Vacation rentals with a pool in Orange County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Orange County

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

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Top guest favorite

A private hot tub is positioned on a wooden deck, inviting relaxation. The exterior of a two-story building is visible in the background, featuring a well-maintained lawn and a staircase leading to a covered porch. Soft lighting illuminates the outdoor seating area.

Apartment in Madison

4.91 out of 5 average rating, 273 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

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A spacious outdoor area features a fire pit surrounded by four Adirondack chairs, arranged on a bed of pebbles. The backdrop displays the multi-level lake house, framed by trees adorned with string lights for evening ambiance.

Home in Locust Grove

4.8 out of 5 average rating, 41 reviews

Hummingbird Lakehouse

Hummingbird Lakehouse in Locus Grove, VA, offers waterfront access to the lake and various outdoor activities like golfing, kayaking, swimming, fishing, and horseback riding. Guests can gather around the fire pit and access community amenities like the pool and beaches. Nearby historic sites & hiking trails provide additional exploration opportunities. If you're looking for a peaceful getaway or an adventure-filled vacation, this lake house offers an idyllic setting for making lasting memories.

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Guest favorite

The charming farmhouse is framed by lush greenery and features a welcoming front porch with white railings. Large windows, adorned with black shutters, allow ample natural light. The entrance is marked by a pair of doors that lead into the home, enhancing its inviting appearance.

Farm stay in Somerset

5.0 out of 5 average rating, 26 reviews

Historic Bloomingdale Farmhouse w/Mountain Views

Situated on the crest of our 14 acre farm with beautiful mountain views on all sides, our 1840's farmhouse is the perfect location for a friends getaway, family retreat or wedding weekend. Conveniently located near several wedding venues including Market at Grelen (5 min), Castle Hill (15 min) and Barboursville (15 min). Plenty of options for hiking, antiquing, sightseeing and eating in all directions: Montpelier; 8 min to Orange; 15 min to Gordonsville; 30 min. to C'ville & Shenandoah Park.

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A serene infinity pool blends seamlessly into the surrounding nature, presenting unobstructed views of the tranquil lake and lush greenery. The calm water reflects soft morning light, while the peaceful ambiance invites relaxation and enjoyment of the natural landscape.

Home in Louisa

4.86 out of 5 average rating, 21 reviews

3 Acre 5BR Resort: private pool, hot tub boat dock

Gather your loved ones at a secluded 5BR lakehouse on 3 lush acres at Lake Anna. Dive into the new heated Salt-Water Infinity pool & hilltop lake view hot tub, soothe muscles in the sauna, or spark friendly rivalries in the game room and volleyball court. Cook up joy in the fully stocked kitchen and unwind by the fire under crystal clear starry skies. Serene water views, fireside chats, and room for every adventure, this is where cherished memories are made—your ultimate private escape awaits!

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A spacious game room is featured, showcasing a large pool table at the center. Arcade games and a home theater setup are arranged in the background. Soft seating provides comfort, illuminated by recessed lighting that enhances the inviting atmosphere.

Home in Orange

4.91 out of 5 average rating, 35 reviews

Near Lake Anna: Gem w/ Saltwater Pool & Arcade!

You may never want to leave this 5-bedroom, 3-bath vacation rental located just a short distance from Lake Anna! Watch a movie on the 110" projector, swim day or night in the heated saltwater pool, and unwind in the 8-person hot tub under the stars. Grill or smoke your favorite meats, then kick back in comfort. If you're looking to venture, visit wineries on the Monticello Wine Trail or head to James Madison's Montpelier for guided tours, gardens, and walking trails. Book your next escape now!

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Guest favorite

The exterior of La Petite Maison showcases a charming guest house with a large screened porch, surrounded by vibrant flower beds. A turquoise umbrella shades a lounge chair next to the seasonal in-ground pool, providing a relaxing outdoor space.

Guesthouse in Gordonsville

4.9 out of 5 average rating, 194 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.

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Guest favorite

A spacious living area is furnished with a light gray sectional sofa complemented by colorful cushions. Three vibrant artwork pieces of ducks are displayed on the wall above, while a wooden coffee table occupies the center. Natural light filters in through the nearby sliding door.

Home in Locust Grove

4.94 out of 5 average rating, 85 reviews

Beach, Hot Tub, Arcade, Golf, Pub: The Lucky Duck!

Unforgettable retreat with partial lake view, luxurious 7-person Jacuzzi, custom pub featuring a retro 4-player arcade with 7,500+ games and trackball, cozy woodstove, and delightful surprises! Ideal for epic family vacations, The Lucky Duck in the exclusive gated Lake of the Woods offers year-round fun—two lakes, eight pristine beaches, two pools, a golf course, an equestrian center, and scenic parks with fitness trails await! Come experience lakeside fun and relaxation! #TheLuckyDuckLOW

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Guest favorite

The historic home, featuring a classic two-story design, showcases a welcoming front porch with decorative railings. An American flag hangs proudly on the façade, surrounded by lush greenery. The driveway leads up to an expansive lawn, offering ample outdoor space.

Home in Gordonsville

5.0 out of 5 average rating, 5 reviews

Experience Luxury, Historic Manor, Private Pool

Enjoy the elegance of a bygone era in a residence designed to sweep you off your feet. Beautifully decorated and updated with modern amenities and rich details, the home is a once-in-a-lifetime experience. Lounge on the front veranda, pour a drink in the pub and stroll down Main Street for Fine Dining, Wine Bistros, and excellent boutique shopping. In historic Gordonsville, you're just minutes from award-winning vineyards, wedding venues, the Blue Ridge Mountains, Woodberry Forest, and UVA.

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Top guest favorite

A serene outdoor area features four white Adirondack chairs arranged around a fire pit on green grass. A private dock extends into the lake in the background, surrounded by trees and calm water, creating a peaceful setting for relaxation.

Home in Locust Grove

5.0 out of 5 average rating, 76 reviews

Lakefront at Turtle Cove

Enjoy the lake life in a peaceful quiet cove on the gorgeous large lake within Lake of the Woods. When not enjoying the newly renovated home with a vaulted ceiling great room, huge screened porch, and a desk and flat screen TV in each room, you can swim, float, kayak, or paddleboard in the quiet, secluded cove, or enjoy the 9 beaches or 2 community pools. Catch fish off the dock in one of the best fishing coves on the lake, and then warm up at night by the fire pit . Great for families.

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Top guest favorite

An aerial view of the historic Woodbourne Estate Manor showcases its striking red roof and white facade. The surrounding landscape features lush greenery, expansive fields, and well-maintained gardens. Pathways are visible leading to the entrance, enhancing the inviting atmosphere of this picturesque estate.

Farm stay in Madison

4.95 out of 5 average rating, 132 reviews

Brewery Manor Sleeps 10 Hot Tub

Woodbourne Estate, circa 1810, is a National and Virginia historic registered landmark Manor House and farm nestled in the foothills of the Blue Ridge Mountains in Madison, Virginia. The 53-acre Estate is also home to our award-winning Bald Top Brewing Company which sits just a comfortable stroll beyond the Manor house. This magical Manor, with its gorgeous grounds, gardens, barns, ruins, pool, stream and vistas awaits! The Manor at Bald Top: Drink in the Moment!

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Guest favorite

A spacious living room features hardwood flooring and large windows offering views of the lake. Comfortable seating includes a light-colored sofa and wooden chairs. A television is positioned near a stone fireplace, enhancing the room's cozy feel.

Home in Locust Grove

4.79 out of 5 average rating, 105 reviews

Lakefront Access | Hour from DC | Kayaks Provided

Welcome to Lakeside Serenity, located in the Locust Grove gated community of Lake of the Woods. This charming residence, situated in a quiet cove, features a spacious backyard with direct lake access perfect for swimming, fishing, kayaking, or lounging lakeside. Enjoy the convenience of an on-site grill for delightful barbecues and dine al fresco in our outdoor seating area overlooking the lake. This home is a haven for anyone looking for a peaceful getaway!

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Guest favorite

Home in Orange

5.0 out of 5 average rating, 16 reviews

Panorama Shores

Take a break and unwind at this peaceful expansive oasis. This lake front retreat boasts more lake access than you can imagine. Your own, pool, tennis court and huge yard to create memories with your friends and family. All linens provided including a set of outdoor towels for your use. The kitchen has been newly expanded and completely upgraded with 3 ovens, 2 islands and 2 sinks. This property was formerly listed as Anna Breeze. Now managed privately.

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