Find Hotels with a Pool in Royal Oak, MD

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Royal Oak Hotels with a Pool

Our top choices for Royal Oak hotels with a pool

Seasonal outdoor pool
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 ￥21,032
￥29,990 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wylder Tilghman Island
Indoor pool
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 star property
Cambridge
8.2 out of 10, Very Good, (793)
"It was a nice comfortable room convenient to our travels and at a great price. "
United States
Ann
The price is ￥16,695
￥18,531 total
includes taxes & fees
Dec 28 - Dec 29
Comfort Inn & Suites Cambridge
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1000)
"clean and comfy, friendly staff"
United States
Tamara
The price is ￥17,237
￥18,960 total
includes taxes & fees
Jan 4 - Jan 5, 2026
St Michaels Inn
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is ￥20,064
￥27,779 total
includes taxes & fees
Dec 11 - Dec 12
Kent Island Resort
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is ￥18,818
￥20,700 total
includes taxes & fees
Dec 12 - Dec 13
Knapps Narrows Marina & Inn
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is ￥13,554
￥15,045 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
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 ￥16,566
￥21,504 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Rod 'N' Reel Resort
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
7.6 out of 10, Good, (825)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ￥12,580
￥13,838 total
includes taxes & fees
Dec 21 - Dec 22
Quality Inn
Lobby
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

2.5 star property
Grasonville
7.8 out of 10, Good, (859)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ￥13,330
￥14,797 total
includes taxes & fees
Dec 14 - Dec 15
Quality Inn Grasonville near Kent Island
Outdoor pool
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 ￥20,891
￥23,817 total
includes taxes & fees
Dec 29 - Dec 30
Anchored Inn at Hidden Harbour Marina
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.
View all properties

Top Royal Oak Hotel Reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience. "
Drexel 1-night trip
Posted 5 days ago
Hyatt Regency Chesapeake Bay

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Royal Oak?
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS): Features sun loungers, a pool, and complimentary wireless internet access. Hyatt Regency Chesapeake Bay: Offers kitchens, a communal pool, and televisions. Rod 'N' Reel Resort: Provides 2 outdoor pools, a children's pool, and a private beach. St Michaels Inn: Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. Hyatt Place Kent Narrows & Marina: Offers daily, a seasonal outdoor pool, and free self parking.
What is there to see and do in Royal Oak?
Make a point to visit attractions like Chesapeake Bay Maritime Museum and Phillips Wharf Environmental Center. Discover sights such as Saint Michaels Village, St. Michaels Winery, and St. Michaels Marina during your stay.
When is the best time to book a hotel with a pool in Royal Oak?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Royal Oak in the hottest months of July, August, or June when the average temp is 75°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 41°F.