Holiday rentals with a pool in Jefferson County

Berryville Bliss

Enjoy your private escape in historic Berryville, VA. Walking distance to Rosemont Manor, restaurants, parks, pickleball courts, and short drive to the Appalachian Trail, breweries, and wineries. Our newly renovated basement apartment offers 2 spacious bedrooms, 1 luxurious bathroom with large shower and Jacuzzi tub, full kitchen, and cozy living room, all with private entrance. Unwind in our saltwater pool and hot tub after exploring the town. *Heated pool and hot tub available May 2-October*

The Coop

Welcome to The Coop! Nestled in a wooded mountain community, this rustic hen house has been lovingly transformed to offer a unique off-the-grid experience. Within 2 miles of both the Appalachian Trail & wineries, The Coop blends rural charm with modern comforts through solar-powered amenities, fresh linens, telescope stargazing & a secluded fire pit. While there haven't been hens at The Coop in decades, guests are welcome to enjoy their fresh eggs & visit them living happily across the street!

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.

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.

Mountaintop Cabin w/ Poolside Sunsets!

MOUNTAIN MAMA VACATION HOMES 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!

Safe upscale unit w/ parking

Spacious (1100 sf) apartment. The living room has high end furnishings. kitchenette . Private bathroom, office area, bedroom:queen bed, reading nook with relaxing swing chair and armoire The dinning area has a bar for your enjoyment. 55” smart tv fast internet/WiFi. Netflix, Amazon Prime, and Hulu are included . New, upscale neighborhood with walking trails, swimming pool and tennis courts. Shared deck/back yard with a gas grill and seating for four. Shared high end washer/dryer.

Beautiful Farmhouse

Beautiful farmhouse nestled on 6 acres of wooded property overlooking the Shenandoah Valley. 6 bedrooms, 6 full baths and 2 half baths make this the perfect getaway. Main level boasts newly renovated gourmet kitchen, 2 stone hearth fireplaces with electrical inserts, living room and game room. 3rd Floor has separate entrance and full kitchen. Outdoor in ground pool and detached 2 car garage. Side parking area for additional guests and large flat back yard great gatherings.

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.

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.