The Best Hotels with a Pool in Woolford, MD from NT$2,817 in 2026

Q: What are some hotels with pools in Woolford?

Hyatt Regency Chesapeake Bay : Offers 2 outdoor pools, a children's pool, and a private beach. St Michaels Inn : Provides daily, a seasonal outdoor pool, and free self parking. Inn at Perry Cabin : Features a full-service spa, an outdoor pool, and 2 bars. The Wildset : Offers a snack bar/deli, an outdoor pool, and complimentary wired internet access. The Tidewater Inn : Provides daily, a seasonal outdoor pool, and complimentary wired internet access.

Birds - Cattle Egret, Blackwater National Wildlife Refuge, Virginia

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 Woolford Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Woolford hotels with a pool

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.

NT$4,683 total

includes taxes & fees

Jun 8 - Jun 9

Days Inn & Suites by Wyndham Cambridge

Cambridge

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

NT$2,817 total

includes taxes & fees

Jun 21 - Jun 22

Knapps Narrows Marina & Inn

Sherwood

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

NT$5,192 total

includes taxes & fees

Jun 7 - Jun 8

Quality Inn Solomons - Beacon Marina

Solomons

Dive into serenity at this marina-side retreat with a seasonal outdoor pool and relaxing hot tub experience.

NT$3,552 total

includes taxes & fees

Jun 28 - Jun 29

Holiday Inn Express Cambridge by IHG

Cambridge

Splash into relaxation with a rejuvenating indoor pool and hot tub retreat at this Cambridge hotel.

NT$4,715 total

includes taxes & fees

Jun 21 - Jun 22

Hilton Garden Inn Solomons

Solomons

Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.

NT$4,554 total

includes taxes & fees

Jun 29 - Jun 30

Comfort Inn & Suites Cambridge

Cambridge

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

NT$4,571 total

includes taxes & fees

Jun 7 - Jun 8

Hampton Inn Easton

Easton

Dive into refreshing luxury at this Easton hotel with a pristine indoor pool and fitness center for your aquatic escape.

NT$5,057 total

includes taxes & fees

Jun 21 - Jun 22

View all properties

Choose what matters most at hotels with a pool in Woolford

Breakfast included

4 stars

Top Woolford Hotel Reviews

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

10/10 Excellent

"I am satisfied and excited"

The Tidewater Inn

8/10 Good

"I have stayed at this hotel twice and the staff is absolutely lovely. They are warm and welcoming. The hotel is very clean and comfy and it is very conveniently located. Both times we attended a show at the Avalon Theater, which is right across the street and it is wonderful to leave a show and have the hotel two minutes away. However, we paid over $300 for one night and breakfast is not included in the price. Plus, we were not able to park in the parking lot behind the hotel because it was full and we had to find street parking. The rooms do not have refrigerators. The bathrooms are very small. I am not a large person and the shower was a very tight fit for me. It must be very uncomfortable for a full-size human."

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."

Frequently asked questions

What are some hotels with pools in Woolford?

Hyatt Regency Chesapeake Bay: Offers 2 outdoor pools, a children's pool, and a private beach. St Michaels Inn: Provides daily, a seasonal outdoor pool, and free self parking. Inn at Perry Cabin: Features a full-service spa, an outdoor pool, and 2 bars. The Wildset: Offers a snack bar/deli, an outdoor pool, and complimentary wired internet access. The Tidewater Inn: Provides daily, a seasonal outdoor pool, and complimentary wired internet access.

What is there to see and do in Woolford?

The picturesque setting of Blackwater National Wildlife Refuge and Woods Island showcase the area's natural beauty. Discover sights such as Harriet Tubman Underground Railroad National Historical Park, Harriet Tubman Museum and Educational Center, and Choptank River Lighthouse during your stay.

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

You may want to think about an accommodation with an outdoor swimming pool if you're planning to visit Woolford in the hottest months of July, August, or June when the average temp is 75°F. Lodging offering an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temperature is 41°F.

Explore a world of travel with Expedia

Book Hotels with a Pool in Woolford on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Woolford Hotels with a Pool