Vacation rentals with a pool in Charlottesville

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Top-rated rentals with a pool in Charlottesville

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

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Guest favourite

Home in Swoope

5 out of 5 average rating, 37 reviews

The Pool House: Hot Tub + Pool + 15 mins downtown

Looking for an extraordinary lodging experience near Staunton, VA but also want the feel-good warmth of a country home? Just 12 minutes from Staunton, this guest pool house features stunning views of the Allegheny Mountains and privacy, but is near all the cultural, culinary, and outdoor recreation amenities of the Shenandoah Valley. The open-concept pool house can accommodate up to 6 guests and features ample outdoor amenities including a shared pool, hot tub, sauna, grill, yard games and more!

Guest favourite

Cottage in Charlottesville

4.86 out of 5 average rating, 78 reviews

Ridgeview Cottage: Mtn Views and Fall Foliage!

This luxury cottage is perfectly situated between Charlottesville and VA wine country on a scenic by-way, offering 4 acres of impressive fall foliage and sweeping mountain views, grill, fire pit, and summer pool access. Located 5 miles from Foxfield and 20 minutes to UVA. Ideal for couples, but can easily accommodate two couples or a small family-- this location offers the best of both; a rural setting with outdoor amenities, yet a short drive to restaurants, shops, breweries, grounds and more.

Guest favourite

Condo in Wintergreen Resort

4.97 out of 5 average rating, 112 reviews

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.

Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

Guest favourite

Guesthouse in Gordonsville

4.91 out of 5 average rating, 180 reviews

La Petite Maison at Hedgeapple Hollow

La Petite Maison (our guest house) is the perfect place to simply get away from the hustle and bustle and relax! Sit in the private screen porch and watch the sun melt into the mountains. Deer, hummingbirds, bluebirds, and the occasional turkey like to hang out on the 8 acres of the property, perfect for any wildlife lover. Enjoy the fenced in common area featuring a seasonal in-ground pool. Conveniently situated near award-winning wineries, Montpelier, and historic downtown Gordonsville.

Guest favourite

Home in McGaheysville

4.99 out of 5 average rating, 147 reviews

KinStay Massanutten Family Cabin - Room to Relax!

Great home in a prime location of the Massanutten Resort close to all the amenities: tubing, skiing/snowboarding, mini golf, GW Natl Forest, and Natl Park! Amazing outdoor activities all around! The home is tastefully furnished and well stocked for enjoying time with family and friends. Enjoy the gorgeous views from the spacious decks, relax in one of the two living rooms watching Netflix on the 65" TVs, or play a fun game of shuffleboard. So many ways to escape in this Massanutten home!

Guest favourite

Guest suite in Ruckersville

4.95 out of 5 average rating, 63 reviews

Cornerstone Farms

Mountain Rustic Elegance describes this clean fully furnished, 1 bedroom apartment in a log home on 80 acres in Greene County with 1 Queen bed, 1 pull out Queen sofa and a rollaway bed (on-demand ),with a fully equipped kitchen,full bath with washer and dryer. Amenities: Dry sauna inside, pool table, foosball table and board games in the closet. Outside: large pool, fire pit, hot tub, Grill. Enjoy eating outside as you soak in the beautiful sunset views while you sit relax and unwind.

Guest favourite

Condo in Wintergreen Resort

4.94 out of 5 average rating, 220 reviews

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

Guest favourite

Home in Robertson

4.92 out of 5 average rating, 206 reviews

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Guest favourite

Home in McGaheysville

4.79 out of 5 average rating, 124 reviews

Paradise Resort at Massanutten

Paradise on the mountain top. A Massanutten, VA location, a country feel with modern style. Located inside Massanutten Village about a mile from the gated entrance into the Massanutten Resort. Sun room with view of the surrounding mountain. Relax as you take in the scenery. Don’t forget a day trip or half day trip on beautiful Skyline drive. Outdoor swimming pool available during the summer. Small family reunions, Corporate work-groups needing extended stays, ALL WELCOMED!!

Guest favourite

Home in McGaheysville

4.91 out of 5 average rating, 138 reviews

Hot Tub~2 Primary Bedrooms~Grill~Walk to Park

Stay with a SuperHost! Retro and cool, The Ski House is a classic A-Frame in Massanutten Resort, Virginia, located inside the gates close to all activities and offering a classic retro mid-century modern decor! But we have not forgotten modern conveniences...internet, hot tub, cable flat screen TV, DVD, dishwasher, washer/dryer, heat and air conditioning, huge hot tub, Weber grill. 4 bdrms 3 baths sleeps 8-9. Our 10 page House Info Sheet details the resort, restaurants, shopping!

Superhost

Home in Ruckersville

4.75 out of 5 average rating, 20 reviews

Kismet Cottage | Cville Home with Pool & Mtn Views

Get-away to breathtaking mountain views in Charlottesville luxury at the Kismet Cottage. Feel away from it all but minutes from it all! Enjoy the whole home featuring 4 bedrooms, with three bathrooms. Relax on the outdoor patio featuring a beautiful outdoor pool, wood charcoal grill on the expansive stone patio and amazing Blue Ridge mountain views. Please note, the owner will stay on site in a separate private suite during your visit should any issues arise during your stay.

Superhost

Home in Rockingham

4.78 out of 5 average rating, 256 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

Heated Salt water pool and hot tub on 2.5 Acres. Lawn games & outdoor living room! New for '21 - Stove, Upstairs Flooring, Foosball Table, Board Games, paint New for '20 - Antimicrobial door handles, kitchen items Completely separate owner/caretakers quarters onsite, occupied by our property manager. Pool, hot-tub, grilling, etc are private spaces for guests and NOT shared *entrance and egress through pool area* *playhouse removed, gas fireplaces inoperable *no pets