Great Barrington, Massachusetts Short-Term Rental Market
Great Barrington caps non-resident STRs at 150 nights, with September 2026 ADR $312, occupancy 43.3%, revenue $3,673.
Quick Answer: Great Barrington, Massachusetts is an active short-term rental market. average occupancy in the The Berkshire Mtns market area is 43%. average monthly revenue in the The Berkshire Mtns market area is $3,673. average daily rate in the The Berkshire Mtns market area is $312. the top operator in the The Berkshire Mtns market area is Evolve with 60 listings. market score is 61/100 (grade C).
Market data reflects the The Berkshire Mtns regional market, which includes Great Barrington. Regulations, taxes, and permit details below are specific to Great Barrington.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
This profile uses data through September 2026 for the Great Barrington short-term rental market in the southern Berkshires of western Massachusetts. In September 2026 the average daily rate across all listings was $312, occupancy was 43.3%, and average monthly revenue per listing was $3,673. Compared with a year earlier, occupancy is up 10.7%, ADR is up 4.7%, and revenue is up 6.9%. Great Barrington is the commercial and dining hub of the southern Berkshires, a four-season cultural tourism region that draws weekenders and second-home owners from the New York City and Boston metros, especially during Tanglewood season in summer and peak fall foliage. The Great Barrington area STR market tracks 1,885 listings. Entire places make up 1,692 of them (89.8%), with 192 private rooms and 1 shared room. By bedroom count the area has 492 one-bedroom listings, 418 two-bedroom, 493 three-bedroom, 312 four-bedroom, and 167 five-bedroom listings, so supply is spread fairly evenly from small units to large houses. By channel, 920 listings are on Airbnb only, 188 are on Vrbo only, and 777 are on both platforms. The town has a population of 7,202, and the local rules matter for investors: STRs are permitted, annual registration is required, and owners who do not live on the premises are limited to 150 rental nights per year. Over the longer view, average monthly revenue per listing rose from $2,288 in 2019 to $3,700 in 2025, and the 2026 figure stands at $3,868 across the nine months reported so far.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 37% |
| Feb | 47% |
| Mar | 34% |
| Apr | 43% |
| May | 49% |
| Jun | 56% |
| Jul | 67% |
| Aug | 67% |
| Sep | 44% |
| Oct | 51% |
| Nov | 38% |
| Dec | 44% |
Month-by-month nightly rates and revenue figures for Great Barrington are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in The Berkshire Mtns market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the The Berkshire Mtns market as a whole, which includes Great Barrington, so these counts are not Great Barrington-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Evolve | 60 | 2,327 | ★ 4.74 |
| 2 | Evergreen Home | 31 | 2,154 | ★ 4.96 |
| 3 | Mergo Realty | 29 | 1,618 | ★ 4.82 |
| 4 | Berkshire Vacation Rental | 23 | 845 | ★ 4.86 |
| 5 | Berkshire Rental Properties | 22 | 481 | ★ 4.95 |
What Kind of STR Should I Buy in Great Barrington?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Great Barrington are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 48.8% |
| vrbo | 10% |
| both | 41.2% |
Home Value Trends (Great Barrington)
Typical home values, median sale prices, and the 10-year price trend for Great Barrington are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Great Barrington — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Short-term rentals are permitted in Great Barrington under Article 25, the Short-Term Rental Bylaw, adopted at the June 6, 2022 Annual Town Meeting and effective January 1, 2023. An STR is any rental of 30 days or less. Every unit must be registered annually with the town through the MuniRevs portal and also with the Massachusetts Department of Revenue. The town registration fee is $200 per year. An owner may register only one dwelling unit as an STR. Rental nights are capped at 150 per year unless the owner lives in a unit on the premises during the rental, in which case there is no cap. There is no general primary residence or owner occupancy requirement. Zoning allows STRs by right in residential dwellings, with owners able to rent up to two bedrooms or an entire secondary unit. Hotels, motels, and lodging houses are excluded, and STRs are prohibited in deed-restricted affordable housing units and on properties with outstanding building, fire, health, or bylaw violations. Units need working smoke and CO detectors and a fire extinguisher. Amplified music events, permitted tents, and advertising signs are prohibited. Guests pay the 5.7% state room occupancy excise plus the 6% local option tax, and the state allows a further 3% community impact fee. Enforcement is rated moderate, with escalating fines of $100, $200, and $300 for successive offenses. Local debate about tightening the rules to ease housing pressure was ongoing as of 2024 and 2025, so owners should confirm current requirements with the town.
Market Comparison
Great Barrington earns $312 ADR at 43.3% occupancy in September 2026, and even the August peak reaches only 67.3% occupancy, so the market depends on seasonal rate and demand concentration. Revenue growth is solid, with monthly revenue up 6.9% year over year. The Great Barrington area STR market is dominated by independent hosts alongside a few larger operators. The top five property managers by listing count are Evolve with 60 listings, Evergreen Home with 31, Mergo Realty with 29, Berkshire Vacation Rental with 23, and Berkshire Rental Properties with 22. Together they manage 165 of the 1,885 tracked listings, about 8.8%, so the field is fragmented and local operators remain competitive. Guest ratings for these managers range from 4.74 to 4.96, which sets a high service bar for new entrants. The market score for regulation is 71.4 and for investability is 75.8, and revenue growth scores 82.7, while rental demand scores 50.5.
Frequently Asked Questions About Great Barrington, Massachusetts
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