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Farm Stay: Vineyard, Animals, Heated Pool

Welcome to Orchid Hollow, our family farm and vineyard in the Virginia Piedmont. The carriage house awaits at the end of winding country roads and a long gravel drive. Start your day with coffee on the deck overlooking the vineyard as horses graze below. Spend the afternoon by the heated pool, or grab a fishing pole and head to our 5-acre lake for fishing, canoeing, or a pedal boat. End the day with wine by the lakeside bonfire as the sun sets and kids run free or swim in the color-lit pool.

Lakefront | Pool, Hot Tub, Dock, Foosball, Peloton

Lakefront retreat on 2.7 wooded acres, stunning lake views, resort-style amenities perfect for family getaways. • Private POOL & HOT TUB overlooking lake • Dock: Adirondack chairs, paddleboards, water mat & fishing rods • Deck: Gas grill, fire pit & outdoor dining • 1/4-mile hiking trail through woods • Gym: Peloton & weights • Gameroom: pool table, foosball & darts • EV Charger • Lawn space for cornhole & outdoor fun • Expansive deck w/ peaceful view & wooded surroundings • Happy dog fee $179

Lakefront Lake Anna, Fire Pit, Pool, Beach

Waters Retreat is a fully equipped, lakefront home on the Private Side of Lake Anna—just bring your clothes, swimsuits, and water shoes. Nestled in a quiet cove at the end of a cul-de-sac, this peaceful retreat features 160 feet of shoreline, a private boat dock, private beach, kayaks, fire pit, hammock, deck, and a game-filled basement. Located in The Waters with access to a pool, tennis, pickleball, beach, playground, and marina. Perfect for family fun, lake adventures, and relaxing in style.

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.

Discounted Holiday Getaway Perfect For Families

Welcome to Always On Lake Time! We are your destination for relaxation and unforgettable family fun at Lake Anna. Our retreat offers access to the lake from the comforts of The Waters at Lake Anna, a private, resort-like community. Enjoy mornings sipping coffee on the front porch, afternoons by the community pool and beach, and evenings playing tennis. Fish from the community docks or launch your boat. We also have a game room, two kayaks, two paddle boards, and life vests for your enjoyment.

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

4 unique rentals available (click our profile)! Unwind at this Central VA Country Paradise! Stay in a converted Barn & Silo w/ private natural swim pond and waterfall tucked into the woods on 140 Acres! Your own Oasis awaits, step out on your porch for coffee/drinks with the farm animals. Take a hike around the Lake on the 5+ miles of trails before cooling off in the pond while you gaze up at the stars. Sheep, Dwarf Fainting goats(next to silo 10' away), Chickens, Ducks, Bunnies, & Turkeys.

Venson’s Getaway!

Venson’s Getaway is a beautiful house that was recently remodeled into a comfortable and cozy getaway. The house sits on 30 acres of peaceful and private land, and in its immediate surroundings it has a nice patio with a fire pit and three grills, and a beautiful heated swimming pool that was also recently finished. The area is surrounded by nature, including a creek that runs through the property! It is also located 30 minutes away from Charlottesville (famous Monticello's location!)

Nature’s Nook at Lake Anna

Welcome to your perfect Lake Anna family retreat! This spacious home sleeps 10 across 5 cozy bedrooms and 4 bathrooms, offering plenty of room for everyone. Enjoy the private boat dock for lake adventures, relax in a cozy backyard, or take a short walk to the beach. The dedicated workspace is ideal for remote work, while the large deck and backyard are perfect for outdoor activities. This home is ideal for boating, swimming, and unwinding in a peaceful, family-friendly getaway

Shenandoah 2BR Yurt on delightful Resort w/amen.

Located on over 1,000 acres of rolling hillside that encompass a scenic 60-acre lake, Shenandoah Crossing® is the perfect place to stay for those who love the outdoors. The resort combines an old country estate and horse farm with acres of wilderness in a pristine area. Try our 2-BR luxury yurt stay which includes four-poster beds w/plush linens, flat-screen TVs, elegant bathrooms and fully-equipped kitchens, all with central heat and air, large deck area w/ summer kitchen.

Shenandoah 2BR Cabin, Scenic Resort w/ Amenities

Relax on this expansive 1,000 acre rolling hillside resort encompassing a scenic 60-acre lake with breathtaking views. Enjoy the extensive, family friendly amenities or stay cozy inside your private rustic cabin. The resort combines an old country estate & horse farm with acres of wilderness in a pristine area that lies just beyond the Shenandoah Valley. *Before booking, click below to review “The space” and “Other details to note” for important information.*

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.

Lakefront Escape | Private Pool + Dock Access

Immerse yourself in lakeside luxury at our serene waterfront retreat, located in the premier Rock Island Landing community on the private side of Lake Anna. Built in 2024, this spacious home features an open-concept design with three separate living areas, perfect for families and groups. Enjoy exclusive amenities, including a private boat dock, hot tub, fire pit, and a brand-new private waterfront pool for the ultimate lake getaway.