The Best Hotels with a Pool in Chesapeake Beach, MD from ₩104,897 in 2026

Q: 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.

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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

Chesapeake Beach

Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.

₩259,027 total

includes taxes & fees

Nov 30 - Dec 1

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

Prince Frederick

Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.

₩189,471 total

includes taxes & fees

Nov 22 - Nov 23

A rectangular swimming pool with a tiled edge, surrounded by blue lounge chairs and white tables.

3. Anchored Inn at Hidden Harbour Marina

Deale

Pool paradise meets scenic marina views for a refreshing escape on the water.

₩245,049 total

includes taxes & fees

Nov 29 - Nov 30

An indoor swimming pool with clear water, tiled walls, and a seating area with tables and chairs.

4. Springhill Suites by Marriott Prince Frederick

Prince Frederick

Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.

₩174,890 total

includes taxes & fees

Nov 18 - Nov 19

A swimming pool with multiple people swimming and lounging around.

5. Knapps Narrows Marina & Inn

Sherwood

Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.

₩176,029 total

includes taxes & fees

Nov 15 - Nov 16

A pool with two Adirondack chairs and a basket of items on the grass.

6. 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.

₩531,828 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

7. Inn at Perry Cabin

Downtown St. Michaels

Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.

₩674,960 total

includes taxes & fees

Dec 7 - Dec 8

A rectangular swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a view of the sea.

8. Wylder Tilghman Island

Tilghman

Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.

₩343,923 total

includes taxes & fees

Dec 1 - Dec 2

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

9. St Michaels Inn

St. Michaels

Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.

₩115,386 total

includes taxes & fees

Nov 17 - Nov 18

A swimming pool with lounge chairs and a fence.

10. Sonesta ES Suites Annapolis

Edgewater

Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness center.

₩121,620 total

includes taxes & fees

Nov 24 - Nov 25

View all properties

Choose what matters most at hotels with a pool in Chesapeake Beach

Breakfast included

Hot tub

Top Chesapeake Beach Hotel Reviews

Rod 'N' Reel Resort

Chesapeake Beach

10/10 Excellent

Huge resort in a small, well kept town! Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable. There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other things)... We were in a hurry to get home so did not try any of the breakfast places that the desk clerk recommended. The staff guy that checked us in was SUPER nice and helpful!

Kathie

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

Holiday Inn Express Prince Frederick by IHG

Prince Frederick

10/10 Excellent

Troy

The Inn at Tacaro Estate

Tracys Landing

10/10 Excellent

ian

Springhill Suites by Marriott Prince Frederick

Prince Frederick

10/10 Excellent

laura

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

An indoor swimming pool with a 3 FT depth marking, surrounded by a tiled floor and a seating area with chairs and a table.

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Julie

Wylder Tilghman Island

Tilghman

10/10 Excellent

We had a great time at the Wylder Inn on Tilghman Island (20-21 May). This is a great spot for a quick getaway, and there are many things to do on site and in the area if you want to stay longer. The staff was welcoming and responsive from our arrival to departure when our key was collected from our car so we didn't have to get out in the rain. The Continental Breakfast had a variety of items to start the day right and the fire pits provided a relaxing venue at the end of the day. We look...

Alan

Sonesta ES Suites Annapolis

Edgewater

10/10 Excellent

This was my first time at this brand of hotel so I didn’t have any expectations. I was surprised in a good way. The room was well appointed for a short stay and very clean. The kitchen was fully stocked. The gym was small but had everything I needed for a couple of workouts. There was also a very well stocked breakfast in the morning. I have special food needs and I found plenty to eat. The entire staff was pleasant and helpful. I had never been there before but will definitely go back.

Sheree

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

D

A swimming pool with metal railings, a tiled deck, and a white building with windows.

Hilton Garden Inn Solomons

Solomons

10/10 Excellent

Anonymous traveler

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

George Brooks House B&B

St. Michaels

10/10 Excellent

Excellent B&B with a pool! the pool was clutch because we were there probably on the hottest days of the year so going in after a long day of walking around was nice. Used the pool until 10pm. Food was good, room was clean, people were nice. What else could you ask for. The only thing I noticed (and it wasn't a big deal) was the mirror in the room was too low on the wall (I'm 5'8 and still had to bend a little) and there was only one mirror so if you're in a hurry getting ready with your spouse...

Anonymous traveler

A swimming pool with clear water, surrounded by windows and chairs.

Towneplace Suites by Marriott Clinton at Joint Base Andrews

Clinton

10/10 Excellent

donna

St Michaels Inn

St. Michaels

10/10 Excellent

Lori

A swimming pool with lounge chairs and a door.

Courtyard Marriott Waldorf

Waldorf

10/10 Excellent

Justin

A hotel with a swimming pool, outdoor seating, and a brick facade.

Residence Inn by Marriott Waldorf

Waldorf

10/10 Excellent

We were turned away by another hotel chain that accepts pets in some locations, but apparently not in Waldorf (not clear on their corporate website). After driving 9+ hours and arriving at 10:30 pm, their manager wouldn't accommodate or make an acception. IMAGINE OUR PLEASURE when greeted kindly & warmly by the staff at Reaidence Inn,where we were upgraded to a 2bd suite at no extra charge when it was discovered the room Id frantically booked online was unavailable! HIGHLY recommend this hotel...

Deirdre

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, 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.

Find Hotels with a Pool in Chesapeake Beach, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chesapeake Beach hotels with a pool

1. Rod 'N' Reel Resort

2. Holiday Inn Express Prince Frederick by IHG

3. Anchored Inn at Hidden Harbour Marina

4. Springhill Suites by Marriott Prince Frederick

5. Knapps Narrows Marina & Inn

6. The Inn at Tacaro Estate

7. Inn at Perry Cabin

8. Wylder Tilghman Island

9. St Michaels Inn

10. Sonesta ES Suites Annapolis

Choose what matters most at hotels with a pool in Chesapeake Beach

Top Chesapeake Beach Hotel Reviews

Rod 'N' Reel Resort

10/10 Excellent

Frequently Asked Questions

What are some hotels with pools in Chesapeake Beach?

What is there to see and do in Chesapeake Beach?

When is the best time to book a hotel with a pool in Chesapeake Beach?