TOP Hotels with Pool in Trappe, MD for 2026

Q: What are some hotels with pools in Trappe?

Hyatt Regency Chesapeake Bay : Features 2 outdoor swimming pools, a children's pool and a private beach. Inn at Perry Cabin : Offers a full-service spa, an outdoor pool and 2 bars. Best Western Plus Easton Inn & Suites : Provides complimentary high-speed (wired) Internet access, an indoor pool and free self parking. The Wildset : Offers daily, a seasonal outdoor pool and free self parking. St Michaels Inn : Features daily, a seasonal outdoor pool and free self parking.

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Our top choices for Trappe hotels with a pool

Quality Inn Grasonville near Kent Island

Grasonville

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

฿3,849 total

includes taxes & fees

3 Jun - 4 Jun

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.

฿4,857 total

includes taxes & fees

15 Jun - 16 Jun

Days Inn & Suites by Wyndham Cambridge

Cambridge

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

฿2,925 total

includes taxes & fees

22 Jun - 23 Jun

Quality Inn

Easton

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

฿3,631 total

includes taxes & fees

24 Jun - 25 Jun

Knapps Narrows Marina & Inn

Sherwood

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

฿5,385 total

includes taxes & fees

7 Jun - 8 Jun

Best Western Plus Easton Inn & Suites

Easton

Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.

฿4,990 total

includes taxes & fees

31 May - 1 Jun

Comfort Inn & Suites Cambridge

Cambridge

Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.

฿4,417 total

includes taxes & fees

31 May - 1 Jun

Best Western Denton Inn

Denton

Poolside retreat with a cosy fireplace lobby and complimentary breakfast makes this Denton stay refreshingly convenient.

฿4,653 total

includes taxes & fees

31 May - 1 Jun

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Choose what matters most at hotels with a pool in Trappe

Breakfast included

4 stars

Top Trappe Hotel Reviews

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"The property felt outdated (still had thermometers hanging on the wall from COVID) .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."

Cambridge Inn

2/10 Terrible

"I did not have a very good experience here and I would never return as I have pictures, but I’m not going to post them my greeting with the guy in the front after I checked in he asked if I was a night worker? He was looking for a night worker. I asked for a non-smoking room the whole place smell like smoke and something really old I go into my room my bathroom has this part hanging down where it feels like someone staring at you the tub, barely drained. There was maybe 10 channels on the TV and most of them weren’t English speaking. I didn’t have a pleasant experience here nor would I ever return the one good experience is the lady that cleans? She is very professional very nice and helpful."