Lanesboro

As of May 2026, Pittsfield, Lenox, Great Barrington have 1,353 active Airbnb and VRBO listings. This represents a 7% decrease from the previous year.

The average Airbnb or VRBO in Lanesboro generates $41K per year. High-performing properties earn $88K/year, while low-performing properties earn $18K/year. The massive performance gap suggests that revenue potential is highly polarized, with top-tier listings capturing a disproportionate share of total market demand despite contracting revenue figures.

Average home prices in Lanesboro vary by property size: 1-bedroom properties cost approximately $194K, 2-bedroom homes average $335K, 3-bedroom properties are around $417K, and 4+ bedroom homes average $511K. These prices reflect median home values across the Pittsfield, Lenox, Great Barrington area.

Airbnb and VRBO can be profitable in Lanesboro, with an average gross yield of 9% across all properties. High-performing properties achieve yields up to 20%, which is considered top for short-term rental investment. This wide yield variance indicates that while the market is consolidating, elite assets maintain strong profitability relative to broader industry benchmarks.

The average occupancy rate for Airbnbs and VRBOs in Lanesboro is 32%. This occupancy level, combined with an average nightly rate of $365, results in a RevPAR (revenue per available room) of $74 per day.

4+ bedroom properties demonstrate the strongest performance in Lanesboro, with an average gross yield of 11% and annual revenue of $64K. These properties balance purchase price ($511K), operating costs, and rental demand most effectively in the Lanesboro market.

Short-term rental regulations vary by jurisdiction in the Lanesboro area. Pittsfield: Moderate. Registration required, annual permit, inspections, local contact mandated. Standard zoning rules apply. Moderate enforcement through complaints. Lenox: Moderate. Registration and permit required, health/safety inspections, occupancy limits enforced. Town actively monitors compliance through complaints and periodic checks. Great Barrington: Lenient. Basic registration with town clerk, minimal restrictions beyond standard lodging rules. Light enforcement, largely complaint-driven with limited proactive monitoring. Always verify current regulations with local authorities and obtain necessary permits before operating a short-term rental.

The Lanesboro Airbnb and VRBO market is currently showing balanced conditions. Supply has declined 7% year-over-year, while RevPAR has decreased 17%. This indicates balanced supply-demand dynamics. The synchronized decline in both supply and revenue points toward a market correction where lower-earning inventory is being removed, stabilizing the competitive landscape.

Launch around April, 2-3 months before peak summer season (July peaks). This pre-peak timing lets you build reviews when competition is 11% lower than peak months. Avoid launching during peak season when established listings dominate, or slow months (May-March) when gaining traction is harder.

The most common amenities in Lanesboro listings include: Kitchen (97%), Air Conditioning (87%), Tv (80%), Washing Machine (75%), Heating (72%). Amenities that boost revenue the most include Pool, Hot Tub, Washing Machine, with Pool properties earning approximately 55% more ($102K/year vs $66K/year).

Monthly estimated revenue per listing in Lanesboro over the last 12 months: May: $2K, June: $2K, July: $3K, August: $3K, September: $2K, October: $3K, November: $2K, December: $3K, January: $2K, February: $2K, March: $1K, April: $2K. These figures are based on RevPAR (revenue per available room) multiplied by the number of days in each month.

The overall average nightly rate in Lanesboro is $365, up 9% year-over-year. By property size: 1-bedroom properties average $199/night, 2-bedroom properties average $262/night, 3-bedroom properties average $362/night, 4+ bedroom properties average $629/night. Rates peak in December and are lowest in May.

Guests in Lanesboro book an average of 38 days in advance, down 23% from last year. By property size: 1-bedroom: 33 days, 2-bedroom: 36 days, 3-bedroom: 39 days, 4+ bedroom: 46 days. Larger properties tend to have longer booking windows as guests plan group trips further ahead.

Over the past year, the Lanesboro Airbnb and VRBO market has seen the following changes: supply declined 7%, revenue per listing decreased 17%, occupancy fell 8%, average nightly rates increased 9%, and lead time decreased 23%. Reduced lead times combined with higher rates suggest a shift toward more spontaneous, value-sensitive booking behavior.

In Lanesboro, Saturday sees the highest booking demand while Tuesday has the lowest. Nightly rates peak on Friday and are lowest on Tuesday. Weekends show 61% higher occupancy than weekdays.