The Best Luxury Hotels & Boutique Inns Near Wintergreen Resort

As someone who’s lived in the Blue Ridge Mountains for years, I’ve lost count of how many weekends I’ve spent up at Wintergreen Resort. Whether it’s carving fresh powder in the winter, hiking and mountain biking in the warmer months, or just soaking in those sweeping views with a glass of local wine—this place never gets old. But let me tell you, having the right hotel nearby can make your Wintergreen getaway truly unforgettable.

I’ve stayed at (and recommended) just about every luxury hotel in the area, and over time I’ve narrowed it down to a handful of top picks. These are the places that combine mountain charm with modern comfort, and that I keep coming back to—sometimes for the views, sometimes for the hot tubs, and sometimes just because they’re that relaxing.

So if you’re headed to Wintergreen and looking for a cozy, high-end place to crash after a day on the slopes or trails, here’s your local-approved list.

Afton Mountain Inn — A Blue Ridge Boutique Favorite

10273 Rockfish Valley Hwy, Afton, VA 22920
AftonInn.com
12 miles from Wintergreen Resort
From $195 per night

This is hands-down my top recommendation for anyone visiting Wintergreen. I’ve sent friends, family, and even a few ski instructors here over the years, and everyone comes back raving. Afton Mountain Inn is tucked along Route 151—right in the heart of Virginia wine and craft beer country—with mountain views in every direction and some seriously impressive amenities for such a small inn.

The first time I stayed, I was blown away by how peaceful it was. The inn sits on 10 acres, complete with a crystal-clear creek and a private nature trail that winds through the woods behind the property. After a long day of skiing, there’s nothing better than grabbing a blanket and relaxing on one of the romantic porch swings—or hopping in one of the two hot tubs. I’ve also spent evenings by the fire pits, sipping wine from nearby Veritas Vineyard and swapping stories with fellow guests.

The rooms are beautifully redone, with big comfy beds and thoughtful touches that make it feel more like a boutique retreat than a typical hotel. And if you’re traveling with a group, the two-bedroom villa is perfect for couples or families.

Driving to Wintergreen Resort from Here:

Head south on Route 151 for about 10 scenic miles, then take a quick turn onto Route 664 (Beech Grove Rd). That twisty mountain drive leads straight up to the resort. Plan for about 20 minutes—plus a few extra if you stop at a cidery or overlook along the way (and you should).

What Makes Afton Mountain Inn Special?

• Resort-Style Pool & Hot Tubs – Tucked into the hillside and surrounded by trees, the resort-style pool at Afton Mountain Inn is a true standout—perfect for lazy afternoons or cooling off between tastings. Two hot tubs offer the ultimate relaxation, whether you're unwinding after a day on the wine trail or stargazing with a glass of local red in hand. Not many places along Route 151 near Wintergreen offer amenities like this—it’s a total game-changer for guests looking to mix adventure with a bit of luxury.
  
  

• Private Nature Trail – Just behind the inn, a peaceful walking path winds through the woods and along a spring-fed creek. It’s one of our favorite hidden gems. The sound of the water, the dappled light through the trees, and the occasional deer sighting make it feel like your own private retreat. There’s nothing better than enjoying a quiet morning coffee by the creek, with the soft sound of the water flowing by.
  
  

• Fire Pits & Porch Swings – When the sun goes down, the fire pits come alive. Spread out across the property, they’re ideal for gathering with friends, roasting marshmallows, or simply soaking in the peaceful night air. Romantic porch swings dot the grounds as well—perfect for two, especially with a blanket and a bottle of wine.
  
  

• Chic Rooms & a Two-Bedroom Villa – Each suite is thoughtfully designed with a mix of rustic charm and modern comfort. Think cozy linens, curated décor, and all the little touches that make a stay feel special. For couples, it feels much more intimate and unique than a big-name hotel—it’s the kind of place where the details actually matter. Meanwhile, the two-bedroom villa is great for families or groups—it has a private entrance, spacious living area, and its own kitchen, giving you the best of both worlds: the comforts of home and the perks of an inn.
  
  

• Close to Everything – Afton Mountain Inn is right in the heart of it all. You’re just minutes from Veritas Vineyard, Blue Mountain Brewery, and countless other favorites along Route 151. And if you’re heading to Wintergreen for skiing, hiking, or a mountaintop dinner, it’s a quick and scenic drive up the mountain.

Why Stay Here?

Because it’s the ideal home base for your Wintergreen adventure—without giving up comfort or style. Just a short drive from the resort, Afton Mountain Inn lets you spend your days skiing, snowboarding, hiking, or golfing at Wintergreen, then come back to a peaceful retreat with all the perks.

Instead of crowded hotel lobbies, you’ll unwind in a hot tub, sip wine by the fire pit, or relax on a porch swing under the stars. The chic rooms and cozy villa offer a boutique feel, while the resort-style hot tubs, pool, nature trail, and creekside seating make it easy to recharge between mountain outings.

It’s the best of both worlds: close to the slopes, but far from the crowds.

The Iris Inn — A Luxe Mountain Escape with Million-Dollar Views

8200 Bear Ridge Rd, Waynesboro, VA 22980
IrisInn.com
10 miles from Wintergreen Resort
From $239 per night

If you’re looking to spoil yourself a little (or a lot), The Iris Inn is one of my top picks. I first stayed here years ago for a last-minute weekend getaway, and now it’s one of my go-to recommendations for anyone who wants comfort, privacy, and those wow-worthy mountain views. It’s perched up on a ridge just outside Waynesboro, with a panoramic view of the Shenandoah Valley that honestly never gets old—sunrise, sunset, fog, snow—it’s always special.

One of my favorite things? The rooms. Or I should say cabins, cottages, and suites. They’re not just pretty—they’re packed with thoughtful touches like fireplaces, soaking tubs, wine fridges, and private decks. I stayed in one of the glass-front cabins once in the fall, and I’ll never forget waking up to the trees lit up in orange and gold. Pure magic.

The main inn has a cozy lodge vibe with a big stone fireplace and the friendliest team you’ll ever meet. One time I left my phone charger behind and they mailed it back with a handwritten note and a little packet of local tea. That’s the kind of place this is—small touches that leave a big impression.

Driving to Wintergreen Resort from Here:

Hop on Route 250 west, then turn onto Route 151 south toward Beech Grove Road (Route 664). It’s a smooth and scenic drive—expect about 20 minutes. The Blue Ridge Parkway is also nearby, so you’ve got some stunning detour options if you’re in the mood to explore.

What Makes The Iris Inn Special?

• Modern Cabins, Cottages & Suites – These aren’t your average mountain rooms. Think floor-to-ceiling glass, sleek interiors, and private decks that feel like you’re floating in the trees. Perfect for couples or solo getaways. Some have soaking tubs, fireplaces, and even massage chairs. Yes, please.
  
  

• Unmatched Views – The view from The Iris Inn is easily one of my favorites in the area. I’ve sat on the porch with a glass of wine and watched thunderstorms roll in over the valley—unforgettable. You can see for miles, and every season brings its own kind of beauty.
  
  

• Private & Peaceful Vibe – Even when it’s booked up, it never feels crowded. The layout is super private, and the whole place feels like a hidden mountain retreat. Great for decompressing after a busy day on the slopes or trails.
  
  

• Breakfast That Hits the Spot – Their breakfast game is strong. Local ingredients, made-to-order, and served in a sunny dining room with more of those killer views. I still think about the goat cheese frittata I had one morning—10/10.
  
  

• Hot Tubs & Fire Pits – A few of the cabins have private hot tubs (yes, you want one), and there are fire pits where you can toast marshmallows or just hang out under the stars. One chilly evening I sat out there wrapped in a blanket with a spiked hot cider—it was heavenly.

Why Stay Here?

Because it’s like having your own luxury treehouse just minutes from Wintergreen. Whether you’re skiing, hiking, or just escaping for the weekend, The Iris Inn gives you the peace and privacy you want with high-end comfort and style.

It’s especially great for couples—romantic, quiet, and way more memorable than a chain hotel. But I’ve also seen small groups and families enjoy the cottages, which give you a little more space while still soaking in all the views. And hey, if you’ve got someone to impress, this place delivers.

Boar’s Head Resort — Classic Virginia Luxury, Just Outside Charlottesville

200 Ednam Dr, Charlottesville, VA 22903
BoarsHeadResort.com
26 miles from Wintergreen Resort
From $249 per night

Boar’s Head is one of those iconic places that locals grow up hearing about—and for good reason. It’s where you go when you want to treat yourself and still feel connected to Virginia’s natural charm. I’ve stayed here for weddings, conferences, and even a “just because” weekend when I needed a little reset. And every time, it feels like stepping into a slice of Southern hospitality, polished up with modern flair.

The grounds are beautiful—rolling hills, walking trails, a peaceful lake—and the rooms are recently updated, with cozy touches like wood-beam ceilings, plush beds, and big windows that look out over the golf course or gardens. I once had a room with a fireplace and a private porch where I drank coffee and watched the morning mist roll over the foothills. It was the calmest I’ve felt in months.

The resort is owned by the University of Virginia Foundation, so there’s a bit of collegiate pride sprinkled throughout, but it’s far from stuffy. The vibe is relaxed and refined—a little upscale, but totally welcoming.

Driving to Wintergreen Resort from Here:

Head west on I-64, then hop on Route 151 south to Beech Grove Road (Route 664) for that scenic mountain climb. The whole drive takes about 40–45 minutes, and it's honestly a lovely way to ease into the Blue Ridge mindset. Bonus: you’ll pass breweries like Pro Re Nata and wineries like Septenary on the way.

What Makes Boar’s Head Resort Special?

• Full-Service Luxury with Local Character – You get the crisp sheets, spa treatments, and fine dining, plus walking trails, historic charm, and that friendly Virginia welcome. It’s a nice balance if you want a classic resort experience without feeling like you could be anywhere.
  
  

• The Spa at Boar’s Head – One word: heavenly. I’ve gotten massages, facials, and even a pedicure here—and walked out floating every time. They use natural, locally inspired products and the setting is super serene.
  
  

• Racquet & Paddle Sports Galore – This place is a dream if you’re into tennis, squash, or pickleball. The facility is huge (UVA’s team trains here), and you can book lessons or clinics if you’re feeling sporty. My cousin came to visit, played pickleball for two days straight, and still talks about it.
  
  

• Birdwood Golf Course – Even if you don’t golf, you’ll love the views. The course was redesigned recently and is stunning. If you do golf, you’ll be in heaven. My dad called it one of the best public courses he’s ever played.
  
  

• Dining with a View – The Mill Room is the main restaurant, and it’s everything you’d want for a romantic dinner or a classy night out—elevated Southern food, local wines, and a patio that overlooks the lake. I still think about their she-crab soup and house-made bread.

Why Stay Here?

Because sometimes you want the full resort experience—without giving up charm and character. Boar’s Head is ideal if you want a little luxury while being close to both Charlottesville and the mountains. It’s the kind of place where you can spend the morning on the golf course, the afternoon exploring wineries, and the evening soaking in a spa tub or sipping bourbon by the fire.

It’s a bit farther from Wintergreen, but I know plenty of folks who stay here for ski weekends and just enjoy the extra drive as part of the adventure. It also makes a great “first night” stop if you’re flying into Charlottesville or driving from Washington D.C. and you want to unwind before heading into the mountains.

Whether you’re here for a romantic getaway, a wedding, or a wellness retreat, Boar’s Head delivers classic Virginia elegance—plus the kind of hospitality that keeps you coming back.

The Inn at Stinson Vineyards — Vineyard Views & Mountain Vibes

4744 Sugar Hollow Rd, Crozet, VA 22932
StinsonInn.com
18 miles from Wintergreen Resort
From $265 per night

If you’ve ever dreamed of waking up in a vineyard with the Blue Ridge Mountains in your backyard, this is your spot. The Inn at Stinson Vineyards is a modern, stylish little hideaway nestled above one of my favorite family-run wineries in Crozet. It’s peaceful, romantic, and absolutely stunning—especially in the fall when the leaves turn gold and the fog rolls in over the vines.

I stayed here last spring for a quick weekend getaway, and I’m still thinking about the mornings on the wraparound porch with a warm croissant and the soft hum of birdsong in the background. It’s quiet here, but not far from the action. You’re just a 30-minute drive from the slopes at Wintergreen, so it’s a great home base for skiing, hiking, or just exploring the mountain without staying on the mountain.

Driving to Wintergreen Resort from Here:

You’ll cruise down some of the prettiest roads in Virginia—Route 810 to Route 151 to Beech Grove Road (Route 664). It’s about a 30–35 minute drive, depending on how often you stop for photos or cider. Honestly, I always build in time to swing by Bold Rock or grab a snack at Blue Ridge Pig. Trust me—you’ll thank me later.

What Makes the Inn at Stinson Vineyards Special?

• On a Vineyard. Literally. – You’re staying right above the tasting room at Stinson Vineyards, which means you can roll out of bed, grab a glass of rosé, and take in the view. It’s such a treat to be able to walk the vines in the morning, then come back for a tasting flight in the afternoon—no driving required.
  
  

• Modern Farmhouse Style – The Inn itself is gorgeous. Think crisp white walls, reclaimed wood beams, curated artwork, and oversized windows with mountain views. It feels fresh and stylish, but still super cozy. I loved how quiet it was at night—no traffic, just crickets and stars.
  
  

• Gourmet Breakfast, Local Touches – Breakfast here isn’t your average muffin-and-OJ affair. They serve up locally sourced, chef-prepared options like farm egg frittatas, fresh pastries, and seasonal fruit. One morning, we had the fluffiest lemon ricotta pancakes with blueberry compote and I’m still trying to recreate them at home.
  
  

• Perfect for Couples – With just four rooms, it feels intimate and special—ideal for a romantic getaway. I stayed in the Piedmont Room and loved the freestanding soaking tub and private balcony. But honestly, every room here is a win.
  
  

• Close to Wintergreen, Without the Crowds – One of the best parts? You’re tucked away in peaceful Crozet, but still an easy drive to Wintergreen Resort. Spend your day skiing or hiking the Blue Ridge trails, then return to the inn for wine, a soak in the tub, and some serious R&R.

Why Stay Here?

Because it gives you the best of all worlds: vineyard serenity, boutique luxury, and easy access to the slopes. The Inn at Stinson Vineyards is perfect if you’re looking for a quieter, more romantic alternative to the resort hotels—but still want to be close enough to hit the slopes or trails at Wintergreen.

It’s a little off the beaten path, but that’s part of the charm. Whether you’re sipping wine by the fireplace, watching the sunrise over the vines, or bundling up for a Blue Ridge adventure, this place makes it easy to relax and reconnect.

The Farmhouse at Veritas — Luxury Lodging in the Heart of Wine Country

72 Saddleback Farm, Afton, VA 22920
veritasfarmhouse.com
13 miles from Wintergreen Resort
From $260 per night

If you’re looking to pair your Wintergreen trip with fine wine, farm-to-table meals, and a seriously stunning setting, The Farmhouse at Veritas is a dream come true. I always recommend it to couples and small groups who want a touch of romance and refinement without sacrificing easy access to the slopes or trails.

The Farmhouse is part of the award-winning Veritas Vineyard & Winery, which means you’re waking up among rows of vines with misty Blue Ridge views and spending your evenings sipping wine just steps from your room. The rooms themselves are beautifully restored—think country inn meets boutique hotel—with cozy linens, thoughtful decor, and that unmistakable vineyard charm.

What really sets it apart, though, is the dining experience. Breakfast is included and is absolutely top-tier (I’m still dreaming about the homemade scones I had there last fall), and you can reserve a seasonal prix-fixe dinner in the evening, cooked with ingredients from the surrounding farm and paired perfectly with Veritas wines. It’s the kind of place where you slow down, eat well, and actually feel like you’re on vacation.

Driving to Wintergreen from The Farmhouse

It’s a scenic, no-stress ride—just hop on Route 151 south for about 10 minutes, then turn onto Beech Grove Road (Route 664) and follow the curves up to the mountain. You’ll hit Wintergreen in around 20 minutes, but I always recommend building in time for a quick stop at Blue Toad Cidery or an overlook along the way.

What Makes The Farmhouse at Veritas Special?

• Winery Setting – Staying here means you’re steps away from one of Virginia’s most celebrated vineyards. Enjoy wine tastings, vineyard strolls, and stunning sunsets right outside your door.
  
  

• Gourmet Dining – Breakfast is always included, and you can book an intimate, multi-course dinner made with local ingredients. It’s like having your own private chef in the mountains.
  
  

• Refined Rooms – Each of the eight rooms (plus a private cottage!) is individually styled with antique touches, plush bedding, and vineyard views. It’s elegant without being stuffy.
  
  

• Peaceful Vibe – While it’s just minutes from Route 151 and Wintergreen, the Farmhouse feels like a true escape. Perfect for couples, anniversaries, or a relaxing weekend away from it all.

Why Stay Here?

Because it’s the best of both worlds: a luxury wine country experience and easy access to mountain adventures. Spend your day skiing or hiking at Wintergreen, then come back to a slow, wine-filled evening under the stars. For those who like their getaways with a little extra flavor (and a fantastic wine list), The Farmhouse at Veritas is tough to beat.

More Places to Stay: Vacation Rentals Near Wintergreen Resort

If you're planning a trip to Wintergreen, vacation rentals are also a popular and smart choice. Whether you're escaping for a romantic ski weekend or bringing the whole crew for a mountain getaway, there’s something for every style and budget. These homes offer the kind of comfort and flexibility hotels can’t match—like private hot tubs, full kitchens, fireplaces, and room to spread out.

You’ll find everything from slope-side condos with walkable access to the lifts, to secluded A-frame cabins tucked into the trees. Want a big mountain house with a game room and fire pit? We’ve got those, too.

Head over to our Best Wintergreen Vacation Rentals page to explore hand-picked stays hosted by locals who know the area well. We’ve highlighted the best options for couples, families, and large groups—plus tips on how to pick the perfect one for your trip.

Final Thoughts

Whether you’re heading to Wintergreen for a ski trip, a summer hike, or just some mountain R&R, there’s a perfect hotel nearby for every vibe. My personal favorite? Afton Mountain Inn. Between the hot tubs, fire pits, and unbeatable location close to Wintergreen, it’s just the kind of place that makes you feel instantly relaxed. But all the hotels above offer something special—and you really can’t go wrong.

So pack your hiking boots or your ski gear, book one of these beautiful stays, and come fall in love with this little slice of the Blue Ridge. I’ll see you on the slopes—or maybe at the wine bar afterward. Cheers!