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

Hotels with Swimming Pool in Tilghman, Maryland

  • 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 Swimming Pool

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 large building with a swimming pool, dock, and green surroundings.
A spacious indoor dining area with large windows, tables, and chairs.

1. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
P11,578
P12,735 total
includes taxes & fees
Oct 1 - Oct 2
The Tilghman Island Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A waterfront hotel with a covered dock and a large building with multiple balconies.
A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.

2. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
P13,687
P18,184 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 building with a sign reading "The Inn."
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.
P9,074
P9,982 total
includes taxes & fees
Oct 27 - Oct 28
Knapps Narrows Marina & Inn
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
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.

4. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
P5,573
P6,130 total
includes taxes & fees
Oct 4 - Oct 5
St Michaels Inn
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

5. 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.
P9,048
P12,128 total
includes taxes & fees
Oct 8 - Oct 9
Rod 'N' Reel Resort
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A gym with a treadmill, elliptical, and stationary bike.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

6. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.
P5,573
P6,131 total
includes taxes & fees
Oct 15 - Oct 16
Baymont by Wyndham Easton
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

7. 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.
P8,073
P8,880 total
includes taxes & fees
Oct 1 - Oct 2
Best Western Plus Easton Inn & Suites
A swimming pool with blue lounge chairs and a building with balconies in the background.
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.
A marina with docked boats, a picnic area, and a grassy lawn with a tree.
A modern kitchen with a large island, bar stools, and a wine rack.

8. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
  • Pool paradise meets scenic marina views for a refreshing escape on the water.
P12,468
P14,214 total
includes taxes & fees
Oct 7 - Oct 8
Anchored Inn at Hidden Harbour Marina
A swimming pool with clear water, surrounded by walls with arched windows and a tiled floor.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.
A hotel room with a large bed, bedside tables, a desk, a chair, a flat-screen TV, and a window with a view.
A Holiday Inn Express hotel with a brick facade, a central entrance, and a parking lot with several cars.

9. Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG
Prince Frederick
  • Dive into a refreshing indoor pool sanctuary with year-round swimming at this conveniently located hotel in Prince Frederick.
P7,385
P8,892 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Express Prince Frederick by IHG
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.
A lobby with two yellow armchairs, a glass-top coffee table, a lamp, and a decorative bamboo wall.
A hotel with a brick facade, a covered entrance, and a sign reading "Springhill Suites."
A hotel lobby with a reception desk, a glass-top table with a bowl, potted plants, a vending machine, and a large window.

10. Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick
Prince Frederick
  • Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.
P7,394
P8,207 total
includes taxes & fees
Oct 4 - Oct 5
Springhill Suites by Marriott Prince Frederick
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

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."
Christina 2-night trip
Posted 22 hours ago
Inn at Perry Cabin
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Pet friendly. Full breakfast. Desk was accommodating for a ground floor room for my dog. Room was clean and comfortable."
Wayne 1-night trip
Posted 7 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

8/10 Good
"The property was ok. The room was clean and served its purpose. They do offer free breakfast. I would not call what I had breakfast. Cold eggs and a stale muffin. So for the price you it was not worth it."
David 1-night trip
Posted 10 days ago
Springhill Suites by Marriott Prince Frederick

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