Airbnb and Short-Term Rentals in the Berkshires: What Homeowners Should Know Before Listing
The Berkshires have always been a destination—a place where New Yorkers escape for culture, nature, and peace. From the world-class performances at Tanglewood to hiking trails that wind through pristine forests, from cozy fireside retreats in winter to lakeside summer getaways, the region offers something for every traveler.
And increasingly, homeowners are cashing in on that appeal.
If you own a home in Great Barrington, Lenox, Stockbridge, Williamstown, or anywhere else in western Massachusetts, you've probably wondered: Could my property become a profitable short-term rental? The answer is yes—but success requires strategy, not just good intentions.
This guide will walk you through what you need to know before listing on Airbnb or VRBO.
The Berkshires Vacation Rental Market: Real Opportunity
The Berkshires aren't just a seasonal destination anymore. While summer remains peak season—driven by Tanglewood's concert series, galleries, and outdoor activities—the market now spans all four seasons.
Summer (June–August): Peak season. Families book months in advance for lakefront properties, estates with pools, and charming village cottages. Nightly rates typically range from $250–$400+, with premium properties commanding significantly more.
Fall (September–October): Extended peak. Leaf-peepers fill the region. Foliage-view homes and properties near hiking access see strong demand at $200–$350/night.
Winter (November–February): Often overlooked by new hosts—but a hidden opportunity. The region draws holiday travelers, wellness seekers, and adventure guests year-round. Fireplaces, hot tubs, and cozy interiors become premium amenities. Rates hold steady at $150–$250/night.
Spring (March–May): Transitional season with moderate demand and flexible pricing. Rates typically $120–$200/night.
The Real Numbers: Professional managers report average occupancy rates of 50–75% year-round in the Berkshires, with successful properties earning $60,000–$150,000+ annually, depending on size, location, and amenities.
The key difference? Professionally managed properties earn 30–50% more than self-managed listings because they optimize pricing, maintain superior guest experiences, and command premium rates.
What Guests Actually Want in the Berkshires
Understanding your market is half the battle. Berkshires guests aren't looking for cookie-cutter rentals—they want experiences.
Design & Aesthetic: Guests in the Berkshires are design-conscious. They expect curated interiors, thoughtful staging, and authenticity that reflects the region's character. A renovated farmhouse with clean lines and natural materials outperforms a dated rental every time. High-quality photography isn't optional—it's essential.
Outdoor Space: Decks, patios, fire pits, and lake access are major booking drivers. Properties with outdoor entertaining space see 20–30% higher booking rates and command premium pricing.
Amenities That Matter:
Fireplaces (creates warmth and ambiance)
Hot tubs (year-round luxury appeal)
Full kitchens (families planning week-long stays)
Washer/dryer (non-negotiable for most guests)
WiFi & streaming services (remote workers are now year-round renters)
Pet-friendly policies (the Berkshires draw dog-loving crowds)
Proximity & Location: Properties within 10 minutes of Tanglewood, Great Barrington's main drag, or hiking trailheads see 40–60% higher booking rates. Location data matters—guests search by experience first, property second.
Before You List: A Quick Checklist
Before launching your rental, make sure you've addressed the basics:
✓ Check local requirements — Different towns have different rules about short-term rentals. A quick call to your town's assessor or planning department ensures you're clear to proceed.
✓ Verify your insurance — Standard homeowner's policies don't cover short-term rentals. You'll need a specialized vacation rental policy.
✓ Understand tax obligations — Income from rentals is taxable. Keep records of bookings and expenses.
✓ Set clear house rules — Quiet hours, maximum occupancy, guest conduct, pet policies, and parking help prevent issues and protect your property.
This isn't complicated, but it matters. A 20-minute conversation with your town and a call to your insurance agent clears the way to launch confidently.
The Design Advantage: Why Presentation Drives Bookings in the Berkshires
Design-conscious travelers choose the Berkshires specifically for the aesthetic experience. A beautifully staged, professionally photographed home can command 30–50% higher nightly rates than an identical property with poor photos and tired furnishings.
Professional Photography: Invest $500–$1,500 in a professional photoshoot. Poor photos lose bookings—guests literally scroll past listings with dim, cluttered images in favor of bright, spacious, styled ones.
Intentional Staging: Remove personal clutter. Add thoughtful touches—fresh flowers, quality linens, local art, curated book collections. The Berkshires aesthetic is refined but approachable.
Consistency: Your listing copy, photos, and actual property should align. If your description promises "rustic charm," guests should arrive to exactly that—not disappointment.
Unique Selling Points: Highlight what makes your property special. Fireplace with a view? Hot tub overlooking the forest? Access to a private lake? These details drive bookings and justify premium pricing.
Three Smart Moves Before Listing Your Home
1. Stage It Intentionally
Before professional photos, declutter ruthlessly. Add warm lighting, quality linens, and local design touches. A $2,000 staging investment often returns $15,000+ in first-season revenue through higher bookings and rates.
2. Price Competitively from Day One
New hosts often underprice to "build reviews." Instead, price competitively from launch, focusing on high-occupancy seasons. Strategic discounts for early bookings build momentum faster than deep underpricing year-round.
3. Plan for Maintenance Partners
Identify local cleaners, handymen, and service providers now. The difference between a 4.8-star property and a 4.0-star property often comes down to cleaning quality and responsive maintenance. Build relationships before you need them.
Why Professional Management Matters (Especially Here)
The Berkshires market rewards expertise. Pricing, guest communication, and operational management are critical to success.
Here's what professional management delivers:
Dynamic Pricing: Rates adjust based on demand, local events, and seasonality. Professionals know when to charge $400/night (Tanglewood opening weekend) versus $120/night (slow Tuesday in March). Self-managed hosts often leave thousands on the table.
24/7 Guest Support: Someone answers when the WiFi goes down at 11 PM. This responsiveness drives 5-star reviews and repeat bookings.
Marketing Optimization: Professional photos, SEO-optimized listings, and strategic positioning ensure your property ranks high in search and attracts qualified guests.
Vendor Network: Established relationships with cleaners and contractors mean faster turnarounds and better pricing. You benefit from their buying power and local expertise.
Hands-On Strategy: Not a cookie-cutter approach—each property is different, and management should reflect that.
Getting Started: Your Next Steps
Ready to turn your Berkshires home into a profitable rental?
Start with a reality check: Talk to someone who knows the local market. Understand your property's actual potential, not just your hopes.
At Haus Vacation Rentals, we've expanded into the Berkshires because we saw the opportunity—and because we know what it takes to succeed here. We started in the Hudson Valley, managing properties with the same regional expertise and hands-on approach that drives results.
We'll analyze your specific property and provide:
Custom revenue projection based on comparable properties
Competitive market analysis for your area and season
Listing optimization recommendations to maximize bookings
Honest insight on what your property can realistically earn
No obligation. No pressure. Just honest perspective from people who've built a business on helping homeowners succeed.
Text or call (845) 262-0482 to speak with a real Berkshires and Hudson Valley expert—not a call center. Or email hello@str.haus to schedule a free consultation.
The Berkshires deserve hosts who understand the market, respect the guests, and treat their properties with care.
Let's make sure yours is one of them.
Haus Vacation Rentals
Local Expertise. Institutional Results. Personal Service.
(845) 262-0482 | hello@str.haus | www.str.haus
