The Best Inns in the Berkshires for Wedding Guests

So your friend's getting married and you need to find amazing inns in the Berkshires to stay in?

Honestly, picking the right place to stay can make or break your weekend. You don't want to end up at some sketchy motel off Route 7, trust me.

Here's the thing - the Berkshires aren't cheap during wedding season. But there are some genuinely amazing inns in the Berkshires that are worth the splurge. Plus, if you're already dropping money on a gift and potentially a rental car, you might as well stay somewhere that doesn't make you want to leave early Sunday morning.

Why Choose an Inn in the Berkshires for Your Wedding Stay?

Photo by: Stonover Farm

Honestly? Because hotels here are either chain places that could be anywhere, or they're booked solid.

The inns though - that's where the magic happens. Most of them actually get what it's like when you're dealing with wedding logistics. They'll hold your dress bags, they know which Uber drivers are reliable, and they won't judge you for stumbling in at 2 AM after the reception.

Plus, let's be real - half the fun of a Berkshires wedding is the whole New England vibe. You want those Instagram shots with the white picket fences and the fall foliage (if you're lucky with timing).

The good inns also know how to handle wedding groups. They'll actually coordinate with other guests from your party. Some even offer shuttle services, which is clutch when everyone's been drinking champagne since 3 PM.

Top Inns in the Berkshires for Wedding Guests

1. Stonover Farm

Photo by: Stonover Farm

Address: 169 Under Mountain Road, Lenox, MA 01240  Phone: (413) 637-9100 Website: stonoverfarm.com  Email: stonoverfarm@stonoverfarm.com

Okay, this place is gorgeous. Like, really gorgeous.

Those blue-trimmed buildings? Chef's kiss. The duck pond is legitimately peaceful, not just Instagram pretty.

Here's what you need to know: Stonover has five suites, so it's perfect if you're part of the wedding party or if a few couples want to stay together. The School House Suite is the best one - totally private and you get your own little cottage feel.

The downside? It's an investment for sure. We're talking luxury inn prices, not B&B rates. Also, they only do 12 weddings a year, so if you're looking to book, do it early.

But if you can swing it, you'll feel like you're staying in a Pottery Barn catalog. The kind where everyone's wearing cable knit sweaters and sipping cider.

2. The Inn at Stockbridge

Photo by: The Inn at Stockbridge

Address: 30 East Street, Stockbridge, MA 01262  Phone: (413) 298-3337 Website: stockbridgeinn.com  Email: innkeeper@stockbridgeinn.com

This is my go-to recommendation for most people.

Gary and Nicole (the owners) are genuinely nice humans who won't make you feel awkward if you show up looking like you've been traveling for six hours. They have 14 rooms across three buildings, so there's usually availability even during busy weekends.

The Barn Suites are where it's at if you're bringing your dog, yes, they're pet-friendly. The Main House rooms have that classic New England charm without feeling like a museum.

Pro tip: Their social hour isn't just crackers and wine. I'm talking actual cocktails and decent snacks. Perfect for a little pick-me-up before you head to the rehearsal dinner.

3. LakeHouse Inn

Photo by: LakeHouse Inn

Address: 615 Laurel Street, Lee, MA 01238  Phone: (413) 394-4256 Website: lakehouseinnlee.com  Email: innkeeper@lakehouseinnlee.com

Here's the thing about LakeHouse Inn - it's adults only. Which is either perfect or a total dealbreaker depending on your situation.

The lake views are legit, and they give you kayaks and paddleboards for free. Plus, they do this evening cognac tasting thing that sounds fancy but is actually just a nice way to meet other guests.

The location is solid - you're basically between Lee and Lenox, so you can get to most venues pretty easily.

What's not great? If you're under 21, you can't stay here. Period. Also, some people find the "intimate boutique experience" a little much. If you prefer to fly under the radar, this might not be your vibe.

But honestly, if you want to feel like you're in a lakeside movie montage, this is your spot.

4. Race Brook Lodge

Photo by: Race Brook Lodge

Address: 864 South Undermountain Road, Sheffield, MA 01257  Phone: (413) 229-2916 Website: rblodge.com  Email: info@rblodge.com

This one's for the outdoorsy people in your life.

I haven't stayed here personally, but my hiking buddy swears by it. It's more rustic than the other places... think "elevated camping" rather than "luxury retreat." The restaurant is supposed to be really good though, all farm-to-table stuff.

If the wedding party includes people who use words like "glamping" unironically, they'll love this place. Direct trail access, sustainable everything, and you'll probably see more wildlife than wedding guests.

5. The Red Lion Inn

Photo by: The Red Lion Inn

Address: 30 Main Street, Stockbridge, MA 01262  Phone: (413) 298-5545 Website: redlioninn.com  Email: info@redlioninn.com

Look, everyone knows the Red Lion. It's been here since 1773, which they'll definitely mention.

It's the classic choice - like, if you tell people you stayed at the Red Lion, they'll nod approvingly. The main building has that old-school New England thing down pat. Norman Rockwell literally painted this place.

It's big (108 rooms), so it can feel a little bigger than what you'd expect for an inn. The rooms vary wildly depending on which building you're in. So that's something to keep in mind.

The dining room is solid for a fancy dinner, but it's also traditional. Very "New England country inn" on the menu.

Best for: Parents and grandparents who want somewhere "nice" and "established." Not so much for people who want boutique vibes.

Tips for Booking Wedding Guest Accommodations in the Berkshires

Book early or prepare to drive from Springfield.

Seriously, the good places fill up fast. If you're looking at a Summer or Fall wedding, start calling in January.

Ask about group rates, but don't expect miracles.

Most places will give you something if you're booking multiple rooms. But we're not talking 50% off. More like a free continental breakfast or late checkout.

Get clear on transportation.

Some venues are in the middle of nowhere. Make sure you know how you're getting to and from the wedding. Uber exists here, but it's not like Boston - you might wait 45 minutes for a ride.

Check the cancellation policy.

Weather happens. Drama happens. Pandemics happen (unfortunately). Make sure you can get out of your booking if things go sideways.

Always ask about parking. Some of these historic inns have limited spots available.

Explore More Lodging Options in the Berkshires

If these don't work for you, check out berkshires.org/places-to-stay for more options.

There are definitely other nice places, but these are our top picks.

Don't forget to tell your guests about all the incredible activities in the Berkshires!

Plan Your Perfect Wedding Stay in the Berkshires

Here's the bottom line: picking the right inn in the Berkshires makes your whole wedding weekend better.

The Berkshires are beautiful, but they're even better when you have a cozy home base to come back to after dancing until midnight.

Ready to book the perfect spot for your wedding weekend? I've helped tons of couples figure out group accommodations for their Berkshires events that actually work. From negotiating group rates to coordinating shuttles, I know how to make the logistics seamless so you can focus on celebrating. Let's chat about your specific needs and get your guests sorted with amazing places to stay.

Still looking for a Berkshire wedding venue? Check out our list!

Interested in learning more about us before you reach out? Read about why we are the best wedding planners Massachusetts.