Boutique Hotels in Orange County

Welcome to your lakeside retreat at Lake Anna, Virginia! This spacious home sits on 2 acres and is perfect for families, large gatherings, or a romantic getaway. With 4 bedrooms and 3 bathrooms, it comfortably accommodates up to 11 guests. Enjoy the expansive outdoor space, great for outdoor activities, while the interior is stocked with games and entertainment for all ages. Experience the best of lakeside living!**Sleeping Space:**- Master Suite: King bed with an en-suite bathroom.- Queen Bedrooms: Two queen bedrooms share a conveniently located bathroom.- Bunk Room: 4 twin beds.- Additional Sleeping: A pull-out couch in our basement TV room. The room has doors that enclose it to transform it into a private space for extra sleeping space.**Bedroom Amenities:**- Blackout curtains- Sound machines- Portable fans- Pack and play crib- Baby monitor- Scale**House Amenities:**- Hot tub- Fire Pit- Kayaks- Paddleboards- Life jackets- Pool table- Ping pong- Dart board- Foosball table- Interactive wall games- Fully equipped kitchen- Outdoor grill- Grill utensils- Boat slip for easy lake accessYou will have exclusive access to the entire house, including all the amenities listed above. With the lake just a short walk away, indulge in fishing, boating, and other water activities at your leisure.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

The Farmhouse at Oak Creek Farm is a newly renovated turn of the century farmhouse that is nestled on 85 serene and peaceful acres. Our home is ideal for families and large groups coming to Central Virginia for weddings at Oak Creek Farm or to get away from city life for a bit. Forget your worries in this spacious and serene space.Start your day enjoying the farm life with a breathtaking sunrise while the cows wake up and start grazing across the fields located directly behind the house. Sip coffee on the patio or under the old wellhouse and watch nature wake up from a peaceful slumber. Speaking of slumber, we have four spacious bedrooms, 2 king size beds and 2 queen size beds, where you can drift off without the noise of city life buzzing in your ear. Wake up feeling refreshed and ready to start your day.Having a family get together? The Farmhouse at Oak Creek Farm has a full size volleyball court as well as other outdoor (and indoor) games to keep everyone entertained.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.Please let us know if you need a Pack 'n Play.About customRules:Quiet Hours are from 11:00 pm to 7:00 am.HOUSE RULES: No parties No firearms or illegal drugs (including marijuana) are allowed anywhere on the property No candles,Please TURN OFF the propane tank on the BBQ grill after use. Please do not eat food in the bedrooms Do not move any furniture..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Welcome to Maple Crest and its newest landscaping and garden updates.Whether you are visiting UVA or Woodberry Forest, attending a wedding at The Market at Grelen, enjoying the Montpelier races, or simply spending a few days among wineries and history in the rolling beauty of Virginia’s Piedmont, Maple Crest offers a warm and thoughtfully curated countryside stay in the heart of it all.And yes — pets are welcome. Originally built circa 1929, Maple Crest has been thoroughly renovated while preserving the warmth and character of an early-century Virginia home. The property changes beautifully with the seasons, with flowering trees, mature shrubs, bulbs, and gardens creating color and texture throughout the year.The spacious eat-in kitchen is bright and cheerful, with quartz countertops, new appliances, and generous room for gathering. A sunny breakfast nook overlooking bird feeders is the perfect place to enjoy coffee, catch up on emails, or simply watch the morning unfold just outside the window.The first floor also includes a half bath, a large living room, and a sun-filled sitting room with both eastern and western exposures, ideal for long conversations, afternoon reading, or a quiet evenings as the light changes across the surrounding fields and mountains.Upstairs are three bedrooms, including one en suite bedroom, along with two full baths. The hall bath features an antique clawfoot tub with shower, while the primary bath includes a walk-in shower.A utility basement with washer, dryer, and sink is available for guests' convenience.The house is wonderfully sunny throughout the day, with views of surrounding farms and mountains from nearly every room. Guests often enjoy sunsets from the front porch and sunrises from the back garden with coffee in hand and birdsong in the distance.Mature boxwoods frame the front lawn, creating both privacy and a classic Virginia landscape well suited for croquet, lawn games, or simply relaxing outdoors. Presiding over the property is the magnificent old maple tree that gave Maple Crest its name, a towering presence that transforms with each season and has quietly watched over the house for generations.The fenced backyard offers plenty of room for children and canine companions to run and play, while the acre of fenced pasture beyond provides open space for field sports and seasonal wandering among flowering trees, shrubs, vegetables, and whatever may be blooming at the moment.Maple Crest sits among working farms and quiet countryside roads, where the sounds of chickens, tree frogs, crickets, and the occasional passing train are all part of the historic rhythm and character of rural Virginia life.Despite its peaceful surroundings, Maple Crest is located only minutes from some of Central Virginia’s most treasured destinations, including:The Market at GrelenJames Madison’s MontpelierBarboursville VineyardsCharlottesville wineries and restaurantsscenic hikes and drivesantiques and local farm marketsUVA and Woodberry ForestPlanning a Small Event?We would be delighted to help you host intimate gatherings at Maple Crest, including:rehearsal dinners,bridal luncheons,birthday celebrations,sunset cocktail gatherings,small catered events,and locally inspired chef’s-table dinners.Please inquire ahead to discuss possibilities, availability, and recommendations.We look forward to welcoming you to Maple Crest.About pets:Pets allowed: dogs and cats (limit 2 total).Please, disclose pets UPON BOOKING and note fee..About checkOut:Check out before 12:00 PM.About children:Children allowed: ages 0-17.About customRules:We set thermostat for comfort but modify as needed. Thank you for your reasonable use of the cooling and heating system… Mother nature thanks you too..Thank you for being gentle with furnishings and beddings. We love pets, buy, please do not allow pets on sofas or beds.,At check out, please remove all trash, including from bathrooms, and place in lined bins found inside the “milk house” located in the fenced yard..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 25,Events MUST be approved by host UPON BOOKING..

Welcome to this sprawling 350 acre working angus farm in Somerset VA. This amazing vacation rental offers a fulfilling experience for guests with incredible views and soothing country silence. With 4 bedrooms, 4 baths and plenty of open space, there's room for everyone to unwind. In addition to the Manor House, High Point Farm boasts extravagant and spacious facilities, perfect for weddings, corporate events, and celebrations of all kinds. Our stunning views of the Blue Ridge Mountains, combined with our wide-open spaces, create an unforgettable backdrop for your memorable moments.Located just minutes from James Madison's Montpelier, the fourth President of the United States, our farm is steeped in history. Somerset Virginia is also the birthplace of whiskey legend Elijah Craig, adding to the area's rich heritage. Nearby, you'll find renowned distilleries and wineries, including the nationally ranked Barboursville Vineyards, offering a taste of the region's finest spirits.In addition to its historical significance and scenic beauty, Somerset Virginia offers a plethora of activities for visitors to enjoy. From exploring local distilleries and wineries to attending the famous Montpelier Hunt Races, there's something for everyone to enjoy in our quaint and charming town.Whether you're planning a wedding, corporate retreat, or a weekend getaway, High Point Farm promises to be the perfect destination for your next event. Come and experience the beauty, history, and hospitality of High Point Farm in Somerset Virginia.About pets:No pets allowed, service animals permitted.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:We do not own the property next door which is out the paved driveway gate to the right. They have outside dogs that aren't friendly but are fenced..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Sage Cottage is a beautifully renovated 100+ year old historic house that blends classic charm with modern comfort. Located in the heart of Gordonsville and steps away from restaurants and shops. With room for up to 7 guests, it's a convenient getaway for families and friends. Retreat to the fenced-in backyard for relaxation and games. Explore the Monticello Wine Trail with 30+ wineries nearby. Only 30 min from downtown Charlottesville, indulge in history, shopping, dining, & wine adventures!As you cross our threshold, you'll immediately feel the embrace of history, accompanied by an abundance of charm and intriguing quirks. Our dedication to preserving the past while providing modern comforts has transformed this house into a true gem.Imagine yourself on the covered front porch with a cup of coffee in hand, enveloped in the gentle awakening of the town. Our fully fenced backyard unfolds as a private oasis – a sanctuary where friends and furry companions can relax. Adorned with custom cornhole boards, inviting adirondack chairs, and twinkling string lights, this space beckons you to unwind and savor your vacation.Enter the living room, where the allure of a cozy leather couch and inviting accent chairs invites you to indulge in relaxation. Whether it's watching TV, getting lost in a good book, or engaging in lively board games, this space is thoughtfully designed for enjoyment. Above the couch, a captivating mural showcases the Monticello Wine Trail, complete with a QR code for planning your local winery adventures.Continue down the hallway to the dining room where a spacious table accommodates up to 6 guests, expandable to 8 with the additional leaf. The beautifully renovated kitchen underwent a modern transformation in 2023 and is fully equipped with pots, pans, cooking utensils, an induction cooktop, microwave, Keurig coffee machine, and a cocktail making station. There is also a full bathroom downstairs with a rain shower. Upstairs, discover a tranquil retreat housing 3 bedrooms, each with blackout curtains, plush mattresses, and an array of pillow options from soft to firm. Sleeping arrangements include a total of 5 beds - King Bed, Queen Bed, Twin Trundle Beds, and a Foldable Twin Bed. The bedroom with the queen bed includes an en-suite half bathroom. The second upstairs bathroom boasts modern touches and is generously stocked with amenities such as shampoo, conditioner, lotion, eucalyptus shower spray, and a hairdryer, ensuring your comfort throughout your stay. Upstairs also offers a flex room that can be used as a nursery with blackout curtains and an included travel crib or a peaceful yoga sanctuary. Indulge in the charm of Gordonsville, where history and modern comforts coalesce, creating a remarkable escape that promises restful nights and unforgettable days.About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

Come enjoy this thoughtfully renovated historic home in beautiful central Virginia. Experience an equestrian’s paradise at The Clifton House! Nestled in the foothills of the Blue Ridge Mountains on a 240-acre private horse farm, The Clifton House sleeps up to 11 people across 4 expansive bedrooms in the beautifully renovated historic estate. Our hosts are available to coordinate the ideal equestrian experience you’re seeking — whether you’re planning a family getaway, or you’re an avid rider — we can accommodate all levels! Bring your horse with you, or let us pair you with one of our horses. Our property boasts a large outdoor arena, miles of wooded trails, and spacious boarding stalls. We can assist in scheduling lessons and trail rides during your stay. Spring, summer, fall or winter — we can help plan an unforgettable horse-centric holiday regardless of the season!About pets:Pets allowed: dogs (limit 3 total).Please DON'T feed the horses and keep dogs leashed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.Play pen and high chair provided.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

Your private, spacious farmhouse at Wildwood is less than 2 hours from DC and northern Virginia, less than 6 hours from NYC. 5 bedrooms, 3 and a half baths, on three stories, room for your entire tribe. FAST fiber optic internet with multiple work spaces and views! Skyline Drive, Shenandoah National Park and the Blue Ridge Mountains are close by, for peaceful hikes, relaxing drives, and spectacular sunsets. Staying a week? Pay for 5 nights, 2 are free! Can't fit in everything you want to see, taste and do? Turn a 2 night weekend into 3 with a low-cost Sunday night stay.Wildwood lies at the junction of history and hospitality in the Madison Barbour Historic District, a half-hour drive each to the University of Virginia or Woodberry Forest School. Barboursville Vineyards is ten minutes away. Imagine a spacious, well-equipped kitchen and dining room, plus outdoor deck dining and grill space, to allow you and those you love to relax and celebrate together indoors and out on this working family farm. A guest favorite: the council ring made of ancient stone benches with a firepit for your family to enjoy sunset, fire, moon and stars...all within view of the house. Upstairs in the master suite is a jetted tub for two with a skylight above, with a shower and a private stargazing or sunbathing deck adjacent. New: a play set with a swing for children. Enjoy holidays with family, walking the Big Woods and other trails on James Madison's Montpelier...Monticello...hiking The Shenandoah National Park, Massanutten, Wintergreen. Within easy reach of the Skyline Drive, Old Rag, White Oak Canyon Trail, Shenandoah National Park, Charlottesville, Monticello, Montpelier, vineyards and craft breweries, the Piedmont of central Virginia is your home at Wildwood.Take a short break for a change of work scenery with fast fiber internet.Please note there is no outdoor hot tub and NO pets are allowed in the house or on our working farm. Your events flow gracefully at Wildwood. Please let us know of any event involving more than the folks staying at the farm; separate event fees apply. Wildwood is your perfect base year-round: wineries, Montpelier, Monticello, hikes, graduations, weddings, and most importantly, reunions of friends and family. Here you are secluded, yet close to all the Piedmont has to offer. Follow on IG @farmstayva. Wildwood is your family home for reunions and new unions, new beginnings and old friends.About pets:No pets allowed.About checkOut:Check out before 12:00 PM.About children:Children allowed: ages 0-17.About customRules:Any event or gathering including guests beyond ten overnight guests incurs a taxable event fee for us to manage flows, parking, and event coordination.Open to longer stays. Stays of more than 14 nights/2 weeks incur an additional cleaning fee of $325 every two weeks, scheduled with you, plus deposit,Please mind, this is our housekeeper’s only job she is doing prior to retirement. She supports her whole family with your cleaning fees. Many thanks!!.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.Ask about our Event rental contract and fees!.