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Hotels with Pool & Resorts in Chesapeake Beach from AU$156

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Check availability on Chesapeake Beach Hotels with Pool

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

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is AU$175
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
Indoor pool
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick
3.0 star property
Prince Frederick
8.6 out of 10, Excellent, (937)
"Everything was perfect, from the room and staff and the breakfast"
United States
Louise
The price is AU$163
includes taxes & fees
20 Dec - 21 Dec
Springhill Suites by Marriott Prince Frederick
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is AU$288
includes taxes & fees
12 Jan - 13 Jan 2026
Wylder Tilghman Island
Indoor pool
Holiday Inn Express Prince Frederick by IHG

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, (693)
"Great environment, friendly staff, great place to stay with family and lots of things to do around the area!"
United States
Rosemary
The price is AU$189
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Prince Frederick by IHG
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (361)
"nice clean room staff very nice would stay again "
United States
mario
The price is AU$199
includes taxes & fees
19 Dec - 20 Dec
Knapps Narrows Marina & Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1000)
"Staff was friendly, courteous, and helpful."
United States
Donna
The price is AU$179
includes taxes & fees
18 Dec - 19 Dec
St Michaels Inn
Outdoor pool
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
3.0 star property
Solomons
8.6 out of 10, Excellent, (640)
"Was a great and pleasant experience "
United States
MARLON
The price is AU$192
includes taxes & fees
23 Dec - 24 Dec
Hilton Garden Inn Solomons
Exterior
George Brooks House B&B

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is AU$254
includes taxes & fees
1 Jan - 2 Jan 2026
George Brooks House B&B
Outdoor pool
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is AU$230
includes taxes & fees
28 Dec - 29 Dec
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (964)
"Clean, spacious, quiet, convenient location. I’d stay there again. "
United States
Michael
The price is AU$156
includes taxes & fees
5 Jan - 6 Jan 2026
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.
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Top Chesapeake Beach Hotel Reviews

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

10/10 Excellent
"The staff at the breakfast bar was very attentive, and detail oriented. She was very good about checking everything. She very friendly and helpful. "
Dave 1-night trip
Posted 3 days ago
Springhill Suites by Marriott Prince Frederick

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. Spark by Hilton Waldorf: Provides a snack bar/deli, a seasonal outdoor pool and full. Residence Inn by Marriott Waldorf: Features buffet, a seasonal outdoor pool and complimentary wireless Internet access. Sonesta ES Suites Annapolis: Features a snack bar/deli, an indoor pool and daily. Candlewood Suites Annapolis by IHG: Features a full-service spa, an outdoor pool and 2 bars.
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.