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Welcome to Tall Tree Farm

Enjoy quiet, humble luxury: high thread-count sheets, oversized bath towels, firm mattresses and fluffy down comforters. All bedrooms have private en suite bath. Our 60-acre farm features wooded walking trails, a stocked fishing pond, organic garden and a fire pit for an evening with your crew. Take advantage of farm activities or unwind in tranquil peace and quiet – your choice. We are half way between Charlottesville and Richmond, an easy drive to historic places, UVA and scenic wineries.

Entire Farmhouse on 250 Acres Near Charlottesville

Grab your friends, family and classmates and create some memories at Poor Creek Farm. You will stay in a beautifully renovated farmhouse with first-class features and amenities, soul-enriching views, and plenty of space to unwind, relax, and reconnect. Situated on 250 acres of rolling pasture with angus cattle, Poor Creek Farm is 30 minutes from Charlottesville, UVA, Monticello, and wineries. Plenty of space with 5 bedrooms, four baths and spacious common areas to spend time with friends.

Pleasant View Farm Guest House

Pleasant View Farm is a working Angus cattle farm located in the heart of the Green Springs National Historic District. Views of the Blue Ridge Mountains and beautiful pastures are seen from all aspects of the house. Located close to I 64 and a short drive to Charlottesville and UVA, Richmond, wedding venues, Gordonsville, Orange, Monticello and Montpelier. The area is abundant in wineries and brewerys. Tear drop driveway is perfect for parking your boat trailer while visiting Lake Anna.

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.

Homestead Haven of Keswick

Step into our farms original 1930s homestead & experience a blend of historic charm and modern comfort. Nestled among lush greenery, veteran oak trees, and beautiful crepe myrtle trees. Relax in the spacious, fenced-in backyard under wide open skies, complete with a classic tire swing that brings back the joy of simpler times. Homestead Haven offers plenty of room to roam, inside & out. Sip your morning coffee on the cozy front porch, explore Cville, or unwind in the peaceful atmosphere.

Authentic 3 Bedroom Log Cabin, with Lake Access

Knotty Pines is the perfect place to make some memories at this unique and log cabin at Lake Anna. It is exactly the escape you need to leave all your stress behind offering you everything you need for vacation bliss. It features a perfect medley of rustic natural stylings and modern upgrades that will make you feel right at home. Pull in the driveway and let the experience begin! Take in the sight of tall trees as you head up to the covered porch with the woods singing a sweet symphony.

Pinecrest House

Located just off I-64 and Route 250, Pinecrest House is ideal for guests visiting Charlottesville & Richmond who prefer a quiet retreat. It’s especially convenient for holidays, vineyard tours, family visits, and stays where multiple destinations are involved. With Firefly high-speed fiber internet, a large open kitchen and great room, and thoughtfully furnished bedrooms, it’s ideal for guests who want space, comfort, and quiet. Sleeps up to 6 adults comfortably (4 bedrooms + 1 couch).

Chicory Cottage

Cozy 3BR, 2BA cottage in rural Virginia—perfect for peaceful getaway. Each bedroom has a king bed, plus daybed and pullout sofa for up to 7 guests. Enjoy a fully equipped kitchen, high-speed Wi-Fi, smart TV, washer/dryer, and a dedicated workspace. Guests have full private use of the cottage and outdoor areas. Owners live on-site in a separate home and respect your privacy. Close to Rt 64, Richmond, Charlottesville, trails, wineries, and other Central VA attractions.

Dog-Friendly Lake Home w/ Large Fenced Yard

Bring the whole family- including the pups- and enjoy all Lake Anna has to offer! This home has everything you need for relaxing stay with water access. Inside there are enough rooms for the family, and outside you can spend time in nature while your dogs run around in the large fully fenced yard. Just across the street you can drop the kayaks in the water or just enjoy the view from the front porch with your coffee or glass of wine! Welcome to Dog Days House

Quiet Cove at Lake Anna

Waterfront at it's finest on Lake Anna located on the public/cold central side of the lake, in a quiet cove. Our home is fully furnished with a modern vibe. The kitchen is equipped with all the appliances and necessities you need to enjoy your stay. We have a great dock that you can lounge and hang out on as well as dock your boat or jet ski's. Property is equipped with a Ring camera doorbell located at the front door. Owner is a licensed active VA Realtor.

Not Your Average Lake House - 4 BR 15 guests

Get away to a unique, modern waterfront retreat on Lake Anna’s public side! With a private dock & spacious 4800 SF this vacation home has towering ceilings that are as high as 3 stories and no less than 10 ft, true floor-to-ceiling windows with vast water views, and cozy furnishings—perfect for summer fun vacation, spring break, or a working stay-cation. Hot tub, fire pit, kayaks, paddle boards, billiards, shuffle board, free EV charger, & pet friendly.

NEW Lakefront Lake Anna, Beach, Dock, Hot Tub

Welcome to House of Memories, a brand-new 5BR, 5.5BA lakefront retreat on the quiet Private Side of Lake Anna, built for big groups and family fun. The walkout lower level is its own entertainment floor: movie theater, arcade games, shuffleboard, foosball, and a kids' playroom. Outside, a hot tub, a private dock with covered boathouse, lakeside fire pit, screened porch, and a covered patio with grill. Sleeps up to 20. Built for memories.