Photo by Ronanne Vinson

Find Hotels with a Pool in Chesapeake Beach, MD

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Beach Hotels with a Pool

Check prices for these dates

Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Chesapeake Beach Hotels with a Pool

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

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very Good, (1000)
"Great place to stay."
$156 nightly
The price is $172
Aug 7 - Aug 8
Total includes taxes and fees
Rod 'N' Reel Resort
St Michaels Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"Great spot to be close to town for a modest price. "
$96 nightly
The price is $106
Sep 2 - Sep 3
Total includes taxes and fees
St Michaels Inn
Inn at Perry Cabin
Outdoor pool

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (356)
"Beautiful place to stay."
$648 nightly
The price is $713
Sep 1 - Sep 2
Total includes taxes and fees
Inn at Perry Cabin
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (129)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
$229 nightly
The price is $252
Aug 6 - Aug 7
Total includes taxes and fees
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
$243 nightly
The price is $267
Aug 6 - Aug 7
Total includes taxes and fees
George Brooks House B&B
Knapps Narrows Marina & Inn
Seasonal outdoor pool

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (338)
"Our room overlooked the channel at Knapp's Narrows. The staff is friendly and helpful. We will definitely stay here again."
$220 nightly
The price is $242
Aug 28 - Aug 29
Total includes taxes and fees
Knapps Narrows Marina & Inn
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (57)
"Good service and good options to enjoy the stays. "
$211 nightly
The price is $232
Aug 18 - Aug 19
Total includes taxes and fees
Wylder Tilghman Island
The Tilghman Island Inn
Seasonal outdoor pool, pool umbrellas

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (98)
"Beautiful location on the water. The staff are super nice and helpful. The restaurant is very good. We had an excellent house smoked pulled pork sandwich and a shrimp po boy."
$205 nightly
The price is $226
Aug 24 - Aug 25
Total includes taxes and fees
The Tilghman Island Inn
Hilton Garden Inn Solomons
Outdoor pool

Hilton Garden Inn Solomons

3.0 star property
8.6 out of 10, Excellent, (610)
"Convenient location and next to a good restaurant and brewery."
$129 nightly
The price is $143
Aug 31 - Sep 1
Total includes taxes and fees
Hilton Garden Inn Solomons
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
Pool

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

10.0 out of 10, Exceptional, (2)
"This house is in a prime location. Sweet neighborhood on the Bay. The house itself has a great dock that provides constant activities for kids. The pool was clean and situated with a stunning view. The house has so many sleeping options and can accommodate large groups. The proximity to downtown Annapolis allows for frequent excursions. Property mgt very good. Highly recommend renting!"
$1,096 nightly
The price is $1,249
Aug 18 - Aug 19
Total includes taxes and fees
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
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.

Top Chesapeake Beach Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Great options"
NORMA 1-night trip
Posted 2 days ago
Rod 'N' Reel Resort

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. SpringHill Suites by Marriott Annapolis: Offers a snack bar/deli, an indoor pool, and daily. Sonesta ES Suites Annapolis: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. Econo Lodge Andrews Air Force Base: Provides a full-service spa, an outdoor pool, and 2 bars. Wingate by Wyndham Waldorf/Washington DC Area: Features a snack bar/deli, a seasonal outdoor pool, and full.
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, Breezy Point Beach, and Bruce Gabrielson's Surf Art Gallery and Museum. 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.