Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Chilmark, Massachusetts
Chilmark, Massachusetts, offers a variety of Airbnb accommodations that cater to diverse preferences, providing guests with a quintessential New England experience. Visitors can choose from charming cottages and rustic cabins that exude a cozy, countryside vibe, often nestled amidst the scenic landscapes of Martha's Vineyard. For those seeking a more luxurious stay, there are elegant beachfront homes and modern villas offering stunning ocean views and upscale amenities. Additionally, guests can find unique stays such as historic farmhouses and artistically designed retreats that reflect the area's rich cultural heritage. Whether looking for a peaceful rural escape or a lavish coastal getaway, Chilmark's Airbnb options provide a perfect base for exploring the island's natural beauty and local attractions.
As of the latest information, Chilmark, Massachusetts, does not have specific local laws governing short-term rentals like Airbnb. However, hosts must comply with Massachusetts state regulations, which require short-term rental operators to register their properties with the state and collect a 5.7% state room occupancy excise tax. Additionally, there is a local option for towns to impose an additional community impact fee of up to 3% on short-term rentals, though it is unclear if Chilmark has implemented this. Hosts must also adhere to general health and safety standards and ensure their properties are properly insured.
Managing an Airbnb in Chilmark, Massachusetts, involves several key tasks to ensure a smooth operation and a positive guest experience. Hosts need to focus on maintaining the property, which includes regular cleaning, landscaping, and addressing any maintenance issues promptly, given the town's rural and coastal environment. Effective communication with guests is crucial, from the initial booking inquiries to providing detailed check-in instructions and being responsive to any questions or concerns during their stay. Additionally, managing bookings and pricing strategies is essential to maximize occupancy and revenue, taking into account the seasonal nature of tourism in Martha's Vineyard. Compliance with local regulations and obtaining necessary permits is also important to operate legally and avoid fines. Lastly, creating a welcoming atmosphere with personalized touches and local recommendations can enhance guest satisfaction and encourage positive reviews.
Chilmark, Massachusetts, offers a serene and picturesque setting for an Airbnb stay, with several appealing areas to consider. Menemsha is a charming fishing village known for its stunning sunsets, fresh seafood, and quaint harbor views, making it ideal for those seeking a quintessential New England coastal experience. For a more secluded and nature-focused retreat, consider staying near Lucy Vincent Beach or Squibnocket Beach, both offering beautiful landscapes and opportunities for beachcombing and relaxation. The central area of Chilmark provides easy access to the town's cultural attractions, such as the Chilmark General Store and the Chilmark Community Center, while still being close to hiking trails and scenic vistas. Each of these areas provides a unique blend of tranquility and natural beauty, perfect for a peaceful getaway.
Chilmark, Massachusetts, located on the picturesque island of Martha's Vineyard, presents a compelling Airbnb investment opportunity due to its serene landscapes, charming rural character, and appeal as a summer retreat. The town is known for its beautiful beaches, such as Lucy Vincent Beach and Menemsha Beach, which attract tourists seeking a peaceful getaway. The seasonal influx of visitors during the summer months, coupled with limited accommodation options, can drive high occupancy rates and premium rental prices. Additionally, Chilmark's strict zoning laws and limited commercial development help maintain its exclusivity and allure, making it an attractive market for investors looking to capitalize on the demand for unique, high-end vacation rentals. However, potential investors should be mindful of the seasonal nature of the market and the regulatory environment governing short-term rentals on the island.
Chilmark, Massachusetts, a picturesque town on Martha's Vineyard, offers a unique Airbnb market characterized by its seasonal fluctuations and premium pricing. The average Airbnb revenue in Chilmark tends to be higher during the peak summer months, when tourists flock to the island for its beaches, scenic landscapes, and tranquil atmosphere. During this period, hosts can command premium rates, significantly boosting their revenue. However, in the off-season, the demand decreases, leading to lower occupancy rates and reduced income. Overall, the average annual revenue for Airbnb hosts in Chilmark reflects this seasonal variation, with summer months providing the bulk of earnings, while the rest of the year sees a more modest income stream.
Chilmark, Massachusetts, located on Martha's Vineyard, experiences significant seasonality in its Airbnb occupancy rates, primarily driven by its appeal as a summer destination. During the peak summer months, from June to August, occupancy rates are typically high, often reaching near full capacity as tourists flock to the area for its beaches, scenic landscapes, and cultural events. In contrast, the off-season months, particularly from late fall through early spring, see a marked decline in occupancy rates due to the colder weather and reduced tourist activity. This seasonal fluctuation is common in vacation destinations like Chilmark, where the local economy heavily relies on the influx of summer visitors.
Why Choose Checkmate Rentals?
Other Property Managers | ||
---|---|---|
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 |
What you get with Checkmate Rentals
Attract Guests

Listing on all top booking sites
Targeted digital marketing
High-definition photography
Custom copywriting
Manage Details

Dynamic rate-setting technology
Dedicated reservation agents
24/7 guest service
Consistent, professional cleaning
Stocking guest amenities
Payment processing
Take Care of You

Unlimited owner holds
No fixed contracts
Local staff in every market
Inspections and regular maintenance
Guest screening
Optional short-term rental insurance
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.
Direct Bookings
Earn more year after year as guests book their stay directly on our website.
Housekeeping
Make the perfect first impression with wall-to-wall cleanings before guests arrive.
Inspections
Know your property is guest-ready is top-to-bottom inspections after every booking.
Guest Damage Coverage
Save more when you let us cover accidental guest damage coverage up to $3k.
Smart Home Management
We manage your digital locks & noise monitoring tech in your home.
Fast Listings
Get your home fully listed and ready for guests in as little as 3 days.
Automated Touchpoints
Give guests a seamless experience with automated touchpoints from booking to checkout.
Owner Portal
Stay in the loop on your property with our easy-to-use owner portal that lets you check everything you need.
