Great Barrington MA Report: AirROI Pins, Not Leftover Occupancy

Thomas Garner
Aug 15
12 min read

Updated: 10 hours ago

Hikers on the trail toward the summit of Monument Mountain in Great Barrington, Massachusetts. Unsplash, location-tagged Great Barrington.

Great Barrington, MA is a southern Berkshires town with its own AirROI extract, its own 2022 short-term rental bylaw, and its own Main Street / Railroad Street walk. It is not Lenox. It is not Stockbridge. It is not a Berkshire County average dressed up as a town figure. Lenox shouldn't be blended into Great Barrington's named-town AirROI figures and relabeled as “the southern Berkshires.” If you want a comparison post later, cite both extracts on both sides.

This report uses one locked AirROI pull: Airbnb-only, trailing twelve months August 2025-July 2026, updated 2026-08-08,. Advertised daily rate $399, and occupancy 37.4%, and formula month. Median per month. Two-unit annual. Peak month August at. Peak-three August, October, and July, and professionally managed share 12.7%. Eight-plus bedrooms are the mode at 34.9%; six-plus is 54.8%. Leave out unverified a newer ADR. Do not blend a Lenox or Stockbridge sample into these cells.

The rest of this cluster will cover the bylaw, visitor-economy tables, and what guests actually type. This page is the market frame: what the extract says, what the town wrote down in 2022, and what an one-to-three-property independent host can use without turning a county tourism brochure into a rent roll. This page only needs the extract’s peak-three and the instruction: Keep your listing for August and October honesty, then decide what July and the shoulder actually do on your own folio.

What This Extract Is , and What It Is Not

AirROI’s Great Barrington page is a platform sample of Airbnb listings attributed to this town. It is not a town clerk census. It is not a Massachusetts Department of Revenue filing extract. It is not the same file as Lenox (a separate CLEAR town on the same 2026-08-14 filter, median , not this cluster). The occupancy figure is 37.4%. The formula month is. The median is per month. Those two monthly figures are not interchangeable, and median is the middle listing in the sample. Formula month is a constructed monthly from the extract’s method. Use the one you mean, and say which one you used.

n=166 is the sample size as of the 2026-08-08 update. It is large enough to talk about peaks and bedroom mix. It is not large enough to pretend every Railroad Street walk-up and every Monument Mountain driveway listing behaves the same. Professional management is 12.7% of the sample. That is a thin PM layer. Most of the extract is independent. That matches a host-written cluster, not a franchise playbook. What this extract does not give you: a Great Barrington town visitor-spend line, an official occupancy series from the Selectboard, a sale-price median for houses that can legally register, or a 2025 ADR. If a pitch deck assigns Berkshire County tourism to your three-bedroom, that assignment is an assumption.

The Peak-Three Calendar and Why 37.4% Is a Season Story

The locked TTM’s three strongest months are August, October, and July , in that order. August is the peak cell at in the extract. That is summer demand in a southern Berkshires town that guests treat as a weekend and week-long base, not a ski-in address. October is foliage and the second peak, and july is the third. The calendar is summer-plus-fall, and it is not a four-season machine. Mud season and midwinter are not in the peak three. Do not staff, price, or underwrite as if every month is August.

A host who annualizes August will overstate the year. A host who treats named-town occupancy pins as of 2026-07-31 as “the market is dead” is ignoring that the nights cluster in a few months.seasonality postin this cluster will walk the calendar month by month. This page only needs the extract’s peak-three and the instruction: Keep your listing for August and October honesty, then decide what July and the shoulder actually do on your own folio. Tanglewood is Lenox. Do not put a Tanglewood weekend calendar on a Great Barrington URL as if the lawn were on Railroad Street. If a guest asks, it is a drive, and name the drive when you have measured it. Leave out unverified a town-level Tanglewood occupancy.

Statewide hotel series and Berkshire visitor-economy tables will not tell you whether 37.4% is “good.” They will tell you that Massachusetts still has a large visitor economy. VisitMA’s 2024 Economic Impact Report put direct visitor spending at $24.2 billion statewide in calendar year 2024, up 2.3% (visitma.com/media-industry-portal/2024-economic-impact-report/). That is a state figure, and it is not Great Barrington occupancy. 1Berkshire, the official regional tourism council for Berkshire County, has published county-level visitor-economy figures in prior years , including a 2022 review that put direct visitor spending over $610 million and total economic impact around $900 million for the Berkshires (1berkshire.com, January 2023 review of the 2022 economy). Those are county numbers. They include Pittsfield, North Adams, Lenox, Stockbridge, and every other town. They are not a Great Barrington ADR.

37.4% on an Airbnb-only TTM with a summer-fall peak-three is consistent with a market that fills when the town is actually busy and sits quieter when it is not. Compare it to your own trailing twelve, not to a ski town’s winter occupancy and not to a Woodstock village cap market. The two-unit annual in the extract is. That is a constructed annual from the sample method, not a promise that two registered units will clear that number after tax, registration, and empty January weeks. Use it as a scale check. Do not put it in an offer memo as “the town average.”.

Bedroom Mix and a Thin PM Layer

Eight-plus bedrooms are the mode at 34.9% of the sample. Six-plus is 54.8%, and this is not a studio-and-one-bedroom factory. The listings guests compare in Great Barrington tilt large: houses that can take a family reunion, a wedding overflow, or a multi-generational foliage week. That mix changes marketing and operations. A two-bedroom over a shop on Railroad Street is not competing with an eight-bedroom on the same search page unless you force the comparison. Keep the listing for the house you have. Do not copy eight-bedroom amenity language onto a two-bedroom because the mode is large.

It also changes the bylaw conversation. The town’s the matching section above path (Annual Town Meeting, June 2022; effective January 1, 2023) lets an owner register only one dwelling unit as a short-term rental. “Up to two bedrooms in a dwelling unit or an entire secondary unit on the same parcel” may be registered by right, with an unlimited-day calendar if the owner is residing on premises, and a 150-day cap if the owner is not (townofgbma.gov, the matching section above). A large whole-house listing that is not owner-on-premises is a 150-day product. Do not underwrite 365 nights on a house the bylaw will not let you run 365 nights.

Theregulation postin this cluster is the full bylaw walk. This page only needs the market implication: the sample’s large-house mode and the town’s one-unit / 150-day rules are the same conversation. 12.7% professionally managed is not a managed-resort town, and most of the sample is independent. Cleaning, photography, and calendar work still happen, and they happen in the owner’s name. The bylaw is explicit that an owner may hire a property management company to list and manage, but the registration must be in the owner’s name (the matching section above, townofgbma.gov).

That is why this cluster is written to an one-to-three-property host, not to a 20-unit operator. If your model needs twenty identical units in one town, Great Barrington’s one-STR-per-owner rule is the first no. If your model is one registered house you can actually operate, the AirROI extract is a demand check and the bylaw is the operating envelope. Do not read 12.7% PM as “there is no competition.” Independent listings still compete on photos, copy, and honesty about Monument Mountain versus a Stockbridge museum drive. Do not read it as “hire a coastal PM at 25% because the town is unsophisticated.” The extract does not support that sentence.

Great Barrington Is Not Lenox, Stockbridge, or a County Average

Town of Great Barrington ≠ Stockbridge ≠ Lenox ≠ Sheffield ≠ West Stockbridge. Guests blur them because Route 7 does, and your listing should not. Norman Rockwell Museum is Stockbridge, and tanglewood is Lenox. Mass MoCA is North Adams, and those are drive-to search terms. They are not walk-from-Railroad-Street amenities, and the visitor guide and.overlooks posts will name what is actually in town , Monument Mountain, the Housatonic, downtown / Railroad Street, Butternut if it is still operating under its current name the week you publish.

Lenox is a separate CLEAR AirROI town on the same 2026-08-14 filter, median per month. Lenox shouldn't be blended into Great Barrington's named-town AirROI figures and relabeled as “the southern Berkshires.” If you want a comparison post later, cite both extracts on both sides. This report does not smuggle Lenox nights into GB cells. Berkshire County visitor spending is an useful floor for “people come here.” It is not your occupancy. When 1Berkshire or VisitMA publishes a county or state figure, quote the geography and the year. Do not Keep “Great Barrington’s $610 million visitor economy.” That sentence is false on the public record we have.

The 2022 Bylaw as a Supply Rule, Not a Village Cap

Great Barrington does not have a Woodstock-style 55-permit ceiling in the the matching section above text on the town site. What it has is stricter in a different way: annual registration with the town and with the Massachusetts Department of Revenue; one dwelling unit per owner; a 150-day limit when the owner is not on premises; a ban on corporate-owned units; LLC or Trust ownership only when every member is a natural person; no affordable or income-restricted units; no offering an unit that is already under a long-term lease (townofgbma.gov/378/Article-25-Short-Term-Rental-Bylaw-Summa, adopted at Annual Town Meeting June 2022, effective January 1, 2023).

The town’s registration hub says the bylaw requires every short-term rental to be registered, even if it will only be rented one night per year (townofgbma.gov/377/Short-Term-Rental-Registration-Hub). Hotels, motels, bed and breakfasts, and lodging houses already licensed with the town are told they do not need this STR registration if they advertise on short-term sites. The town’s GovOS portal FAQ, checked August 2026, lists a $200 registration fee (townofgb.munirevs.com/faq/). The bylaw itself gives the Selectboard authority to set fees. Confirm the current fee in the portal or with the Selectboard office () before you put $200 on a spreadsheet as eternal. This is not a “no rules” Berkshire town. It is a registration-plus-day-cap town. Scarcity here is the one-unit rule and the 150-day off-premises cap, not a numbered permit lottery. The investment and regulation posts will unpack that. The market implication is: the AirROI sample already lives inside that envelope. New supply is not unlimited just because there is no “55” in the bylaw.

What a Host Can Use , and What We Do Not Know

Use the extract as a demand-durability check. August, October, and July are when the sample makes money. Price those months from your own booked-and-blocked history once you have a year. Until then, do not assume $399 ADR is your house. That is the sample advertised daily rate, not an appraisal. Use the bylaw as the operating envelope before you furnish. If you cannot register, or if you need 200 off-premises nights, the rest of the math is a second-home budget. the matching section above is on the town website, and read it. The regulation post is the host translation.

Use Massachusetts tax as a net-income input, not as folklore. The Department of Revenue’s room occupancy page states a 5.7% state room occupancy excise (mass.gov/info-details/room-occupancy-excise-tax). Cities and towns may add a local option up to 6%. Confirm Great Barrington’s current local option on the DOR Municipal Databank before you model net. Do not copy a 2017 newspaper sentence as the 2026 rate. Use place names guests type. Railroad Street and Main Street are the walk. Monument Mountain is the in-town hike (Unsplash and trail pages locate the summit trail in Great Barrington). Butternut is the local hill if it is open the week you Keep , confirm the current operating name and official page. Do not lead with a Stockbridge museum photo.

The two-unit annual is a sample construct. After one registered unit (the bylaw’s limit per owner), you do not get a second Great Barrington STR by buying another house in your own name. Plan one unit. If you want two towns, that is two registrations in two governments. There is no official 2024 “Town of Great Barrington visitor spend” line in the VisitMA statewide report or in 1Berkshire’s county Keep-ups that we are using here. If a later town or county table publishes one, date it. Leave out unverified it for this page.

There is no official town occupancy series that matches AirROI’s 37.4%. Do not reconcile them, and they are different datasets. The $200 portal fee and the Selectboard’s fee schedule can move. Confirm, and butternut’s operating status and trade name can move. Confirm on the official ski-area page the week you mention it. How many units are actually registered with the town versus how many appear in AirROI is not a public reconciliation in the sources above. Leave out unverified a “compliance rate.” A 2025 or 2026 town-level visitor-spend table is not in hand. Statewide 2024 spending is, and county historical spending is. Keep the geography on the number.

The rest of this Great Barrington cluster is built to be used with this page: themarket reportand theregulation post,tourism data, thevisitor’s guideand theoverlooks guide,startup costand thefinancing post, andhow to marketthe listing without moving Tanglewood onto Railroad Street. This page is the market frame: what the extract says, what the town wrote down in 2022, and what an one-to-three-property independent host can use without turning a county tourism brochure into a rent roll.

Frequently Asked Questions

Is the $399 ADR a Great Barrington town official number?

It is the advertised daily rate in the locked AirROI extract for this town , Airbnb-only, TTM August 2025-July 2026, updated 2026-08-08,. It is not a Selectboard series and not a Department of Revenue table. Do not treat it as every house’s nightly rate. Use your own folio once you have a year. This report uses one locked AirROI pull: Airbnb-only, trailing twelve months August 2025-July 2026, updated 2026-08-08,.

Why is occupancy only 37.4% if August looks strong?

The peak-three months in the same extract are August, October, and July. August is the peak cell at. Occupancy is a twelve-month figure. Quiet winter and mud weeks pull the annual rate down. That is a season story, not proof the town has no guests. Leave neighboring town figures on their own labeled lines when you quote them.

Can I run two Great Barrington STRs if I own two houses?

the matching section above, adopted at Annual Town Meeting in June 2022 and effective January 1, 2023, says an owner may register only one dwelling unit as a short-term rental. If you own two properties, you choose one. Confirm the current text on townofgbma.gov. Do not plan a two-unit GB portfolio in one name. What it has is stricter in a different way: annual registration with the town and with the Massachusetts Department of Revenue; one dwelling unit per owner;.

Is there a numbered permit cap like Woodstock’s 55?

Not in the the matching section above text on the town site. The supply rules are registration, one unit per owner, a 150-day limit when the owner is not on premises, and a ban on corporate-owned units. That is a different constraint than a lottery cap. Read the regulation post in this cluster for the full walk.

What is the registration fee?

The town’s GovOS portal FAQ, checked August 2026, lists a $200 Short-Term Rental registration fee (townofgb.munirevs.com/faq/). the matching section above gives the Selectboard authority to set fees. Confirm the current amount in the portal or with the Selectboard office at before you lock a spreadsheet cell.

Should I use Berkshire County visitor spending as my occupancy forecast?

1Berkshire’s county figures and VisitMA’s $24.2 billion statewide 2024 spending are real, dated, and the wrong geography for a Great Barrington folio. There is no official town visitor-spend line in the sources used here. Say county or state when you quote those tables. Do not Keep “Great Barrington’s $610 million.”. There is no official 2024 “Town of Great Barrington visitor spend” line in the VisitMA statewide report or in 1Berkshire’s county Keep-ups that we are using here.

Is Lenox part of this market extract?

Lenox is a separate CLEAR town on the same 2026-08-14 filter, with its own median ( in that filter , not this cluster). Do not blend Lenox nights into Great Barrington’s median. Stockbridge is another town. Keep the government on every local rule you Keep.

Where do I register?

Annually with the Town of Great Barrington through the Short-Term Rental Registration Hub (townofgbma.gov/377) and with the Massachusetts Department of Revenue. The hub says you must register even for one night per year. Licensed hotels, motels, B&Bs, and lodging houses are treated separately on that page. Hotels, motels, bed and breakfasts, and lodging houses already licensed with the town are told they do not need this STR registration if they advertise on short-term sites.

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