TOP Hotels with Swimming Pool in Tilghman, MD for 2026

Q: What are some accommodation options with pools in Tilghman?

The Tilghman Island Inn : Guest house, 4-minute walk from Chesapeake Bay. Features daily, a seasonal outdoor pool and free self parking. Wylder Tilghman Island : Hotel, 8-minute walk from Chesapeake Bay. Offers a private beach, a seasonal outdoor pool and a sauna. Hyatt Regency Chesapeake Bay : Offers 2 outdoor swimming pools, a children's pool and a private beach. St Michaels Inn : Features daily, a seasonal outdoor pool and free self parking. Rod 'N' Reel Resort : Hotel, 1-minute walk from Chesapeake Bay. Offers a seasonal outdoor pool, an indoor pool and 2 restaurants.

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

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

Tomorrow

Next weekend

In two weeks

Our top choices for Tilghman hotels with a pool

The Tilghman Island Inn

Tilghman

Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.

₹23,900 total

includes taxes & fees

9 Aug - 10 Aug

Wylder Tilghman Island

Tilghman

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

₹39,847 total

includes taxes & fees

2 Aug - 3 Aug

Knapps Narrows Marina & Inn

Sherwood

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

₹15,934 total

includes taxes & fees

27 Jul - 28 Jul

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.

₹8,707 total

includes taxes & fees

18 Aug - 19 Aug

Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)

Rod 'N' Reel Resort

Chesapeake Beach

Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.

₹22,205 total

includes taxes & fees

19 Aug - 20 Aug

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.

₹11,105 total

includes taxes & fees

6 Aug - 7 Aug

Quality Inn

Easton

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

₹10,745 total

includes taxes & fees

16 Aug - 17 Aug

Springhill Suites by Marriott Prince Frederick

Prince Frederick

Splash into relaxation with a sparkling indoor pool and hot tub at this refreshing retreat.

₹12,348 total

includes taxes & fees

11 Aug - 12 Aug

View all properties

Choose what matters most at hotels with a pool in Tilghman

Breakfast included

4 stars

Top Tilghman Hotel Reviews

Rod 'N' Reel Resort

8/10 Good

"Views"

Kent Island Resort

10/10 Excellent

"Peaceful, The home built in 1820 has so much charm, the additions, porch dining, furnishings, grounds options for gatherings and weddings make this an ideal setting for luxurious events that are at the same time unpretentious. Guests tall and small all can find a sense of home, adventure, and pampering in this one spot! The staff were welcoming, cheerful, kind, and so personable while carrying out duties to maintain a vast property and care for the smallest details of each visitor! The property and people were lovely! Don't miss sunset and sunrise on the extended dock, or from the waters edge gazebo. Swimming is serene in the pool and riding a bike around the property brings out your inner 12 year old. Best 24hrs vacation, just 1.5hrs from home, that I've ever had!"

St Michaels Inn

10/10 Excellent

"Staff was great, room was very clean. Upon reading reviews people said the carpets were gross, there was no carpets in my room, very updated rooms and clean and beautiful. Breakfast was a bit disappointing fruit and bagels and English muffins were about the only options, not sure if this was because it wasn’t the weekend. Other than that would definitely stay again!!"

Frequently asked questions

What are some accommodation options with pools in Tilghman?

The Tilghman Island Inn: Guest house, 4-minute walk from Chesapeake Bay. Features daily, a seasonal outdoor pool and free self parking. Wylder Tilghman Island: Hotel, 8-minute walk from Chesapeake Bay. Offers a private beach, a seasonal outdoor pool and a sauna. Hyatt Regency Chesapeake Bay: Offers 2 outdoor swimming pools, a children's pool and a private beach. St Michaels Inn: Features daily, a seasonal outdoor pool and free self parking. Rod 'N' Reel Resort: Hotel, 1-minute walk from Chesapeake Bay. Offers a seasonal outdoor pool, an indoor pool and 2 restaurants.

What is there to see and do in Tilghman?

Make a point to visit attractions such as Northern Chesapeake Bay and Phillips Wharf Environmental Center. During your stay, visit sights such as Chesapeake Bay, Tilghman Watermen's Museum and Tilghman Island Marina. 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 think about a place to stay that offers an outdoor pool if you'll be visiting Tilghman in the hottest months of July, August or June, when the average temp is 24°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or December, when the average temp is 5°C.

Explore a world of travel with Expedia

More ways to book

Book Hotels with Swimming Pool in Tilghman on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Tilghman Hotels with Swimming Pool