exploring the suburbs. Beyond aquatic delights, Garden Grille and Bar serves American cuisine while a welcoming fireplace in the lobby adds warmth to this exceptionally clean, staff-friendly retreat.
The price is €110
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Solomons
Outdoor pool
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

2.5 star property
Deale
  • Outdoor pool
9.4 out of 10, Exceptional, (470)
Seasonal outdoor pool creates a refreshing oasis surrounded by water views, complemented by peaceful balconies overlooking the marina. Barbecue areas and picnic spots enhance relaxation at this waterfront haven with local seafood nearby.
The price is €132
includes taxes & fees
29 Dec - 30 Dec
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3.0 star property
Edgewater
  • Pool
  • Breakfast included
  • Pet-friendly
  • Free WiFi
  • Air conditioning
  • Gym
8.8 out of 10, Excellent, (956)
Splashes of joy await at the seasonal outdoor pool, complemented by basketball and volleyball courts for active afternoons. This all-suite hotel balances recreation with comfort, featuring cosy fireplaces and fully equipped kitchens in spacious rooms.
The price is €82
includes taxes & fees
21 Dec - 22 Dec
Sonesta ES Suites Annapolis
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings
  • Outdoor pool
  • Near the beach
10.0 out of 10, Exceptional, (48)
The price is €220
includes taxes & fees
30 Nov - 1 Dec
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
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

Top Chesapeake Beach Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"roomy and spacious"
DENNIS RYAN 1-night trip
Posted 3 days ago
Sonesta ES Suites Annapolis

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Frequently asked questions

What are some hotels with pools in Chesapeake Beach?
Rod 'N' Reel Resort: 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. Spark by Hilton Waldorf: Features daily, a seasonal outdoor pool and free self parking. St Michaels Inn: Features a snack bar/deli, a seasonal outdoor pool and full. Candlewood Suites Annapolis by IHG: Provides 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, 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.