You’re driving up Route 7, the sun is dipping behind the jagged silhouette of Monument Mountain, and you see it. A long, low-slung building that looks like it was ripped straight out of a 1960s postcard. It’s the Briarcliff Motel in Great Barrington, or at least, that’s what the sign likely said when you first bookmarked it.
Honestly, things have changed.
The first thing you need to know—the "insider secret" that trips up half the people trying to book a weekend here—is that the Briarcliff is now technically The Little Lion. It’s part of the Main Street Hospitality group now, the same folks who run the legendary Red Lion Inn just down the road in Stockbridge. But despite the rebrand, locals and regulars still call it the Briarcliff. It’s got that specific DNA you can’t just erase with a new logo.
Not Your Grandma’s Roadside Motor Lodge
Most people hear "motel" and think of flickering neon, stale cigarette smoke, and carpet that hasn't seen a vacuum since the Nixon administration. The Briarcliff Motel (sorry, Little Lion) is the exact opposite. It’s what happens when a classic mid-century motor lodge goes to art school.
The vibe is sort of "retro-Scandi." Think Marimekko prints, bright punchy colors, and clean lines that make the rooms feel way bigger than they actually are. It’s cozy. It’s stylish. But let’s be real: it’s still a motel. You park your car right in front of your door. You can hear the gravel crunch when your neighbor gets back from a late dinner at Prairie Whale.
If you’re looking for a soundproof vault, go to a Marriott. If you want to feel like you’re in a Wes Anderson movie set in the Berkshires, stay here.
The Monument Mountain Connection
Location is basically everything in the Berkshires, and this spot is ridiculous. You are literally at the foot of Monument Mountain. You don’t even need to drive to the trailhead; you just lace up your boots and go.
It’s a 2.5-mile loop. The "Hickey Trail" is the steep one that gets your heart screaming, while the "Mohican Trail" is the more leisurely route. When you get to the summit—about 1,739 feet up—you get that panoramic view of the Housatonic River Valley that allegedly inspired William Cullen Bryant to write poetry.
The motel actually leans into this "base camp" identity. They have a massive communal fire pit that gets lit every night. There’s something kinda magical about sitting there with a complimentary s'mores kit, looking up at the mountain you just climbed, and realizing you haven't checked your email in six hours.
What’s the Deal with the Amenities?
Since the shift to the Little Lion branding, the service model has evolved. It’s definitely more "independent" now.
- Breakfast: You used to get this spread in the lobby. Now, it’s often a homestyle continental situation with local yogurt, granola, and Harney & Sons tea. Some guests have noted that the lobby isn't always "staffed" in the traditional sense, using more of a contactless check-in system.
- The Red Lion Perk: This is the big one. Because they’re sister properties, staying at the Briarcliff usually gives you access to the Red Lion Inn’s pool and hot tub in Stockbridge. It’s a five-minute drive. You get the hip, affordable motel room but the "fancy hotel" pool access. It’s a total pro move.
- Pet Friendly: They don’t just "allow" dogs; they basically roll out the red carpet. They have "adventure boxes" for pups with organic treats and toys. Unlike many places in Great Barrington that charge a $75 "cleaning fee" that feels like a shakedown, the Briarcliff has historically been much more chill about four-legged guests.
The Truth About the Rooms
Let’s talk brass tacks. These rooms are "curated," but they are simple.
You’re going to get a flat-screen TV, probably an old-school iPod dock (a weirdly charming relic), and very comfortable beds. But you aren't getting a massive marble bathroom or a kitchen. Some of the rooms have refrigerators and microwaves, but it varies.
The walls? Yeah, they’re a bit thin. You’re in a building from the 60s. If the person next door has a loud laugh, you’re going to hear it. Most people who stay here don't mind because they're spending the day at Tanglewood or hiking, but if you’re a light sleeper, bring a white noise machine or some earplugs.
Where to Eat When You’re Bored of Granola
Great Barrington is a massive foodie hub. You’re five minutes from downtown, which means you have options.
- Bizen: It’s on Railroad Street. It’s gourmet Japanese and sushi that feels like it belongs in Kyoto.
- Number Ten: If you want a steak and a stiff cocktail in a place that feels like a vintage tavern, this is it.
- Moon Cloud: Perfect for charcuterie and clever drinks.
- Soco Creamery: Do not—I repeat, do not—leave town without getting a scoop of Dirty Chocolate.
The "Is It Worth It?" Factor
The Berkshires have become incredibly expensive. You can easily drop $600 a night at a B&B in Lenox where you’re forced to have breakfast with strangers at a communal table.
The Briarcliff Motel Great Barrington offers a middle ground. It’s usually priced significantly lower than the full-service inns, yet it feels more "boutique" than the chain hotels out on the highway.
Is it perfect? No. Some guests have complained about the lack of an on-site innkeeper 24/7 or the "no-frills" nature of the tech. But for a specific type of traveler—the hiker, the dog owner, the person who appreciates a Marimekko pillowcase and a roaring fire—it’s arguably the best value in South County.
Actionable Tips for Your Stay
- Book the King Room: If you can, grab a King. They tend to feel a bit more updated and spacious.
- Check the Event Calendar: If you’re visiting for Tanglewood (about 15 minutes away), book months in advance. This place fills up the second the BSO announces their schedule.
- Request the "Mountain View" Side: While all the rooms face the same general direction, the ones further from the road are quieter and give you a better "forest" feel.
- Bring a Flashlight: The grounds are beautiful at night but it gets dark in the Berkshires. If you’re heading to the fire pit, you’ll want the extra light.
- Download Offline Maps: Cell service near Monument Mountain can be spotty. Don't rely on your GPS to find your way back from a late-night dinner in Sheffield.
The Briarcliff (Little Lion) isn't trying to be a five-star resort. It’s a launchpad. It’s a place to crash after a long day of exploring the hills, drinking local cider, and breathing in air that actually smells like pine trees instead of exhaust. Just remember: it's a motel. Embrace the nostalgia, grab a s'mores kit, and keep your expectations as grounded as the mountain across the street.