Find Hotels with a Pool in Winchester, MD

Booking hotels with pools in Winchester on Expedia

Your dream vacation is just a few clicks away thanks to Expedia's amazing selection of hotels with pools in Winchester. Finding them is as easy as lazing on a lounge chair thanks to the easy-to-use search wizard. All you need to do is select your dates and it'll return hundreds of fantastic options. With so many options to choose from, the filters come in handy as they let you tailor your search results based on your preferences. 

If it's luxury you're seeking, select the “5-star” filter. From infinity pools that seem to blend into the horizon to swim-up bars where you can sip on margaritas in the water, this filter will show you the most opulent accommodations available. The “guest rating” filter will help you pin down Expedia's top-rated Winchester hotels with a pool based on hundreds of reviews from fellow travelers. Once you've found your dream property, click through to choose your room and book. The detailed hotel descriptions on Expedia, including things like room size, cancellation policy, and info about the all-important swimming pool, means you'll know exactly what to expect when you arrive.  

Kid-friendly Winchester hotels with a pool

Get ready to blow up the inflatable pool floats and swimming tubes, as you'll find a multitude of kid-friendly Winchester hotels with a pool on Expedia. Select the “family-friendly” search filter to scan these. From splashing with mom and dad to playing around on pool noodles, your kids will love nothing more than long, sunny days in the water. Many family-friendly hotels boast children's pools with shallow water and dedicated lifeguards too, so you can rest assured your little ones are safe while playing.  

Some hotels with pools also offer kids' clubs with fun activities and events to keep your youngsters entertained all day long. They'll be able to make new friends, learn how to swim, and play classic games like water volleyball and pool tag. Best of all, with your kids kept entertained, you'll be able to enjoy some well-earned “me time”. It's worth looking for all-inclusive plans, too. These make for a hassle-free family vacation as they include all meals and drinks, so you won't have to worry about eating out or cooking. Many family-friendly hotels even offer children's menus with your kids' favorite foods.  

Winchester spa hotels with pools

Click both the “pool” and “spa” filters on Expedia to view some of the best Winchester spa hotels with pools. Picture yourself receiving a full body massage, easing the knots out of your back before diving into the refreshing water. The dreamy combination of therapeutic swimming and holistic spa treatments means you'll come back from vacation relaxed and glowing. Many hotels even offer hot tubs and wellness activities, like poolside yoga and meditation.  

Plan your pool hotel stay in Winchester

When looking for Winchester hotels with swimming pools in 2025, it's worth researching which area you'd like to stay in. You can choose to be close to key attractions or in more distant places for something more secluded. Wherever you opt for, the “popular locations” and “neighborhood” filters make it a breeze to find hotels with pools in Winchester's most popular areas. There are more than just hotels, too. Take advantage of the “property type” filter to view vacation homes with pools in Winchester, including villas, condos, and private homes.