Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Lee, Massachusetts
In Lee, Massachusetts, guests can find a diverse range of Airbnb accommodations that cater to various preferences and budgets. The area offers charming historic homes and cozy cottages that reflect the quintessential New England charm, often featuring rustic decor and inviting fireplaces. For those seeking a more luxurious experience, there are elegant estates and modern villas with expansive grounds and upscale amenities. Additionally, visitors can opt for unique stays such as converted barns or artistically designed lofts that provide a distinctive and memorable experience. Many of these properties are nestled in picturesque settings, offering stunning views of the Berkshires and easy access to outdoor activities, making them ideal for both relaxation and adventure.
In Lee, Massachusetts, there are currently no specific local laws governing the operation of Airbnbs or short-term rentals. However, hosts must comply with state regulations, which require short-term rental operators to register with the Massachusetts Department of Revenue. They must also collect and remit a state lodging tax of 5.7%, along with a local option tax of up to 6% that Lee has adopted. Additionally, a 2.75% community impact fee may apply if the property is a professionally managed unit. Hosts should ensure compliance with any applicable health and safety standards and consider obtaining appropriate insurance coverage.
Managing an Airbnb in Lee, Massachusetts, involves several key tasks to ensure a smooth operation and positive guest experience. Hosts need to maintain the property by ensuring it is clean, well-stocked, and in good repair, which may involve coordinating with local cleaning and maintenance services. Effective communication with guests is crucial, from promptly responding to inquiries and booking requests to providing detailed check-in instructions and local recommendations. Pricing strategies should be regularly reviewed and adjusted based on seasonal demand and local events to maximize occupancy and revenue. Additionally, compliance with local regulations and tax requirements is essential, which may include obtaining necessary permits and remitting occupancy taxes. Finally, managing guest reviews and feedback is important for maintaining a high rating and attracting future bookings.
Lee, Massachusetts, nestled in the heart of the Berkshires, offers several charming areas ideal for an Airbnb stay. The downtown area is a great choice, providing easy access to quaint shops, local eateries, and cultural attractions like the Lee Library and the historic Congregational Church. Staying near Laurel Lake offers a serene experience with opportunities for swimming, kayaking, and picnicking. For those seeking a more rural retreat, the outskirts of Lee provide picturesque landscapes and proximity to hiking trails in the Beartown State Forest. Each area offers a unique blend of small-town charm and natural beauty, making Lee a delightful destination for visitors.
Lee, Massachusetts, located in the heart of the Berkshires, presents a promising Airbnb investment opportunity due to its appeal as a year-round tourist destination. The town's proximity to popular attractions such as Tanglewood, the Norman Rockwell Museum, and the scenic Appalachian Trail makes it a magnet for visitors seeking cultural, historical, and outdoor experiences. The demand for short-term rentals is bolstered by the area's vibrant arts scene, seasonal festivals, and picturesque landscapes, attracting a diverse range of guests from families to solo travelers. Additionally, Lee's charming small-town atmosphere, combined with its accessibility to larger cities like Boston and New York, enhances its attractiveness as a convenient and relaxing getaway. Investors can capitalize on the steady influx of tourists by offering unique and comfortable accommodations that cater to the diverse needs of visitors exploring the Berkshires.
As of the latest data, the average Airbnb revenue in Lee, Massachusetts, reflects a modest yet steady income for hosts, driven by the town's appeal as a gateway to the Berkshires. Lee's proximity to popular attractions such as Tanglewood, the Norman Rockwell Museum, and various outdoor activities makes it a desirable location for short-term rentals. Hosts in Lee typically see higher occupancy rates during peak tourist seasons, particularly in the summer and fall, when visitors flock to the area for its cultural events and scenic beauty. The average revenue can vary significantly depending on factors such as property size, amenities, and location within the town, but overall, Lee offers a competitive market for Airbnb hosts looking to capitalize on the region's tourism.
Lee, Massachusetts, located in the heart of the Berkshires, experiences a fluctuating Airbnb occupancy rate that is heavily influenced by its seasonal attractions. The town sees its highest occupancy rates during the summer and fall months, particularly from June to October, when tourists flock to the area for outdoor activities, cultural events, and the vibrant fall foliage. During these peak months, occupancy rates can soar, often reaching above 70-80%. Conversely, the winter months, while still attracting visitors for nearby skiing and holiday events, tend to see a dip in occupancy, with rates typically ranging from 40-60%. The spring season also experiences moderate occupancy as the weather begins to warm and the area's natural beauty starts to bloom. Overall, Lee's Airbnb market is characterized by its strong seasonal demand, driven by the region's appeal as a year-round destination for nature and culture enthusiasts.
Why Choose Checkmate Rentals?
![]() | Other Property Managers | |
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Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
Checkmate Rentals

Attract Guests
List on top booking sites
Optimize listings for SEO
Feature show-stopping photos
Competitive, dynamic pricing
Mangage Operations
Tailored pricing algorithms
24/7 guest service
Reliable, professional cleaning
Restocking & inventory management
Maintenance coordination


Host Care
Unlimited owner stays
Flexible contract options
East to use host portal
Set it and forget it billing
Exclusive insurance discounts via our partner network
Get in touch with us.

Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.

Ready to make the jump?
Let's get started! Schedule a call today to learn more about Checkmate Rentals.