Family-friendly holiday rentals in Louisa County

Pullman Train Car at Rassawek

Our Pullman Car is one of 3 converted train cars available for rentals. The car was built by Pullman Co. in 1888. Guests staying in this car have access to the shared amenities of Rassawek Station including the patio “Flat Car” and our Lodge Cabin. Guests can also use the ponds on the property as well as the 5+ miles of private country roads for hiking, running and biking. The converted car has a living area, full kitchen, a bedroom with two double beds, a full bath with shower and a half bath.

Farm Stay: Vineyard, Animals & Room to Roam

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.

Welcome to Tall Tree Farm

Spend a weekend or more at this unique and tranquil farm getaway. Unwind in the country with walking trails, swimming, fishing in our stocked pond or enjoy an evening around a bonfire with your family and friends. Tall Tree Farm is our home and we invite you to come find out what makes this place so special. Only 45 minutes to Richmond, 25 minutes to Charlottesville and The University of Virginia, 33 minutes to Thomas Jefferson's Monticello and minutes from wineries, breweries and distilleries.

Wellness Cabin W/ Hot tub, Sauna, Cold Plunge.

Soak in the cedar wood burning hot tub/cold plunge. Unwind in your private Sauna. Relax by a firepit with a pizza oven (dough, cheese, sauce, pepperoni supplied). Find some peace along the natural spring in the mediation/breathwork area. Hike/Bike on the trails. Put your feet up for a lovely outdoor projector movie night. River Bend Retreat is a self-guided wellness retreat that allows 2 guests to destress, reconnect to nature, and truly experience deep rejuvenation of mind, body, and spirit.

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.

Tugboat/Private Lake - Farm Animals - Fish, Swim,

Get swept away to a Magical Tug/Houseboat! Newly renovated with all modern conveniences, incl. fully stocked kitchen, full bathroom, AC, heat, & WiFi. Tug floats on an 8 acre private Lake w/ Island on 142 Wooded Acres, with 5+miles of hiking/biking trails. Enjoy Swimming, Kayaking, SUP, Fishing, Hiking, Biking, Exploring, or just relax on your own beach by the fire pit. Visit farm animals just a short walk around the lake...Theo the Cow, Sheep, goats, turkey, ducks, chickens, and rabbits.

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.

Huge 8BR Lakefront Lake Anna, Beach, Dock, Hot Tub

A World Away is a private luxury lakefront retreat on Lake Anna’s public side, set on 3.5 acres with 600 feet of shoreline and sweeping views. This ~7,567 sq ft estate features 8 bedrooms (5 suites), ideal for executive retreats, large gatherings, and multi-family stays. Enjoy a deck, hot tub, firepit, sandy beach, and a full game room with theater, pool table, ping pong, and foosball, plus direct access to boating, swimming, and fishing—offering rare privacy and a true D.C. escape.

Wine Country Cottage, Hot Tub, Game Room, Slps 12

Connect with family at this cozy cottage, nestled in the historic town of Gordonsville at the heart of Virginia's wine country. Gather all the family under one roof during your stay while taking excursions to award winning wineries, breweries, and attractions in and around Gordonsville or nearby in Charlottesville. When you're staying at the cottage, you'll find plenty to do with the game room, pool table, deck w hot tub, large fenced backyard, toys for kids, and more.

New Luxe Lake Anna Lakefront-5BR Suites-Dock-Beach

Welcome to Built for Memories — a newly constructed luxury lakefront estate on the Private Side of Lake Anna, designed for elevated living and unforgettable stays. Set on a private stretch of shoreline with sweeping water views from every room, this home blends high-end materials, refined design, and seamless indoor-outdoor living. Every detail from the views to the finishes has been thoughtfully curated to deliver a truly premium lakefront experience.

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.

Secluded Cabin•HotTub•Fire Pit•Porch•Water Access

Welcome to your cozy log cabin escape near Lake Anna; perfect for families, couples, friends, or a laid-back getaway with your favorite people. Start your mornings on the screened porch, spend the day on the lake, then unwind in the hot tub or by the fire under the stars. Highlights: ✅ Hot Tub ✅ Fire Place/Pit ✅ Fully equipped kitchen ✅ Peaceful ✅ Relaxing ✅ Quiet ✅ Kayak ⚖️ Honestly, check out the reviews!