Vacation rentals with a pool in Orange County

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.

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.

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.

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!

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.

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.

Hot Tub, Arcade, Golf, Pub, Beach: 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

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.

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.

Sauna & Game Room: Lake House in Locust Grove!

Spa Room | Community Amenities (Paid + Complimentary) Experience lake livin' at this welcoming Locust Grove vacation rental! The 2-bedroom, 2-bath home is ideal for groups yearning for recreation and relaxation. Explore the area's historic sites, then return home to let your worries melt away in the infrared sauna and steam shower, unwind by the wood-burning stove, or enjoy a game night in the rec room. Stay on-site and enjoy optional access to community pools, a playground, and more!

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.

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!