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 spacious dining area features a large wooden table set for six, surrounded by stylish chairs. Natural light floods the room through multiple windows, accentuating the neutral décor. A chandelier hangs above, complemented by wall decor that showcases the cozy ambiance.

Cottage in Locust Grove

4.99 out of 5 average rating, 136 reviews

Quaint & Cozy LakeView Cottage - Lake of the Woods

Welcome to Brent and Carla's Lake View Cottage! Our beautifully renovated, fully furnished, unique and luxurious home is stocked with everything you need to enjoy your stay in beautiful Lake of the Woods. Our cozy cottage is a perfect get-away for your next vacation, visit with family, work trip, staycation or weekend getaway. You will instantly be set at ease as you enter our home featuring wonderful décor, detailed craftsmanship and lots of amenities to make your stay relaxing and memorable.

Guest favorite

A saltwater pool, surrounded by a manicured lawn, reflects the clear blue sky. Leafless trees and lush greenery provide a scenic backdrop, with a farmhouse visible in the distance, enhancing the tranquil outdoor setting.

Farm stay in Somerset

5 out of 5 average rating, 16 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.

Guest favorite

A seasonal in-ground pool is surrounded by a concrete deck, reflecting the nearby guest house and verdant landscaping. The fenced yard features a lawn with various plants, and the screen porch is visible on the house, providing a serene outdoor space.

Guesthouse in Gordonsville

4.91 out of 5 average rating, 182 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.

Top guest favorite

A private in-ground pool is surrounded by a spacious concrete deck. Adjacent seating includes white lounge chairs. A water slide is positioned at one end, and the area is framed by lush trees in the background, reflecting a serene outdoor setting.

Home in Aroda

4.98 out of 5 average rating, 86 reviews

Sunset Retreat a cabin off the beaten path

Relaxation and quiet are two words that come to mind at Sunset Retreat. Close enough to stores for convenience but far enough away for solitude. Large yard, fire pit and concrete area if children want to create a masterpiece in chalk, there is also a tree swing next to woods. Close to many wineries, breweries and hiking. No WIFI or satellite tv, we have antenna only. You are welcome to bring your own hotspot . We have one smart tv. There is also a private in ground pool for summer time use.

Guest favorite

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

4.89 out of 5 average rating, 19 reviews

Hummingbird Lakehouse

Hummingbird Lakehouse in Locus Grove, VA, offers stunning waterfront views 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.

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 out of 5 average rating, 45 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.

Guest favorite

An aerial view of a blue house showcases a spacious pool area with sun loungers and umbrellas. The landscape features a manicured lawn and nearby trees, providing a serene setting. The wrap-around porch can be seen, emphasizing the inviting outdoor spaces.

Home in Mineral

4.85 out of 5 average rating, 27 reviews

Blue House and a Pool

Relax at Lake Anna with friends and family at your own pool and dock. Blue house boasts numerous spaces for entertaining and private chill time. House features 4 bedrooms, 3 large couches and 3 full bathrooms. The gourmet kitchen is fully stocked and ready for a home cooked meal after a full day on the lake. Tim's at Lake Anna is a short car ride or boat ride to enjoy a meal and cocktail. The Cove and Lake Anna Plaza at the 208 bridge are close by including boat and jet ski rentals.

Guest favorite

A spacious outdoor area features a sparkling saltwater pool surrounded by lounge chairs. The adjacent home showcases large windows and a raised patio, providing access to multiple seating options. A basketball hoop stands nearby, enhancing opportunities for outdoor recreation.

Home in Mineral

4.95 out of 5 average rating, 56 reviews

Secluded Lakefront | Private Pool | Dock | Hot Tub

**Discover Ultimate Luxury at LesLee at the Lake: a Deep Water Lakefront Haven with Private Inground Pool, Hot Tub, and Dock** Nestled on the public side of Lake Anna, this picturesque 2.63-acre secluded property offers stunning waterfront views, a boat house for easy water access, and a lakefront fire pit. Our expansive and luxurious 9,000 sq. ft. home with game room, spacious kitchen, and movie theater, is ideal for an unforgettable escape and perfect for accommodating large groups.

Guest favorite

A bright blue water slide curves into the clear swimming pool, complemented by a sunny pool deck. Steps lead up to a raised platform, while a diving board is positioned by the edge of the pool, inviting guests to enjoy aquatic activities.

Cabin in Locust Grove

4.96 out of 5 average rating, 50 reviews

Jacuzzi/Beaches/Golf/Pub/Arcade: The Lucky Duck!

Unforgettable retreat with stunning partial lake view, luxurious 7-person Jacuzzi, custom pub featuring a retro 4-player arcade with 7,500+ games, 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

A clear, blue swimming pool is visible from above, surrounded by a white fence. The pool features a concrete deck and is designed for relaxation during warm weather. Sunlight reflects off the water's surface, creating a serene atmosphere.

Guest suite in Gordonsville

4.88 out of 5 average rating, 109 reviews

2 Bdrm Private Suite @ Sunshine Acres

Charming guest suite in our home located in the Central Virginia countryside on 18 partially wooded acres. We offer early check in and late checkout, perfect for wedding guests & overnight trips. Relax to the sights and sounds of nature while exploring the area's many historic landmarks and award winning wineries. Due to the nature of our work as an active sanctuary for senior dogs, our space is not suitable for children under 15. We are able to accommodate infants upon request.

Farm stay in Madison

4.96 out of 5 average rating, 109 reviews

Brewery Manor Sleeps 10 Heated Pool 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!

Top guest favorite

An aerial view of a serene 5-acre farm is captured, surrounded by lush greenery. A cozy structure is situated amidst the trees, with a gathering area nearby. The expansive landscape offers an inviting atmosphere for exploration and outdoor activities.

Farm stay in Barboursville

4.98 out of 5 average rating, 215 reviews

Moonfire Farm cozy Shenandoah Region Getaway

Experience charm and nature at Moonfire Farm! Our finished basement on a 5-acre hobby farm offers delightful animal encounters with chickens, ducks, alpacas, and hilarious goats. Our active family of three, including our 7-year-old daughter Piper, welcomes you. High-speed Internet and nearby wineries, breweries, hiking trails, and pick-your-own fruit locations await you. Explore our guidebook for recommendations. Book now for a memorable farm getaway!