May 15, 2026

The Main Street Hospitality Problem in the Berkshires

If you've ever planned a Berkshires weekend, you've probably ended up with a shortlist that includes some combination of the Red Lion Inn, the Porches Inn at MASS MoCA, the Williams Inn, Race Brook Lodge, and maybe the Little Lion in Great Barrington. Five of the most-searched, most-reviewed, most-written-about hotels in the region.

What most Berkshires travel coverage fails to mention: all five are owned or operated by the same company. Main Street Hospitality Group, headquartered in Stockbridge, runs all of them. It is, functionally, the regional hotel chain of the Berkshires.

Related: see our newer guide on How Main Street Hospitality Came to Own the Berkshires.

This article is an honest look at what that means — for the properties themselves, for the region's hotel ecosystem, and for how we cover the Berkshires at Lehotelist.

The properties

Main Street Hospitality's current Berkshires portfolio, as best we can track it:

The Red Lion Inn (Stockbridge) — the flagship, 125+ rooms, arguably the most famous inn in the Berkshires.
The Porches Inn at MASS MoCA (North Adams) — 47 rooms directly across from the museum.
The Williams Inn (Williamstown) — 64 rooms built new in 2019 next to Williams College.
Race Brook Lodge (Sheffield) — a 33-room compound in the southern Berkshires.
The Little Lion (Great Barrington) — formerly The Briarcliff, rebranded under the group's ownership.

Five hotels, one company. That's more Berkshires inventory under shared ownership than any other boutique operator in the region — by a large margin.

Why it's not technically a chain (and why we treat it like one)

Main Street's defense — and it's a reasonable one — is that each property retains its own character. The Red Lion is still the Red Lion. The Porches looks like the Porches. There's no uniform design language, no shared reservation system in the way Marriott runs things, no "Main Street Gold Rewards."

The counter-argument is that a single management company running five of a region's most-booked hotels is, by any reasonable definition, a regional chain — regardless of whether the external brands look different. You are dealing with one set of owners, one operational team, one revenue-management strategy, one hiring pipeline, and one set of vendor relationships. That's the definition of a chain. The fact that the facades differ doesn't change the back-end reality.

Compare it to a different model. In the Hudson Valley, Foster Supply runs three properties (Kenoza Hall, Callicoon Hills, Debruce — all in the western Catskills). We treat Foster Supply portfolios as adjacent to independence but still inside our editorial focus at that three-property scale. Five properties is where we draw the line. The Lark Hotels group (north of us, in coastal New England) now runs dozens of properties under their "collection." That's clearly a chain. Five is the threshold, and Main Street is over it.

What the Main Street presence does to the region

Three effects that affect travelers whether they realize it or not:

1. SEO and booking funnel dominance. The Red Lion alone has a 150+-year brand. Combine it with four other heritage-adjacent names and you've got a search-result wall that's essentially impossible for a six-room independent inn to get around. "Best hotels in the Berkshires" lists are overwhelmingly written by people who monetize through Booking.com, where Main Street properties take a disproportionate share of the clicks. This is why half the "best of" lists you read are essentially Main Street's back catalog.

2. Revenue management homogeneity. Main Street's properties move their rates together in a way smaller independent inns don't. When Tanglewood season hits, the Red Lion, the Williams Inn, and the Porches all raise rates in roughly the same pattern at roughly the same time. Independent inns (Doctor Sax House, Stonover Farm, Granville House) price more idiosyncratically — sometimes much cheaper on a Thursday in late July, sometimes genuinely expensive on a random off-season weekend for local reasons. This is a small thing, but it's real: a region dominated by one operator has less price variation than a region with twenty genuinely independent owners.

3. The "if it's popular, it's probably Main Street" funnel. New visitors default to the most-reviewed, most-photographed, most-recommended hotel in a region. In the Berkshires that default-path leads, overwhelmingly, to a Main Street property. The traveler never learns that Tourists (independent) is ten minutes from the Porches. Or that Mezze Guesthouse is in Williamstown instead of the Williams Inn. Or that Granville House — a genuinely independent Michelin-Key five-room property — exists at all.

What our coverage does about it

On Lehotelist, we exclude Main Street properties from our editorial reviews and from our "best of" lists. Not because the properties are bad — several are genuinely good hotels — but because their ownership structure violates our editorial definition of independent (five properties or fewer, no outside chain management). We apply this rule consistently: we also exclude Lark Hotels properties, Auberge Resorts Collection properties, Salt Hotels, Faraway Hotels, and Aman.

What this means in practice: when you see our Best Independent Hotels in the Berkshires list, the Red Lion is not on it. Tourists is. Doctor Sax House is. Granville House is. Stonover Farm is. Birchwood Inn is.

Is this unfair to Main Street?

Not really. We're not saying their hotels are bad — we're saying they're part of a regional chain, which is editorially a different category than an owner-operated independent. Main Street is a well-run company. The Red Lion is a legitimate American heritage hotel. The Porches at MoCA is strategically placed. The Williams Inn has its moments. If you want to stay at one, the information is everywhere.

Our editorial job is to surface the other list — the fifteen-to-twenty Berkshires hotels that aren't Main Street, that are still run by families and small teams, and that don't have the SEO budget to dominate your search results. That list is what we cover.

What travelers should take from this

Three practical takeaways:

If a Berkshires hotel shows up on every "best of" list, check who owns it. Google "[Hotel Name] Main Street Hospitality." If it's one of theirs, that's not automatically bad — but it's information.
The genuinely independent Berkshires hotels are smaller, quieter, and harder to find. They don't show up at the top of Booking.com search. They show up on curated lists, in word-of-mouth conversations, and on niche sites like this one.
Pricing varies more on the independent side. A midweek in May at East Rock Inn or ButtonBall Inn can be 30-50% below the equivalent Red Lion night, and the experience is arguably more distinctive.