Vacation rentals with a pool in Orange County

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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, 153 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

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

4.89 out of 5 average rating, 37 reviews

Blue House and a Pool

Relax at Lake Anna with friends and family at your own pool, hot tub 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.

Top guest favorite

A spacious outdoor pool is surrounded by a well-maintained patio featuring lounge chairs and umbrellas. Lush greenery borders the area, enhancing the peaceful atmosphere. A hot tub sits adjacent to the pool, inviting relaxation in a private setting.

Apartment in Madison

4.91 out of 5 average rating, 254 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*

Guest favorite

A saltwater pool is set within a grassy area, surrounded by mature trees. Seasonal foliage provides shade and a sense of tranquility. The distant landscape features rolling hills, enhancing the outdoor relaxation space which includes patio furniture nearby.

Cabin in Somerset

4.83 out of 5 average rating, 40 reviews

Bloomingdale Honeymoon Cabin w/Mountain/Barn Views

Relax in the rustic cabin retreat set on the hill crest of our 14 acre farm. With mountain views and vintage vibes, it's the perfect getaway for those who want to unplug, or need a change of scenery while working remote! We are near some of the top wineries in VA. There are plenty of options for hiking, antiquing, sightseeing and eating in all directions: 5 min. from the Market at Grelen and Montpelier; minutes to Orange and Gordonsville; 30 min. to Charlottesville & Shenandoah. Come and see!

Superhost

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

4.92 out of 5 average rating, 13 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!

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, 184 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 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.

Home in Locust Grove

4.92 out of 5 average rating, 65 reviews

Beach, Arcade, Hot Tub, 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

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, 97 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

4.92 out of 5 average rating, 24 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, 53 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

The exterior of the property showcases a spacious backyard, featuring a private inground pool with a stone border. Several lounge chairs surround the pool area, enhancing the outdoor relaxation space. A hot tub is positioned nearby, with the house's multiple windows providing a view into the interior.

Home in Mineral

4.9 out of 5 average rating, 70 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.

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, 110 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.