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
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Chesapeake Beach hotels with a pool

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.
NT$4,575
NT$6,132 total
includes taxes & fees
Oct 7 - Oct 8
Rod 'N' Reel Resort

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.
NT$3,734
NT$4,496 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Express Prince Frederick by IHG

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.
NT$3,739
NT$4,150 total
includes taxes & fees
Sep 20 - Sep 21
Springhill Suites by Marriott Prince Frederick

4. 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.
NT$6,522
NT$7,435 total
includes taxes & fees
Sep 14 - Sep 15
Anchored Inn at Hidden Harbour Marina

5. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
NT$4,747
NT$5,221 total
includes taxes & fees
Sep 14 - Sep 15
Knapps Narrows Marina & Inn

6. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
NT$2,990
NT$3,289 total
includes taxes & fees
Sep 14 - Sep 15
St Michaels Inn

7. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
NT$6,487
NT$7,136 total
includes taxes & fees
Sep 16 - Sep 17
The Tilghman Island Inn

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.
NT$3,069
NT$3,499 total
includes taxes & fees
Sep 20 - Sep 21
Sonesta ES Suites Annapolis

9. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
NT$6,052
NT$8,239 total
includes taxes & fees
Sep 14 - Sep 15
Wylder Tilghman Island

10. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
  • Escape to a seasonal outdoor paradise with a hot tub and 24-hour pool access at this luxury bed & breakfast.
NT$12,551
NT$14,308 total
includes taxes & fees
Sep 14 - Sep 15
The Inn at Tacaro Estate
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

St Michaels Inn

St Michaels Inn

8/10 Good
"Well, it was a nice hotel and the price was reasonable, but it’s a little rundown the rooms inside a very nice, but the overall property is certainly not pretty. The other thing is it’s kind of a mix between nice and not so nice. Breakfast was less than average coffee was weak and not that good but again if you want to stay near Saint Michael’s and don’t have to travel in from Easton it’s a it’s an OK pick"
Jeffrey 1-night trip
Posted 12 hours ago
St Michaels Inn
Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

8/10 Good
"Staff friendly.Our room was clean no issues .Will return if in the area."
Marcus 1-night trip
Posted 2 days ago
Holiday Inn Express Waldorf by IHG
Wingate by Wyndham Waldorf/Washington DC Area

Wingate by Wyndham Waldorf/Washington DC Area

10/10 Excellent
"Everything was perfect! Great price and I have a wonderful experience with my stay! Highly recommend for sure!"
Amari 3-night trip
Posted 2 days ago
Wingate by Wyndham Waldorf/Washington DC Area
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"great place good price"
Adam 4-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

8/10 Good
"for a suite, it would be much better to have a few more towel hangers in the bathroom. It helps towel reuses."
Suibin 4-night trip
Posted 4 days ago
SpringHill Suites by Marriott Annapolis
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Susan 1-night trip
Posted 5 days ago
Inn at Perry Cabin

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. Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. St Michaels Inn: Provides daily, a seasonal outdoor pool, and free self parking. Inn at Perry Cabin: Features a full-service spa, an outdoor pool, and 2 bars. Spark by Hilton Waldorf: Features buffet, an indoor pool, and free self parking.
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, check out 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 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.

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