Vacation rentals with a pool in Frederick County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Frederick County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Lovettsville

4.83 out of 5 average rating, 103 reviews

Cozy Hemingway Retreat 3500sfHotTub Pool Tennis Ct

5/6 (6th bedroom has queen sofa bed) Bedrooms furnished w/linens and all your needs 10 private acres in Farm land views of horses Remodeled fully equipped Kitchen w/new appliances 5 full baths w/spa like showers 7 person hot tub 35,000 gallon in ground private pool opens May 25 Private Tennis Court (basic)/Basketball Court 2 Fire pits Picnic area with grills and patio furniture Kiddos play area w/swing sets and slides Large great room/family room 10 acres with 4 acres a forest Dining for 8+

Guest favorite

Farm stay in Middletown

5 out of 5 average rating, 17 reviews

Getaway on the Catoctin

Fox Hollow Farm will give you a much-needed opportunity to hit the reset button. Hike the creek-front trails, climb the hills, picnic with a scenic overlook, stop to admire our horses, or venture out to explore the historic downtown Frederick, breweries, wineries, dairies, and orchards. If you’re a fly fisherman, we have almost a mile and a half of unspoiled Catoctin which is stocked. This is a rare setting for its proximity to historic Frederick and easy travel from Baltimore, DC, or beyond.

Guest favorite

Guesthouse in Middletown

5 out of 5 average rating, 110 reviews

Cottage, Pool, & Breakfast on 100ac Horse Estate

Enjoy the unique opportunity to spend time on a stunning Maryland horse farm and estate with private access to the Appalachian Trail in Maryland's Blue Ridge mountains. Located in historic Middletown, the farm is just 60 miles from downtown DC and 20 minutes west of Frederick. Our lovingly renovated 1900 guest cottage sits above an active mountain spring and beside the estate's main residence. You'll encounter chickens, cattle, horses and abundant wildlife as you hike and explore the property.

Guest favorite

Guest suite in Myersville

4.92 out of 5 average rating, 304 reviews

Harmony Lodge nestled in wooded tranquility!

Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or walk the grounds and enjoy Mother nature. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!

Guest favorite

Place to stay in Frederick

4.85 out of 5 average rating, 82 reviews

Cozy Retreat near shopping and downtown Frederick

You get the entire place for yourself, 7 min drive to downtown Frederick Walkling distance to shopping and restaurants. Full kitchen equipped with all you need to cook or warm up food. Complimentary breakfast, coffee, and ice. Access to walking trails near the Monocacy river, tennis courts, and the community Pool. Furnished with sofa, table for 4, fast internet, Premium TV Services. Private entrance, Patio, and parking. Work space for Travel nurses and professionals. 1 E-Bike, & 1 E-Scooters

Guest favorite

Home in Adamstown

4.97 out of 5 average rating, 66 reviews

Wizard's Escape | Sleeps 15+ | Pool | Escape Room

Wizards and Humans are invited to experience the magic of Wizard's Escape. A magical home with an escape room twist. Immerse yourself in this thrilling themed escape room. Then, spend hours on our magical scavenger hunt throughout the castle to find the 7 cruxes. Ask about Day rentals for your group during weekdays. Weddings and bigger Events and Pool rental are an additional cost. Follow us on Insta or Fb for more videos and pics. Book your favorite Gamekeeper's Hut next door. Link below

Guest favorite

Guesthouse in Monrovia

4.97 out of 5 average rating, 143 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

Guest favorite

Cottage in Middletown

4.94 out of 5 average rating, 18 reviews

Another Adventure Farm

Keep it simple with this peaceful, centrally-located stay. Hagerstown, Frederick, Greenbriar State Park, and restaurants/historic sites are just minutes away. Bring your own horse for trail rides or go on foot to discover the abundance of wildlife around our farm. With over a mile of creek, enjoy swimming and fishing or just the views. Come experience the tranquility of nature in a cozy, comfortable, relaxing, fully renovated house. Outdoor pool access in the summer, at the farm house.

Guest favorite

Home in Leesburg

4.97 out of 5 average rating, 115 reviews

Potomac Overlook Farms: 6 BR, 10 Acre River Estate

Welcome to Potomac Overlook Farms, where comfort meets nature on 10 acres along the Potomac River. Surrounded by wineries, breweries, and historic towns, this 5,000 square foot estate offers access to adventure and relaxation. The spacious home comfortably sleeps 16, with an optional guest house for 5. Please inquire about the guest house at booking. Our property, unfortunately, does not offer wheelchair accessibility. The pool is available for your enjoyment from May 1 to October 1.

Guest favorite

Home in New Market

4.93 out of 5 average rating, 128 reviews

Historic Peace and Plenty Farm: Pool House

Peace and Plenty Farm is a 40+ acre, stunning rural escape located in Frederick County, two miles from Historic New Market, 45 minutes from Gettysburg, and an hour from Baltimore or Washington D.C. Feel free to explore our farm’s trails and hidden gems, play yard games with the family, or swim in our lap pool (open from June through October). Our generous space is suitable for a couple's getaway, a weekend with friends, a family vacation, a working vacation, or a quiet retreat.

Guest favorite

Home in Sabillasville

4.92 out of 5 average rating, 104 reviews

Stoney Spring Overlook

This beautiful mountain farm home has breath taking scenic views of the surrounding Catoctin mountain. There are many nearby outdoor activities, including scenic hikes, mountain biking, Ski Liberty, wineries and the Catoctin zoo. While it is a peaceful get away in the mountains, it is just 30 minutes away from the Frederick, MD and historic Gettysburg, PA. Whether you want to get away from the city or explore more of Maryland, this is the perfect stay for you!

Guest favorite

Guest suite in Hagerstown

4.98 out of 5 average rating, 48 reviews

Private Suite - King Bed, Kitchen, Driveway, Pool

FULLY equipped for LONGER STAYS! RELAX, RECHARGE & ENJOY this lovely, spacious PRIVATE SUITE! LOWER-LEVEL with PRIVATE -- ENTRANCE, POOL(seasonal), BACKYARD with PORCH, and DRIVEWAY. Just 5 min. to interstates 81, 70, Meritus Hospital. Within 20 min. to Antietam Battlefield, 15 min. to C&O Canal, 40 min. to Harpers Ferry, 30 min. to Whitetail Ski Resort & a little over 1 hr. to DC. Close to hiking, shopping, dining, golfing, wineries & conferences.