Holiday rentals with breakfast in Orange County

Groom's Cottage - The Inn and Tavern at Meander

A charming, private cottage near the stables, Washington Cottage and Madison Cottage. Enjoy spectacular mountain views and breathtaking sunsets steps away from the main house at our romantic Virginia inn. The Groom's Cottage, which originally housed the groomsmen caring for the horses, features a king size bed with elegant linens, newly refinished heart pine floors and newly renovated private bath with tub and spa shower. A gas fireplace completes the ambiance of the room. The Groom's Cottage is pet friendly with in-room Wi-Fi.

Lake Life with all the Views!

Unwind at this tranquil Lake Anna retreat! This 5-bed, 3-bath home welcomes you with stunning sunrises & breathtaking sunsets from your screened-in porch, deck, or dock. The open-concept main level living features panoramic water views in the the cozy living room, sitting area, spacious kitchen with bar & dining area for 10. The lower level offers 2 bedrooms, bath, family room & more. With a game room & dock for boating, fishing or sunbathing, this serene lakeside getaway is your perfect escape!

Romantic & Private Guest Cottage on a Lovely Farm

Nested at the base of Cedar Mountain, the 100 acre Farm at Cedar Mountain's guest cottage is a beautiful mix of mid-century modern and vintage. It's the ideal space for a couple looking for a romantic getaway or for friends wanting to explore the area and relax. Please contact us in advance if you are interested in bringing a pet. PRIOR APPROVAL is required and a pet fee per dog (up to 2) is required. No unattended pets are allowed in the cottage. Please do not allow them on furniture.

Lynn Haven Manor

Stately Virginia manor home, private landscaped grounds, 60 miles to DC and 55 miles to Richmond. Visit numerous nearby historic sites, such as Montpelier and Monticello. Also nearby are many of Virginia's most celebrated wineries, Barboursville, Keswick, Merrie Mills and many more, not to mention our fabulous fox hunting country. Enjoy the comfortable bedrooms, plenty of private spaces to relax, read or just reflect. Everything you want to explore is right outside the door of this place.

Farm Cottage just outside town of Orange.

Charming 1920's cottage on a large farm just outside the town of Orange. Completely renovated and updated. Convenient to vineyards, battlefields, wedding venues and popular tourist destinations. Bucolic setting, very private. Spaces to enjoy the out of doors. Less than 2 miles to in-town wedding venues and Rounton Farm. Less than 4 miles to Inn at Willow Grove. 5 miles to Montpelier. Less than 7 miles to Grelen. 10 miles to Gordonsville. 12 miles to Barboursville. 19 miles to Mineral.

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

Renovated duplex in Madison, VA. Enjoy a peaceful setting, amazing views and convenient to wineries, wedding venues & hiking. SAUNA! On-site walking trail. Near Early Mtn Vineyards, Prince Michelle Winery, Yoder's Market, Bald Top Brewing & Plow & Hearth. A 30 min drive to Charlottesville, Shenandoah Nat. Park, Culpeper & Orange. Shopping, restaurants, breweries, antiquing, site seeing and more. *RENT ENTIRE HOME* - Inquire for our unit A & B combined rate. Dogs allowed-$30 fee.

Lynn Haven Manor - Hunter's Retreat

Stately Virginia manor home, private landscaped grounds, 60 miles to DC and 55 miles to Richmond. Visit numerous nearby historic sites, such as Montpelier and Monticello. Also nearby are many of Virginia's most celebrated wineries such as Barboursville, Keswick and Merrie Mills, not to mention our fabulous fox hunting country. Enjoy our comfortable bedrooms, and the plenty of private spaces to relax, read or just reflect.

Private guesthouse with full bath and free parking

Take it easy at this unique and tranquil getaway. Brand new private room, detached from original farmhouse. Private entrance behind garage. Centrally located to many nearby vineyards and breweries, and 25 minutes from Charlottesville. If you are looking for a getaway, you will find rest and relaxation here. Enjoy the abundance of several vineyards and breweries close by, as well as hiking. Come visit Barboursville.

Women's Weekend Wellness Retreat

Welcome to a transformative weekend healing retreat designed exclusively for women—a safe, nurturing space where you can relax your nervous system and reconnect with your inner peace. Over the course of this retreat, you’ll experience a unique blend of restorative activities, including playful goat therapy, therapeutic crafts, and empowering affirmations to help renew your soul.