Virginia is home to more than 200 wineries in its northern and central regions, and this year local winemakers need support more than ever. Severe frost hit vineyards across the state this spring, damaging vines and leading to a challenging harvest season. October is Virginia Wine Month, and wineries, restaurants and hotels are marking the season with special opportunities to explore the Commonwealth’s countryside. Why not plan a harvest overnight of your own? Book a stay at one of these unique Virginia hotels, inns and B&Bs and explore one of the six winery clusters that are an easy drive from Arlington.
Around Charlottesville
Distance from Arlington: 2-2.5 hours
Crossroads Inn
Like many Virginia properties, Crossroads has hosted many prominent guests in its 200-year history, including Thomas Jefferson, Martin Van Buren and Teddy Roosevelt. But this intimate inn’s signature feature is its focus on the land. Crossroads shares ownership—and property—with Pippin Hill Farm and Vineyards, which offers guests cooking classes, farm workshops, estate tours and special wine pairings with lunch or dinner. Breakfast, prepared by a team overseen by Pippin Hill’s head chef, Victoria Cosner, features fresh eggs from the inn’s resident chickens, and each guest room comes stocked with treats for feeding the birds during your stay. Other vineyards within a 20-minute drive include the acclaimed Michael Shaps Winery, organic winery Loving Cup and Mountain & Vine Vineyards (formerly Delfosse Vineyards), which also has its own farmhouse and cabin for rent on site. 5010 Plank Road, North Garden, VA
Boars Head Resort
This sprawling Charlottesville resort sits in the heart of Central Virginia wine country, an easy drive from dozens of vineyards across Albemarle and Nelson counties, including King Family, Oakencroft, Knight’s Gambit and Stinson Vineyards. After a day of wine tasting you can continue the experience in the Mill Room Restaurant. (Pro tip: request an off-menu tasting from the bar’s extensive Virginia selections.) Boars Head often hosts wine events, including the gold medal celebration for Monticello Wine Week each summer. And with ample walking paths and hiking trails threading through the 600-acre property, there’s no better place to watch fall color sweep across the Blue Ridge foothills. 200 Ednam Drive, Charlottesville, VA
Other area properties to explore: Keswick Hall, for destination dining at Marigold by Jean-Georges Vongerichten; and Farmhouse at Veritas, a luxury bed-and-breakfast on site at Veritas Vineyards and Winery.
Around Orange / Barboursville
Distance from Arlington: 1 ½ – 2 hours
Inn Willow Grove
As temperatures cool, settle in with a glass of Cabernet Franc—Virginia’s signature red—and warm up by one of the many fireplaces scattered throughout the Inn at Willow Grove, a uniquely restored 250-year-old manor house and cottage lodging tucked away on 40 acres in Orange, Virginia. Willow Grove wears its dedication to wine proudly, with a Wine Spectator Award, year-round wine dinners and curated pairings with local wineries at its Vintage Restaurant and Pub. This fall, the inn’s weekday stay special sweetens the deal with a $250 resort credit—good toward dining or a visit to the full-service spa—plus extras like wine, beer or cocktail vouchers and chocolate-covered strawberries. Explore nearby wineries including the horse racing–themed Woodbrook Farm Vineyard; Chateau MerrillAnne, which specializes in fortified wines; historic Horton Vineyards; and Early Mountain Vineyards, which also has an on-site restaurant focused on seasonal produce. 14079 Plantation Way, Orange, VA
The Estate at Meander
New owner Eric Watson brings Virginia wine directly to his guests, stocking the vino list at Meander’s restaurant, Harvest & Hearth, with labels from nearby wineries like King Family, Barboursville and Prince Michel—including The Reverend, a private-label Bordeaux-style blend made for the property by DuCard Vineyards. This fall, Watson plans to add wine dinners and will continue to feature at least a pair of Virginia wines on the restaurant’s weekly-changing, multi-course estate dinner menu. Meander’s focus is on disconnecting and detoxing; you won’t find TVs or phones in most guest rooms, and this fall the spa will expand to include contrast therapy and thermal baths with mountain views. Book a midweek trip this fall for discounts on spa and stay packages. 2333 N. James Madison Highway, Locust Dale, VA
Other area properties to explore: Mayhurst Estate, a luxury bed-and-breakfast in Orange; Barboursville Inn & Cottages, the on-site lodging at renowned Barboursville Vineyards.
Around Middleburg
1 hour from Arlington
Goodstone Inn
Goodstone’s concierge team has mastered the art of private tastings, winery visits and customized wine-focused itineraries for guests eager to explore the local vineyards.  Woman-owned Cana Vineyards, Chrysalis Vineyards (known for its estate Norton) and adults-only 50 West Vineyards are all less than 20 minutes away by car. Grayson’s, the Wine Spectator award–winning on-site restaurant, boasts over 1,200 wine selections and sources many of its culinary ingredients directly from the 265-acre estate, including honey from its own apiary. Take one of the inn’s bikes out for a spin, or book a guided hike along Goodstone’s scenic trails.  36205 Snake Hill Road, Middleburg, VA
Red Fox Inn
This nearly 300-year-old inn in the heart of downtown Middleburg carries more than 50 Virginia wines by the bottle, including selections from nearby Greenhill Vineyards, Slater Run and Boxwood Estate Winery, which makes four private label selections for the inn. The family-owned lodging features two dining options—a formal dining room with a seasonal, fixed price menu, and elevated pub fare in the bar. (Think salt-and-pepper chips topped with caviar and portobello mushroom fries.) Overnight guests don’t have to go far for local flavor: bedside cookies and gourmet breakfast boxes are delivered right to your room. 2 E. Washington St., Middleburg, VA
Other area properties to explore: The ultra-luxurious Salamander Resort has a full equestrian center and offers ziplining under the stars this fall; Briar Patch B&B allows guests to bring their dogs along for an overnight stay.
Around Leesburg
Distance from Arlington: 45 minutes – 1 hour
Hotel BurgÂ
This classy Leesburg newcomer feels a world away, even though it’s barely out of town—and it’s already leaning hard into its wine country surroundings with a fall vineyard package that includes round-trip car service, a picnic lunch and a welcome bottle of wine. Ease into the weekend with a leisurely tasting at Zephaniah Farm, then pick up the pace at bustling Stone Tower Winery, where the vibe is upbeat. Then wind down with a pour of the signature sparkling Red Spark at Casanel Vineyards & Winery. Sll of these tasting rooms are less than 20 minutes from downtown Leesburg. If you return to town still thirsty, October One Vineyard‘s tasting room and shop is located a block from the hotel, helmed by Bob Rupy, one of the region’s best-known vintners. 208 S. King St., Leesburg, VA
Also consider: Affordable Lansdowne Resort offers a range of amenities, including several restaurants, pickleball and a spa, for an easy overnight or long weekend.
Around Winchester / Northern Shenandoah
Distance from Arlington: 1.5 hours
George Washington Hotel
This Hyatt-branded property sits in the heart of downtown Winchester, putting the northern stretch of the Shenandoah Valley Wine Trail within easy reach. Twenty minutes from the hotel, you can sip a wine found nowhere else in the state—the hybrid grape Arandelle—at Briede Family Vineyards, sample the many crisp expressions of Vidal Blanc at Valerie Hill Vineyard or pour a glass of James Charles Winery‘s 2023 Cabernet Sauvignon, a recent 89-point Wine Enthusiast pick. Back at the George Washington Hotel, unwind with live music in the Half Note Lounge or float in the spa’s Roman bath–style indoor pool. And since the hotel sits just off the city’s pedestrian mall, a great meal or an evening stroll through town is only steps away. 103 E. Piccadilly St., Winchester, VA
Also consider: In addition to a sumptuous breakfast, guests at the upscale inn L’Auberge Provençale in Boyce also receive a selection of house-made sweet snacks each afternoon.
Around Fauquier / Linden
Distance from Arlington: 1.5 hour
Glen Gordon Manor
This boutique inn has teamed up with newcomer Crimson Lane Vineyards (owned by Arlingtonians Tom and Deanna Herrity) on a package made for sipping and savoring. Guests start with a guided tasting and dessert in the winery’s hillside tasting room in Linden, then head back to Glen Gordon for a seasonal, five-course dinner with wine pairings at Houndstooth Restaurant, a dining room that’s racked up Wine Spectator’s Best of Award of Excellence year after year. Feeling adventurous? Glen Gordon will craft a custom itinerary to explore the region, whether that’s Rappahannock Cellars (also home to appointment-only Dida’s Distillery), Linden Vineyards, led by legendary Virginia winemaker Jim Law, or cozy Glen Manor Vineyards, which turns out some of the state’s finest bottles. Back at the inn, work off the day’s indulgences (or lean into them) with an in-room massage—the Tack Room Spa is getting a glow-up and set to reopen in early 2027—then explore the property’s 45 acres with the Blue Ridge Mountains as your backdrop. 1482 Zachary Taylor Highway, Huntly, VA
Also consider: The Marriott Ranch B&B Â in Hume offers horseback riding as one of the opportunities on the 4,000-acre property.
