The Best Hotels with a Pool in Tilghman, MD from ￥14,273 in 2026

Q: What are some accommodations with pools in Tilghman?

The Tilghman Island Inn : Inn, 4-minute walk from Chesapeake Bay. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Wylder Tilghman Island : Hotel, 8-minute walk from Chesapeake Bay. Offers a private beach, a seasonal outdoor pool, and a sauna. Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets : Features 2 outdoor pools, a children's pool, and a private beach. Hyatt Regency Chesapeake Bay : Hotel, 1-minute walk from Chesapeake Bay. Offers a seasonal outdoor pool, an indoor pool, and 2 restaurants. Rod 'N' Reel Resort : Features a full-service spa, an outdoor pool, and 2 bars.

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Our top choices for Tilghman hotels with a pool

Wylder Tilghman Island

Tilghman

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

￥61,321 total

includes taxes & fees

Jun 2 - Jun 3

Days Inn & Suites by Wyndham Cambridge

Cambridge

Dive into seasonal outdoor pool bliss at this Cambridge retreat for adult relaxation.

￥14,273 total

includes taxes & fees

Jun 10 - Jun 11

Quality Inn Grasonville near Kent Island

Grasonville

Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.

￥18,781 total

includes taxes & fees

Jun 15 - Jun 16

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St. Michaels

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

￥21,803 total

includes taxes & fees

Jun 23 - Jun 24

Best Western Kent Narrows Inn

Grasonville

Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.

￥20,342 total

includes taxes & fees

Jun 15 - Jun 16

Knapps Narrows Marina & Inn

Sherwood

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

￥26,277 total

includes taxes & fees

Jun 1 - Jun 2

Quality Inn

Easton

Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.

￥17,718 total

includes taxes & fees

Jun 25 - Jun 26

Kent Island Resort

Stevensville

Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.

￥32,967 total

includes taxes & fees

Jun 15 - Jun 16

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Choose what matters most at hotels with a pool in Tilghman

Breakfast included

4 stars

Top Tilghman Hotel Reviews

Days Inn & Suites by Wyndham Cambridge

2/10 Terrible

"I booked this place last minute just to spend a quick night after a change of plans in our trip due to weather. The place is simply disgusting. Don’t stay here. I never thought a Wyndham branded property could be this filthy. Shame on them for not verifying the basic cleanliness of a hotel they allow to use their name."

Best Western Plus Easton Inn & Suites

6/10 Okay

"The property felt outdated (still had thermometers hanging on the wall from COVID) . The hot tub was disgusting- looked like mold on the benches. Only partly filled and freezing, the jets were not producing bubbles- there was no sign saying it was out of order. The blankets on the bed had literal holes in them. There was no toaster in the breakfast area for the bagels, toast, etc. The windows in the pool area were opened so as the night went on, it was getting colder because of the outside temp. There did not seem to be drainage in the pool area because there was so much pooling of water on the ground. Not enough towels in the bathroom. The staff was not super helpful/friendly. The AC was very noisy. The location is convenient but the hotel itself was not great."

Hyatt Regency Chesapeake Bay

8/10 Good

"Hotel is beautiful , grounds are beautiful ! Staff is amazing ! Only disappointment was the pool situation - Seems like if you are there during the week or if weather isn’t perfect restaurants and amenities aren’t available as expected. It wasn’t raining just overcast, and it was warm and humid out but outdoor pools closed 80% of our three days bc “short staffed,” “broken heater “ or “ the rain the days prior made the pool water cold.” No activities or events during the weekdays for kids or adults , Just saying :( No glow golf for kids , asked about it a few times. But beautiful place and wonderful staff! Would try it again ! Only one restaurant Open for breakfast all three days."

Frequently asked questions

What are some accommodations with pools in Tilghman?

The Tilghman Island Inn: Inn, 4-minute walk from Chesapeake Bay. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Wylder Tilghman Island: Hotel, 8-minute walk from Chesapeake Bay. Offers a private beach, a seasonal outdoor pool, and a sauna. Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets: Features 2 outdoor pools, a children's pool, and a private beach. Hyatt Regency Chesapeake Bay: Hotel, 1-minute walk from Chesapeake Bay. Offers a seasonal outdoor pool, an indoor pool, and 2 restaurants. Rod 'N' Reel Resort: Features a full-service spa, an outdoor pool, and 2 bars.

What is there to see and do in Tilghman?

Make a point to visit attractions like Northern Chesapeake Bay and Phillips Wharf Environmental Center. During your stay, check out sights such as Tilghman Island Marina, Chesapeake Bay, and Tilghman Watermen's Museum. Take in the natural beauty of Tilghman with the island views and sunsets.

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

You may want to consider a place to stay with an outdoor swimming pool if you plan to visit Tilghman in the hottest months of July, August, or June when the average temp is 75°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 41°F.

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