Vacation rentals in Wilderness

Iconic Farmhouse w/ Furnished Silo & Highland Cows

This beautiful house is the culmination of eight friends’ vision for an ecological and architectural experience. Set on a picturesque 33-acre grassfed cattle farm, this 4 bedroom, 3 loft, 2.5 bath dwelling is ideal for family get-togethers and intimate reunions with old friends. Many Blue Ridge Mountain sunsets have been celebrated from the open air balcony. Due to the number of staircases and separated rooms, the property is not ideal for folks with toddlers or those with mobility limitations.

The Garden View Suite—Zero In Hidden Fees!

Private luxury. This serene guest suite is situated on a 43-acre farm--Bees & Trees--and is attached to the North end of the main farmhouse. A private garden-gate takes you straight to your suite just steps from the pool. Enjoy a magical sky full of stars while relaxing in the hot tub or enjoying the fireplace! There are breathtaking sunrise views from your front windows, gorgeous sunsets from your back porch and the nearby gazebo gives you both views. You owe yourself a stay with us!

Timber Creek: Falls - A Shenandoah Cabin

Nestled on 8 acres, the Timber Creek Falls A-frame sits on the Shenandoah National Park border overlooking a beautiful cascading waterfall. A 90-min drive from DC, this cabin getaway will have you unwinding in tranquility. A hot tub offers views stretching 50mi to West Virginia on a clear day, and the closest neighbor is a half mile away. A truly private retreat comes w/ modern conveniences including: EV charger, smart devices, flat-screen TV, standing desk, wood burning stove & spa bathrobes.

Lakefront Retreat | Hot Tub • EV Charger • Gazebo

⭐ ABOUT THIS SPACE ⭐ Escape to your own private lakefront retreat on Wilderness Run Lake. Wake up to peaceful water views, spend your day kayaking or fishing right from the dock, and unwind in the hot tub surrounded by trees as the sun sets. 🌿 WHAT MAKES THIS PLACE SPECIAL 🌊 Direct lake access with private dock and kayaks 🛁 Secluded hot tub 🌳 Gazebo for enjoying nature and flat top grill for breakfast 🔥 Outdoor chimney by the lake 🔌 EV charger on-site (perfect for Tesla & EV travelers)

Beach, Hot Tub, Arcade, 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

Cozy Farm Apt near Cville•wineries, mt. views

Come experience a relaxing getaway on our family’s dairy farm! Set in beautiful Orange County, We are close enough to Charlottesville (25 min) to fulfill all your shopping and eating needs, but have the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

Our Happy Place #LuxuryLogCabin HOT TUB Waffle Bar

This is seriously our happy place :) Enter this luxury log cabin and in an instant, experience breaths of happiness, gratitude, and connection. This is a place where you come to REFUEL & CONNECT with your loved ones and friends. Our Happy Place features 5 uniquely designed bedrooms with potential to sleep 14, 3.5 bathrooms, & aesthetic originality all throughout. The house features a Hot Tub, Fire pit, porch swings & a WAFFLE BAR. Say what? Its the ultimate place for relaxation!

Cozy Farmhouse Getaway

Life is good on the farm! Our charming three-bedroom guest house offers a true home-away-from-home experience, where rolling fields, open skies, and friendly cows are your closest neighbors. Enjoy breathtaking sunrises and sunsets in a peaceful countryside setting, just 11 miles from downtown Culpeper. You’ll be close to numerous wineries, breweries, and historic sites, with easy day trips to the Shenandoah Mountains, Lake Anna, Fredericksburg, Charlottesville, and Washington, DC.

Stanley’s Cabin- Beautiful farm with private pond

Located at the foothills of the Blue Ridge Mountains in rural Culpeper County, Stanley’s Cabin sits on a private 7 acre pond surrounded by trees, open land, and grazing cattle. Ideal for couples, families, or small groups! Play a game of corn hole, fish for large mouth bass, take the kayak or canoe on the water, or just enjoy a peaceful walk. Many tourist attractions and activities are within proximity. Stanley’s Cabin awaits your next adventure or trip for rest and relaxation!

Hidden Haven

Hidden Haven is just that! A 600 square foot romantic, private, peaceful, little haven. Hidden in the woods just 6 miles outside of the Town of Orange. Open the garage door in the living area and step out on the 300 square foot screened in porch where you can relax at the firepit under the covered roof. On the porch at Hidden Haven, we like to say, "time wasted is time well spent". The romantic vibe and modern amenities make it a prefect place for a couple's getaway.

Romantic A-Frame for 2 w/ Hot Tub + Fire Pit

Escape to your own private A-frame retreat—designed for couples seeking romance, relaxation, and unforgettable time together. This cozy getaway blends nature, privacy, and comfort in one unforgettable setting. Spend your evenings soaking in the private hot tub under the stars, gather by the fire pit. Whether you’re celebrating an anniversary, planning a surprise getaway, or simply craving time away together, Escape was created for meaningful moments.

The Carriage House at King's Crossing

The Carriage House at Kings Crossing is a recently renovated and tastefully furnished three bedroom/two bathroom home. Its unique charm captures a contemporary rural feel, next to the heart of historic Fredericksburg! King's Crossing is nestled between downtown Fredericksburg and the battlefields; you will find that getting to local attractions is an easy drive. Additionally, we are within 1 hour of DC, Richmond, and Shenandoah.