
Holiday rentals with a pool in Jefferson County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Jefferson County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Harpers Ferry Apartment w/ Private Pool & Hot Tub!
Explore Civil War sites, take in the scenery on nearby hikes, or stay home for a pool day when you book this 2-bedroom, 1-bath vacation rental apartment. Located under 2 miles from Downtown Harpers Ferry, and featuring a lovely garden, this hideaway is the ideal spot for your next West Virginia Retreat. While you're here, visiting Harpers Ferry National Historic Park and the Appalachian Trail are a must! If you choose to stay in, the hot tub and tropical bar are great ways to maximize your stay.

An Escape Bordering National Park land 1 mi to C&O
Relax in this serene setting with a hot tub overlooking Harpers Ferry National Park Land. Enjoy evening fires, the pool, screened-in porch, a book in the solarium or go hiking/tubing nearby. We hope our home (Harpers Getaway) provides a tranquil backdrop to immerse you in nature and lower your stress level so you can reconnect with those you love! It is located only 1 mile from the C&O towpath & Potomac River, 2 miles (by foot) from historic Harpers Ferry w/ breweries, wineries galore nearby.

Vineyard View Chalet
Heated Pool! GIANT hot tub, Fireplace with towering stone hearth, private room layout, exquisite master bath with dual soaking tub and Japanese toilet. Peaceful and secluded log home with sweeping views of the vineyard and ridgeline. Relax by the pool, prepare gourmet meals in the well-equipped kitchen and on the deck (pellet smoker and blacktop w/ air fryer). Expansive living areas flooded with light and a lower lvl rec area with a 100" 4k projector, shuffleboard, skeeball, darts, poker.

Rustic Blue Ridge Cabins
Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd of an Acre with access to wooded a trail featuring Cold Springs. Amenities-4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail,Shenandoah River, with restaurants, breweries, distilleries, and wineries close by! These are rustic not luxurious Cabins

Mountaintop Cabin w/ Poolside Sunsets!
MOUNTAIN MAMA VACATION HOMES & CABINS Trying to decide between dramatic views and a poolside escape? How about both! The pool at this mountaintop cabin is perfectly situated to soak in the 100-mile views over the Shenandoah Valley. Once you've had enough sun, curl up on one of the man porches for a lazy afternoon, or wind down the day at the rock fire pit. When the weather cools you can warm up indoors at the pellet stove in the epic great room. You are going to love this cabin escape!

Amazing Lagoon, Beach, Cross Fit Gym, Fishing
This the definition of "Wild and Wonderful West Virginia! magical place, a former rock quarry now lagoon. There is no public access to this property. The only access to the Lagoon, Beach and other amenities is via booking or owners explicit permission. This is a complete unit that is on its own level, own access, own parking, own amenities, Owners live on upper level with fully separate entrance, parking, access, etc. No shared internal spaces. Double sound insulation, no noise worries.

7 Bed/4.5 Bath, Sleeps 14, Sauna, Hot Tub, Pool
Step back in time at this Victorian farmhouse where 1890s charm, elegance, and Art Nouveau décor meet modern comfort. Delight in vintage vignettes, indulge in the chef’s kitchen, and sip coffee on the wraparound porch while taking in the peaceful view. Whether gathering by the fire pit at the barn-inspired hangout, unwinding in the sauna, soaking in the hot tub, or swimming in the seasonal pool, this historic retreat beckons you to relax, slow down, and stay awhile. ⚡️LEVEL 2 EV CHARGER⚡️

Cozy Pool & Hot Tub Retreat by Casino
Welcome to Charles Town, WV! This private pool house boasts two cozy bedrooms and two bathrooms. Perfectly blending relaxation and adventure, our space offers a refreshing outdoor oasis complete with a seasonal pool (available May-September), a premium Cal Spa hot tub open year-round, a convenient gas grill, a smokeless gas firepit, and a charming wood fire pit. Enjoy the many dining options, Hollywood Casino, outdoor adventures, and rich historical exploration right at your fingertips.

Historic Farmhouse w/ Heated Pool, Harpers Ferry
Nestled in the Blue Ridge Mountains, this restored 1800s farmhouse with barn studio is full of character and designed for comfort. The highlight is a heated saltwater plunge pool, open year-round, plus outdoor gathering spaces for summer and three fireplaces for cozy fall and winter stays. Guests rave about the incredibly comfortable beds! The Harpers Ferry area is a delight in every season, offering hiking, history, shopping, dining, river adventures, wineries and breweries.

The Historic Booth House at the Harpers Ferry KOA
The Historic Booth House is great for families for weekend trips or holidays. The house is in a very small neighborhood, located next door the Harpers Ferry KOA Holiday, all of the KOA amenities are included with the your stay (some are seasonal). Each bedroom and bathroom is furnished with linens/towels and basic amenities. Please note this is not a "party" house. No more than 12 people are permitted, day or night. Quiet hours begin at 10pm and are strictly enforced.

Walnut Glen - Quaint 1 Bedroom Country Get-A-Way
Quaint and cozy studio apartment nestled on a quiet country lane just outside of Charles Town. Relax with a glass of wine on the private deck, enjoy a s'more at your personal fire pit or cool off in the built-in swimming pool. Keep an eye out for the deer that come to graze early morning and evening on the 3 acre property. Close to all area attractions without all the crowds. The loft apartment is in a separate building from our home, above my stained glass shop.

Queen Bees Honey Hive
Welcome to our Air Bee and Bee! Full house amenities to include freshly laundered linens each stay! Lots of awesome items not pictured so step inside to see what all the BUZZ is about at Queen Bees Honey Hive! Please note this is a whole house rental! 2100 sq feet. WAIVER OF LIABILITY - Guests agree to release hosts and property from all liability of injuries that may occur regardless of cause or negligence upon booking.
Popular amenities for Jefferson County rentals with a pool
House rentals with a pool

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Condo rentals with a pool

SlopeSide

Rockwell Suite #104 at the Inns of Whitetail

Ski🎿 & hike from front steps—Mountainside getaway

Bear Lodge, Slopeside Condo

Inns of Whitetail #209

Whitetail Resort Ski-in/Ski-out slope side condo.

Rockwell Suite #206 at the Inns of Whitetail

Cozy, renovated Ski & Hiking Getaway - Whitetail
Other holiday rentals with a pool

Queen Bees Honey Hive

The Historic Booth House at the Harpers Ferry KOA

Historic Farmhouse w/ Heated Pool, Harpers Ferry

Walnut Glen - Quaint 1 Bedroom Country Get-A-Way

Riverview Retreat - Pool, Hot Tub, and Mtn Views!

The McCoy House at the Harpers Ferry KOA

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge

Vineyard View Chalet
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- Stone Tower Winery
- Cunningham Falls State Park
- Great Falls Park
- Liberty Mountain Resort
- Whitetail Resort
- Cowans Gap State Park
- Caledonia State Park
- The Links at Gettysburg
- Shenandoah Valley Golf Club
- Berkeley Springs State Park
- Gambrill State Park
- Cacapon Resort State Park
- Creighton Farms
- Robert Trent Jones Golf Club
- Congressional Country Club
- South Mountain State Park
- River Creek Club
- Field of Screams Maryland
- Notaviva Vineyards
- Chevy Chase Club
- Sly Fox Golf Club
- Washington Golf & Country Club
- The Adventure Park at Sandy Spring
- Bowling Green Country Club