A group of white birds flying over a field of dry grass.

Find Hotels with a Pool in Woolford, 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 Woolford Hotels with a Pool

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Woolford hotels with a pool

A large indoor swimming pool with clear water, tiled walls, and a ceiling with ventilation ducts.
A breakfast buffet with various food items and a sign indicating complimentary breakfast hours.
A coffee station with two espresso machines, a coffee grinder, and various coffee pods and cups.
A bathtub with a showerhead, grab bar, and a shelf with toiletries.

1. Holiday Inn Express Cambridge by IHG

Holiday Inn Express Cambridge by IHG
Cambridge
  • Splash into relaxation with a rejuvenating indoor pool and hot tub retreat at this Cambridge hotel.
₩158,776
₩176,242 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Cambridge by IHG
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.
A marina with boats docked, a sandy beach, and a clear blue sky.

2. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Aquatic paradise awaits with 2 outdoor pools, indoor pool, and waterslide offering year-round relaxation at this riverside resort.
₩253,508
₩325,839 total
includes taxes & fees
Nov 10 - Nov 11
Hyatt Regency Chesapeake Bay
A swimming pool with a 5ft depth marker, white lounge chairs, and tables arranged around the pool area.
A hotel room with a desk, chair, blue sofa, ottoman, and a hallway leading to a door.
A spacious lobby with a reception desk, seating area, and a television screen.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

3. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
₩146,888
₩163,046 total
includes taxes & fees
Oct 28 - Oct 29
Comfort Inn & Suites Cambridge
A swimming pool with a fenced area, lounge chairs, and a covered seating area.
A compact kitchenette with a microwave, coffee maker, and storage for condiments.
A bathroom with a white sink, a mirror, a towel rack, and a toilet.
A hotel room with a blue accent wall, a large bathtub, a sofa, a bed with a patterned bedspread, and a television.

4. Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge
Cambridge
  • Dive into seasonal outdoor pool bliss at this Cambridge retreat for adult relaxation.
₩100,936
₩112,040 total
includes taxes & fees
Nov 1 - Nov 2
Days Inn & Suites by Wyndham Cambridge
A swimming pool with metal railings, a tiled deck, and a white building with windows.
A covered outdoor seating area with wicker furniture and large windows.
A modern living room with a fireplace, sofas, and a large window.
A hotel lobby with a fireplace, a reception desk, and a seating area.

5. Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
Solomons
  • Dive into serene poolside relaxation at this suburban hotel with a sparkling outdoor pool.
₩168,983
₩187,571 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Solomons
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A hotel hallway with carpeted floors, white doors, and overhead lighting.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

6. Hampton Inn Easton

Hampton Inn Easton
Easton
  • Dive into refreshing luxury at this Easton hotel with a pristine indoor pool and fitness center for your aquatic escape.
₩170,624
₩187,689 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Easton
A swimming pool with multiple people swimming and lounging around.
A covered patio area with wicker furniture and a view of a building with large windows.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.
A waterfront property with houses, a dock, and a grassy area.

7. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
₩200,138
₩220,152 total
includes taxes & fees
Oct 29 - Oct 30
Knapps Narrows Marina & Inn
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A room with a view of a wooden deck and a gazebo by the water.
A white house with a garden patio featuring a wicker chair and a round table.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.

8. 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.
₩708,487
₩779,336 total
includes taxes & fees
Nov 3 - Nov 4
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 hotel room with two beds, a chair, and a painting on the wall.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

9. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
₩106,873
₩117,561 total
includes taxes & fees
Nov 1 - Nov 2
St Michaels Inn
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.

10. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
₩587,203
₩645,923 total
includes taxes & fees
Oct 18 - Oct 19
The Oaks Waterfront
View all properties

Choose what matters most at hotels with a pool in Woolford

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Woolford Hotel Reviews

St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 16 hours ago
St Michaels Inn
Hampton Inn Easton

Hampton Inn Easton

10/10 Excellent
"Pet friendly...very nice for our dog Staff helpful"
Andrew 3-night trip
Posted 1 day ago
Hampton Inn Easton
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

8/10 Good
"The room was clean and away from the elevators with no issues for the specific room. The only reason this is not a 5 star review is that there is no accommodation for customers / guests that need a nightstand on both sides of the bed. In our situation both customers have a CPAP machine. The reservation was for 2 guests and the room was a queen bed and upon arrival we had to decide who was going to sleep without their CPAP machine because the room has no bedside table or electrical outlets on the outer edge of the bed. Regardless of the medical need when will Hotels learn that both sides of the bed need a place to hold their CPAP or book or tea."
Christina 1-night trip
Posted 2 days ago
Hilton Garden Inn Solomons
The Tidewater Inn

The Tidewater Inn

8/10 Good
"This hotel is a gorgeous historic hotel. It has all character and beauty that you expect in Easton, Maryland. People should be aware that the air conditioning/heat is controlled by the staff. So if it’s hot in the room, you can’t adjust the air conditioning."
Elena 2-night trip
Posted 2 days ago
The Tidewater Inn
Baymont by Wyndham Easton

Baymont by Wyndham Easton

10/10 Excellent
"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."
Edwin 1-night trip
Posted 6 days ago
Baymont by Wyndham Easton

Frequently asked questions

What are some hotels with pools in Woolford?
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. The Tidewater Inn: Offers daily, a seasonal outdoor pool, and free self parking. Days Inn & Suites by Wyndham Cambridge: Features a full-service spa, an outdoor pool, and 2 bars. Inn at Perry Cabin: Offers buffet, an indoor pool, and free self parking.
What is there to see and do in Woolford?
Surround yourself with nature at Blackwater National Wildlife Refuge. Discover sights such as Woods Island 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