Holiday rentals with a pool in Germantown

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Germantown

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

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Guest favourite

Cottage in Hamilton

4.95 out of 5 average rating, 346 reviews

*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

Guest favourite

Guesthouse in Middletown

5 out of 5 average rating, 112 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 favourite

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 favourite

Home in Harpers Ferry

4.97 out of 5 average rating, 179 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

Nestled in the Blue Ridge Mountains of West Virginia, this lovingly restored 1800s farmhouse and barn studio is the perfect blend of historic charm and modern convenience. Relax in our year-round heated saltwater plunge pool. Ideal for groups, the farmhouse is just minutes from hiking trails, vineyards, and breweries. Conveniently located only an hour from Baltimore and DC, and within easy reach of Philadelphia and NYC. Follow @perennialstays for exclusive details and behind-the-scenes.

Guest favourite

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 favourite

Guest suite in Catonsville

4.94 out of 5 average rating, 501 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Guest favourite

Cottage in Harpers Ferry

4.95 out of 5 average rating, 219 reviews

Harper's Ferry Tree House/ hot tub / nature/ trees

Cozy cabin in a private community minutes away from downtown Harper's Ferry. This cottage in the trees is situated on a private wooded road and has parking for 5 vehicles. You'll enjoy a large deck, inflatable hot tub, outdoor fire pit, and gated access to a beautiful picnic area with canoe/kayak/swim spot on east side of Shenandoah River. If you are interested in fishing/boating/tubing/swimming this spot cannot be beat . Ride the commuter train to DC to take in the sites. Enjoy!

Guest favourite

Home in Fairfax

4.96 out of 5 average rating, 163 reviews

6BR Modern Home w/HEATED Pool & Screened in Porch

Pool/Hot Tub open all year round! Beautiful modern house only 5 minutes from 495 and 20 minutes to Washington DC. New saltwater HEATED Pool with hot tub and tanning ledge. Fantastic Tec heat mirror glass grill in the screened-in porch with commercial-grade vents to clear the smoke. Shopping center with Trader Joe's and Total Wine 2 minutes away. Perfect family home for reunions or vacations. This is not a party or events house. We require guests to have positive reviews to book.

Guest favourite

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 favourite

Guesthouse in Highland

4.98 out of 5 average rating, 277 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

Guest favourite

Farm stay in Purcellville

4.97 out of 5 average rating, 156 reviews

The Hunt Box @ Tally Yo Farm

This is a residence above a 5-stall horse barn. A two bedroom house with 2 bath, Juliette balcony, great views, vaulted ceilings, fully appointed kitchen, laundry, 6 acre farm. Beautifully decorated in traditional English equestrian decor, with homage to the Northern Virginia hunts located just a stone's throw away. Pool open 5/15-10/15. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs.

Guest favourite

Home in Sabillasville

4.92 out of 5 average rating, 106 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!