Photo by Ronanne Vinson

Hotels with Swimming Pool in Chesapeake Beach, Maryland

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Beach Hotels with Swimming Pool

Next weekend
In two weeks

Top Chesapeake Beach Hotels with Swimming Pool

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (342)
"Beautiful view!"
The price is P5,787
P6,366 total
includes taxes & fees
Oct 6 - Oct 7
Knapps Narrows Marina & Inn

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1002)
"Great location, free parking, free breakfast excellent staff."
The price is P5,514
P6,066 total
includes taxes & fees
Oct 19 - Oct 20
St Michaels Inn

Legacy Villa

4.0 star property
The price is P9,730
P10,995 total
includes taxes & fees
Oct 14 - Oct 15
Legacy Villa

Rod 'N' Reel Resort

4.0 star property
8.4 out of 10, Very Good, (1001)
"great place "
The price is P7,760
P9,771 total
includes taxes & fees
Oct 6 - Oct 7
Rod 'N' Reel Resort

Holiday Inn Express Prince Frederick by IHG

2.5 star property
8.8 out of 10, Excellent, (671)
"Will be stay again soon "
The price is P5,498
P6,745 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express Prince Frederick by IHG

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (82)
"Very relaxing stay."
The price is P9,896
P13,432 total
includes taxes & fees
Oct 12 - Oct 13
Wylder Tilghman Island

Springhill Suites by Marriott Prince Frederick

3.0 star property
8.6 out of 10, Excellent, (917)
"clean, quiet and helpful staff."
The price is P6,121
P6,795 total
includes taxes & fees
Nov 2 - Nov 3
Springhill Suites by Marriott Prince Frederick

Hilton Garden Inn Solomons

3.0 star property
8.6 out of 10, Excellent, (627)
"Nice Stay"
The price is P7,361
P8,171 total
includes taxes & fees
Oct 12 - Oct 13
Hilton Garden Inn Solomons

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (456)
"The view from the balcony is the best, whether at night or the day time. The outside bar everyone is so friendly. I have stayed here a few times and every time I come to the area, I will only stay here. I highly recommend it !"
The price is P10,365
P11,816 total
includes taxes & fees
Oct 6 - Oct 7
Anchored Inn at Hidden Harbour Marina

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (64)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is P11,458
P12,604 total
includes taxes & fees
Oct 6 - Oct 7
George Brooks House B&B
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

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. SpringHill Suites by Marriott Annapolis: Provides a snack bar/deli, an indoor pool, and daily. St Michaels Inn: Features daily, a seasonal outdoor pool, and free self parking. The Wildset: Offers 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 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.