Two people in a red canoe on a body of water with a sunset and a bridge in the background.

Find Hotels with a Pool in Tilghman, MD

  • 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 Tilghman Hotels with a Pool

Tonight
Oct 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Tilghman hotels with a pool

A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
A spacious indoor dining area with large windows, tables, and chairs.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

1. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
₩246,938
₩271,632 total
includes taxes & fees
Oct 19 - Oct 20
The Tilghman Island Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A waterfront property with a covered patio, a dock, and a boat.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.
A waterfront hotel with a covered dock and a large building with multiple balconies.

2. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
₩324,356
₩423,531 total
includes taxes & fees
Oct 18 - Oct 19
Wylder Tilghman Island
A swimming pool with multiple people swimming and lounging around.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.
A covered patio area with wicker furniture and a view of a building with large windows.
A waterfront property with houses, a dock, and a grassy area.

3. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
₩200,220
₩220,242 total
includes taxes & fees
Oct 14 - Oct 15
Knapps Narrows Marina & Inn
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A modern bar area with a long counter and multiple bar stools.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

4. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
  • Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
₩192,992
₩214,221 total
includes taxes & fees
Oct 20 - Oct 21
Rod 'N' Reel Resort
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.
A room with a view of a wooden deck and a gazebo by the water.

5. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
₩684,752
₩753,227 total
includes taxes & fees
Nov 8 - Nov 9
Inn at Perry Cabin
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A hotel room with two beds, a chair, and a painting on the wall.

6. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
₩106,917
₩117,609 total
includes taxes & fees
Nov 1 - Nov 2
St Michaels Inn
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
A hotel with a covered entrance, multiple floors, and a parking lot.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

7. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
  • Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.
₩180,398
₩198,438 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott Easton
An indoor swimming pool with a 'NO LIFEGUARD ON DUTY' sign, lounge chairs, and potted plants.
A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.
A coffee station with two coffee machines and a variety of coffee pods and cups.

8. Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
  • Splashy indoor pool retreat creates a refreshing escape in the heart of Easton.
₩198,885
₩218,773 total
includes taxes & fees
Oct 14 - Oct 15
Holiday Inn Express Easton by IHG
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.

9. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
₩587,445
₩646,190 total
includes taxes & fees
Oct 14 - Oct 15
The Oaks Waterfront
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

10. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
  • Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
₩172,189
₩189,408 total
includes taxes & fees
Oct 14 - Oct 15
Best Western Plus Easton Inn & Suites
View all properties

Choose what matters most at hotels with a pool in Tilghman

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Tilghman Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Tilghman?
Wylder Tilghman Island: Hotel, 8-minute walk from Chesapeake Bay. Features a private beach, a seasonal outdoor pool, and a sauna. The Tilghman Island Inn: Guesthouse, 4-minute walk from Chesapeake Bay. Offers daily, a seasonal outdoor pool, and free self parking. Rod 'N' Reel Resort: Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. St Michaels Inn: Offers daily, a seasonal outdoor pool, and free self parking. Hyatt Regency Chesapeake Bay: Provides 2 outdoor pools, a children's pool, and a private beach.
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 Chesapeake Bay, Tilghman Island Marina, and Knapp's Narrows Marina & Inn. 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.

Explore a world of travel with Expedia