Great Barrington, Massachusetts Short-Term Rental Market
Great Barrington STRs averaged $256/night at 38.2% occupancy in April 2026 across roughly 1,885 active listings.
Quick Answer: Great Barrington, Massachusetts is an active short-term rental market. average occupancy in the The Berkshire Mtns market area is 55%. average monthly revenue in the The Berkshire Mtns market area is $4,060. average daily rate in the The Berkshire Mtns market area is $335. 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
Great Barrington anchors short-term rental activity across the southern Berkshires, drawing weekenders and second-home visitors from the New York City and Boston metros. The market held approximately 1,885 active listings as of the latest snapshot, with entire-place units making up the dominant share at 1,692 listings, private rooms accounting for 192, and just one shared-room listing. Bedroom distribution is fairly even across one through three bedrooms (492, 418, and 493 listings respectively), with four-bedroom (312) and five-plus-bedroom (167) properties rounding out the supply.
For April 2026, the market posted an average daily rate of $255.69 and an occupancy rate of 38.2%, producing a RevPAR of $97.62. Year over year, occupancy declined 4.7 percentage points while ADR rose 6.2%, and average monthly revenue per listing increased 2.9% to $2,504. On the channel side, 920 listings appear exclusively on Airbnb, 188 exclusively on VRBO, and 777 are cross-listed on both platforms. The market’s overall investability score of 75.8 out of 100, combined with a revenue-growth score of 82.7, signals meaningful upside potential despite the April occupancy softness.
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
Great Barrington enacted its Short-Term Rental Bylaw (Article 25) at the June 2022 Annual Town Meeting, with mandatory registration taking effect January 1, 2023. All STRs must register annually with the Town via the MuniRevs portal and separately with the Massachusetts Department of Revenue, even for single-night rentals. The annual registration fee is $200.
A notable constraint is the one-unit-per-owner cap: each owner may register only one dwelling unit as an STR. Rental nights are capped at 150 per calendar year unless the owner is residing in a unit on the same property during the rental, in which case no night cap applies. There is no owner-occupancy or primary-residence requirement beyond this conditional cap structure. STRs are prohibited in deed-restricted affordable housing units and in properties with outstanding code or bylaw violations.
The tax burden is significant. Guests pay the 5.7% Massachusetts state room occupancy excise plus the Town’s 6% local option tax, putting the combined lodging tax at approximately 11.7%. Operational rules prohibit amplified-music events, large tents requiring permits, and advertising signs, and restrict noise to between 8 a.m. and 8 p.m. Enforcement severity is rated moderate with escalating fines beginning at $100.
Market Comparison
The national short-term rental median occupancy is approximately 55%, making Great Barrington’s April 2026 rate of 38.2% below the national benchmark for that month. The all-listing ADR of $255.69 exceeds the national median of approximately $220, reflecting the Berkshires’ premium as an established cultural tourism destination with limited housing supply. RevPAR of $97.62 is moderate given the high ADR, pointing to occupancy as the main lever for improvement.
Among local operators, Evolve leads the market with 60 listings and 2,327 reviews at an average rating of 4.74. Evergreen Home ranks second with 31 listings and 2,154 reviews at 4.96, while Mergo Realty holds 29 listings with 1,618 reviews at 4.82. The top five property managers collectively operate 165 listings, or approximately 8.8% of the roughly 1,885-listing market. The market’s overall score of 61.3 out of 100 reflects strengths in investability (75.8) and revenue growth (82.7), partially offset by moderate rental demand (50.5) and meaningful seasonality (60.4).
Frequently Asked Questions About Great Barrington, Massachusetts
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