Holiday 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.

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)

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!

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. An inviting front porch with swing is waiting for you @walnuthillcabin

Beachwalk Hideaway

Escape to our delightful Beachwalk Hideaway, a cozy retreat that offers easy access to the serene beach on the shimmering lake. Walk just 6 houses down to Ramsey Beach for sandy shores on the lake. Lounge by Ramsey Beach water's edge, build sandcastles, swim, and immerse yourself in the calm of lakeside living. As evening falls, enjoy breathtaking sunsets and starlit skies from your piece of paradise. Book your stay now and experience the ultimate in lakeside relaxation and recreation.

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!

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.

Life on the Lake, enjoy the peace and kayaks

Located within 20 minutes of both Fredericksburg and Culpeper, Virginia, this 2000 square foot home offers lakefront living on the 24-acre Keaton’s Lake within the gated community of Lake of the Woods. Keaton’s lake is ideal for fishing, swimming, kayaking or just lounging on the hammock or by the firepit enjoying the peaceful setting and beautiful view. Guests can also enjoy the 500 acre Main Lake and its beaches and parks.

Mountain Cabin Getaway w/WiFi, TV, Fire Pit, Patio

This unique, modern cabin is located only minutes from Old Rag Mountain, White Oak Canyon, trout fishing, horseback riding, wineries, breweries, and more! This 400 sq ft. tiny home has all the modern amenities you need to feel right at home. Step outside and relax on your private patio with a cozy fire and s’mores. Are your desired dates already booked? Check out our other listing, Black Bear Cabin!