Vacation rentals with a pool in Jefferson County

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Top-rated rentals with a pool in Jefferson County

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

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Top guest favorite

A swimming pool is visible, featuring clear turquoise water and surrounded by a concrete deck. In the background, the two-story residence is partially obscured by lush trees and greenery, providing a natural setting. Poolside chairs are positioned to invite relaxation.

Apartment in Harpers Ferry

4.95 out of 5 average rating, 137 reviews

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.

Top guest favorite

The outdoor area features a spacious saltwater pool surrounded by a stone patio. Several lounge chairs are positioned poolside, and a large grass area is visible in the background. A garden is present along the edge of the patio, enhancing the tranquil setting.

Apartment in Berryville

5 out of 5 average rating, 5 reviews

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*

Top guest favorite

Tiny home in Bluemont

5 out of 5 average rating, 42 reviews

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!

Top guest favorite

Home in Knoxville

5 out of 5 average rating, 88 reviews

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.

Top guest favorite

An aerial view captures the serene blue lagoon surrounded by lush greenery. Two floating platforms rest on the water, while a sandy beach area is visible on the left. Evidence of beach amenities can be seen along the shore, providing space for relaxation and activities.

Villa in Harpers Ferry

4.99 out of 5 average rating, 72 reviews

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.

Guest favorite

An aerial view showcases a spacious outdoor pool surrounded by a concrete patio. Lush green grass borders the area, while a fence encloses the pool for safety. Several lounge chairs are positioned beside the water, providing a relaxing space for guests.

Home in Charles Town

4.97 out of 5 average rating, 32 reviews

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.

Guest favorite

A spacious living room features wooden walls and vaulted ceilings. A stone fireplace is centrally located, flanked by large windows offering views of the outdoors. Two comfortable sofas face a decorative coffee table, with soft lighting provided by a chandelier overhead.

Cabin in Harpers Ferry

4.91 out of 5 average rating, 33 reviews

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!

A cozy living space is created with a dark leather sectional sofa and a matching loveseat, complemented by decorative throw pillows. A patterned area rug lies on the carpeted floor, and a circular shelf displays small items. A chalkboard sign is mounted on the wall.

Apartment in Martinsburg

4.6 out of 5 average rating, 5 reviews

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.

Guest favorite

Home in Harpers Ferry

5 out of 5 average rating, 20 reviews

*NEW* Riverview Rtrt Pool/HotTub/FirePit & View

Welcome to Riverview Retreat in Harpers Ferry, WV! Come and enjoy our 3bd/2ba home with a hot tub and large pool perfectly situated to soak in the 100-mile views over the Shenandoah River! Centrally located within 15 mins from historic Harpers Ferry; within 1/2 mile of public boat access to the Shenandoah River; 2 miles to Appalachian Trail; less than 15mins to numerous breweries & wineries; 10mins to Hollywood Charles Town Casino. Enjoy all this wonderful area has to offer!

A spacious outdoor area features a curved in-ground pool surrounded by a stone patio, bordered by a decorative fence. A two-story farmhouse is visible in the background, framed by lush greenery and clear blue skies, creating an inviting setting for relaxation.

Home in Bluemont

New place to stay

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.

Guest favorite

Home in Harpers Ferry

4.88 out of 5 average rating, 202 reviews

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.

Top guest favorite

A well-maintained saltwater plunge pool is surrounded by a stone patio, featuring six chaise lounges for relaxation. A shaded dining area with an umbrella is positioned next to a rustic wooden structure, providing a serene ambience amidst lush greenery.

Home in Harpers Ferry

4.97 out of 5 average rating, 192 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.