Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Oak Bluffs, Massachusetts
Oak Bluffs, Massachusetts, offers a diverse range of Airbnb accommodations that cater to various preferences and budgets. Visitors can choose from charming Victorian cottages, which reflect the town's historic character, to modern beachfront homes that provide stunning ocean views. Many properties are equipped with amenities such as full kitchens, outdoor spaces, and proximity to local attractions like the iconic Flying Horses Carousel and Inkwell Beach. For those seeking a more unique experience, there are also cozy guest suites and rustic cabins nestled in quieter, wooded areas. Whether guests are looking for a romantic getaway, a family vacation spot, or a solo retreat, Oak Bluffs provides a variety of options to suit different needs and enhance the Martha's Vineyard experience.
In Oak Bluffs, Massachusetts, short-term rentals, including those listed on platforms like Airbnb, are subject to specific regulations. Property owners must register their short-term rental properties with the town and comply with local zoning laws, which may restrict the number of days a property can be rented out annually. Additionally, short-term rentals are subject to the Massachusetts state lodging tax, which includes a 5.7% state tax, a local option tax of up to 6%, and a 2.75% Cape Cod and Islands Water Protection Fund tax. Hosts are responsible for collecting and remitting these taxes to the appropriate authorities. Compliance with health and safety standards, such as smoke detectors and carbon monoxide alarms, is also required to ensure guest safety.
Managing an Airbnb in Oak Bluffs, Massachusetts, involves several key tasks to ensure a successful operation. Hosts need to focus on maintaining the property to meet high cleanliness and safety standards, which includes regular cleaning, restocking essentials, and addressing any maintenance issues promptly. Effective communication with guests is crucial, from providing clear check-in instructions to being responsive to inquiries and concerns. Marketing the property through appealing listings and competitive pricing strategies is essential to attract bookings, especially during peak tourist seasons. Additionally, staying informed about local regulations and compliance requirements is necessary to avoid any legal issues. Finally, fostering positive guest experiences through personalized touches and local recommendations can lead to favorable reviews and repeat bookings.
Oak Bluffs, Massachusetts, is a charming town on Martha's Vineyard known for its vibrant atmosphere and picturesque scenery. The best areas to stay in an Airbnb include the historic Cottage City neighborhood, famous for its colorful gingerbread cottages and close proximity to the bustling Circuit Avenue, where you'll find an array of shops, restaurants, and entertainment options. Another great area is East Chop, offering stunning views of the ocean and a more tranquil setting, perfect for those looking to relax and enjoy the natural beauty of the island. Staying near the Oak Bluffs Harbor is also ideal, providing easy access to the ferry, waterfront dining, and beautiful beaches. Each of these areas offers a unique experience, making Oak Bluffs a delightful destination for any traveler.
Oak Bluffs, Massachusetts, located on the picturesque island of Martha's Vineyard, is a highly attractive market for Airbnb investment due to its unique blend of charming Victorian architecture, vibrant arts scene, and beautiful beaches. The town's popularity as a summer destination ensures a steady influx of tourists, particularly during peak season, which can lead to high occupancy rates and premium rental prices. The area's rich cultural heritage, including the famous gingerbread cottages and the historic Flying Horses Carousel, adds to its appeal, drawing visitors interested in both relaxation and exploration. Additionally, Oak Bluffs' proximity to other popular island attractions and its well-connected ferry services make it a convenient and desirable location for short-term rentals. Investors can capitalize on the strong demand for vacation rentals by offering well-maintained, unique properties that cater to the diverse needs of travelers seeking a quintessential New England island experience.
Oak Bluffs, Massachusetts, a popular vacation destination on Martha's Vineyard, typically sees a significant fluctuation in Airbnb revenue due to its seasonal tourism. During the peak summer months, when the island attracts a large number of visitors, Airbnb hosts in Oak Bluffs can expect higher average revenues, often benefiting from the increased demand for short-term rentals. This period usually results in higher occupancy rates and premium pricing, contributing to substantial earnings. Conversely, during the off-season, the average revenue tends to decrease as the tourist influx diminishes, leading to lower occupancy and reduced nightly rates. Overall, the average Airbnb revenue in Oak Bluffs is heavily influenced by the seasonal nature of tourism in the area, with summer months being the most lucrative for hosts.
Oak Bluffs, Massachusetts, located on the island of Martha's Vineyard, experiences significant seasonality in its Airbnb occupancy rates, primarily driven by its appeal as a summer vacation destination. During the peak summer months, particularly from June to August, occupancy rates are notably high as tourists flock to the area for its beaches, cultural events, and scenic beauty. This period often sees occupancy rates reaching near full capacity, with many properties booked well in advance. In contrast, the off-season months, especially from late fall through early spring, witness a substantial drop in occupancy as the island becomes quieter and less frequented by tourists. This seasonal fluctuation is typical for coastal vacation spots in New England, where the summer months are the primary draw for visitors.
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.