Vacation rentals with a pool in Jefferson County

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Top-rated rentals with a pool in Jefferson County

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Guest favorite

Rental unit in Bluemont

4.95 out of 5 average rating, 297 reviews

A Great Getaway — Foxglove Retreat

Nestled in the Blue Ridge Mountains, "Foxglove Retreat" offers you complete privacy and beautiful vista views of the Shenandoah Valley. Equipped with all the necessities for a relaxed and luxurious experience, the "Foxglove Retreat" is sure to become one of your favorite destinations. "Foxglove Retreat" is ideally located near popular tourist destinations, restaurants and wineries. The Bears Den Trail Center is walking distance for those who would like to explore the beauty of the Blue Ridge Mountains on foot. For those who seek nearby shopping and sightseeing, the quaint village of Middleburg is to the southeast and has many antique shops and elegant boutiques nestled in its historic buildings. To the east is the town of Leesburg featuring the upscale Leesburg Corner Premium Outlets and the Leesburg Farmers’ Market. To the west is the Old Town of Winchester where you will discover charming shops, restaurants, galleries, centuries-old architecture, and historical landmarks.

Guest favorite

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 favorite

Cabin in Hedgesville

4.94 out of 5 average rating, 154 reviews

Hot Tub, Dog Friendly Boho Cabin in The Woods

Get cozy at our secluded A-frame cabin in The Woods! Feel transported into the trees as you enjoy coffee on the screened-in porch, cuddle next to the wood burning fire, relax in the hot tub, or simply look out the expansive windows. Furry friends will feel at home with a custom-built dog bowl station and two-acres for exploring. Just under two hours from the D.C./Baltimore area with a ChargePoint EV station in the driveway, it's the perfect all-seasons getaway for families and groups of friends.

Guest favorite

Cabin in Hedgesville

4.92 out of 5 average rating, 234 reviews

Bear Pines Retreat ~ Game Room ~ Screened Porch

Come enjoy this 3 bedroom/2 bath A frame cabin in The Woods. Bear Pines Retreat features 2 bedrooms on the lower level with 4 beds and full bathroom. The Master Suite loft has a queen bed with mountain spa bathroom. You can connect to the built in Bluetooth speaker and play some relaxing music while looking out the skylight above. The living area has plenty of seating with wood burning fireplace and 55” TV mounted above. You can enjoy over 100 cable channels, music and streaming services.

Guest favorite

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 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

Cabin in Hedgesville

4.95 out of 5 average rating, 115 reviews

Starcatcher Chalet, The Woods Resort

Enjoy a fun, relaxing stay at our completely renovated chalet in The Woods Resort in beautiful Berkeley County, WV--a 90-minute drive from the Washington DC-Baltimore Metro Area. You'll be in the heart of the WV Eastern panhandle, close to Sleepy Creek, Berkeley Springs, Cacapon State Park, Antietam National Battlefield, and more. The Woods Resort amenities (fees apply) include a spa, restaurant, and two golf courses, three swimming pools, tennis, pickleball, fitness, and a playground.

Guest favorite

Chalet in Berkeley Springs

4.96 out of 5 average rating, 150 reviews

EVeNTS~Dec 6 Cocoa Crawl~Dec12-15 Christmas Market

WELCOME to BE STILL, our Flagship mountain getaway! Homegrown Hospitality is proud to share our cabin at BerkeleySpringsWVVacations where we are passionate about making our hospitality truly WV Homegrown. This top ranked cabin has 5 large bedrooms, 5 Full baths and one 1/2 bath on 2 wooded acres with private hot tub, pool table, games, 3 porches, campfire under the stars and the kiddos will LOVE our bunk room. ONLY 4 miles to downtown BERKELEY SPRINGS, WV. Americas #9 TOP Small town!

Guest favorite

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 favorite

Cottage in Bluemont

4.95 out of 5 average rating, 230 reviews

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May1- Sept 14. PRIVATE 3 hours pool time daily. Plus private patio, grill and fire pit! Horses outside every window! The Cottage is located on a 230 acre horse farm. Red Gate Farm is a full-service, upscale equestrian farm, containing the Cottage, original farm house and 50 horses & ponies. Convenient to Middleburg and Purcellville, you are surrounded by mountains, wineries, breweries, and hiking, with horses right at your doorstep. All in the beautiful town of Bluemont.

Guest favorite

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!

Superhost

Cabin in Hedgesville

4.9 out of 5 average rating, 163 reviews

Stocked Kitchen w Fireplace and Opt. Pool Access

The perfect getaway for small families or a friendly retreat! A well stocked kitchen, screened gazebo and spacious deck with a retractable gates and wide stairs leading to a fire pit area make this cozy home an outdoor lovers haven! Optional Resort access available to The Woods Resort with indoor and outdoor pools and sports courts, 36 holes of golf and only 10 minutes to public river access. All four seasons are sure to please with hiking and the beauty of West Virginia!