Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Westport, Massachusetts
In Westport, Massachusetts, guests can find a variety of Airbnb accommodations that cater to diverse preferences and needs. The area offers charming coastal cottages and beach houses, perfect for those looking to enjoy the scenic beauty of the Atlantic Ocean and nearby beaches. For a more rustic experience, visitors can opt for cozy farmhouses or country homes, often surrounded by lush landscapes and offering a peaceful retreat. Additionally, there are modern apartments and guest suites available, providing comfortable and convenient options for travelers seeking proximity to local attractions and amenities. Whether guests are looking for a serene getaway or a base to explore the region, Westport's Airbnb options provide a range of choices to suit different tastes and budgets.
As of the latest information, Westport, 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 with the Massachusetts Department of Revenue and collect a state lodging tax of 5.7%. Additionally, there is a local option for cities and towns to impose an additional community impact fee of up to 6% for professionally managed units, though Westport has not enacted such a fee. Hosts must also adhere to general health and safety standards and ensure their properties meet any applicable building codes and occupancy limits.
Managing an Airbnb in Westport, Massachusetts, involves several key tasks to ensure a successful operation. Hosts need to focus on maintaining the property to meet guest expectations, which includes regular cleaning, maintenance, and restocking of essential supplies. 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 obtaining necessary permits or licenses is essential to avoid legal issues. Implementing a system for managing reviews and feedback can help improve guest satisfaction and enhance the property's reputation.
Weston, Vermont, is a charming and picturesque town that offers a quintessential New England experience, making it an ideal location for an Airbnb stay. The best areas to consider are those close to the village center, where you can enjoy the historic charm and easy access to local attractions. Staying near the Weston Playhouse Theatre Company is perfect for theater enthusiasts, while those looking to explore the outdoors might prefer accommodations near the Green Mountain National Forest for hiking and nature activities. Additionally, being close to the Vermont Country Store allows for a delightful shopping experience. Overall, choosing a location that offers a blend of cultural, historical, and natural attractions will enhance your stay in this idyllic Vermont town.
Westport, Massachusetts, offers a promising Airbnb market for investors due to its charming coastal location and appeal as a serene getaway. The town's proximity to popular tourist destinations like Horseneck Beach State Reservation and its picturesque rural landscapes make it attractive to visitors seeking a blend of beach and countryside experiences. Additionally, Westport's rich history, local wineries, and vibrant arts scene contribute to its allure as a vacation spot. The relatively low density of short-term rentals compared to more urban areas can provide less competition and potentially higher occupancy rates. Investors can capitalize on the demand for unique, tranquil accommodations by offering well-maintained properties that highlight the area's natural beauty and local attractions.
As of the latest data, the average Airbnb revenue in Westport, Massachusetts, reflects a modest yet steady income for hosts, driven by the town's appeal as a serene coastal destination. The revenue varies significantly depending on factors such as property type, location, and seasonality, with peak earnings typically occurring during the summer months when tourists flock to the area for its beaches and outdoor activities. Hosts with properties offering unique amenities or proximity to local attractions tend to see higher revenues. Overall, while not as high as in major urban centers, the Airbnb market in Westport provides a reliable supplementary income for property owners capitalizing on the town's charm and tourist appeal.
Westport, Massachusetts, experiences a relatively high occupancy rate for Airbnbs, particularly during the summer months, as it is a popular destination for beachgoers and those seeking a coastal retreat. The town's proximity to Horseneck Beach State Reservation and its charming rural landscape attract visitors looking for a mix of relaxation and outdoor activities. Occupancy rates tend to peak from June through August, driven by the influx of tourists and vacationers. In contrast, the off-peak months, particularly from late fall through early spring, see a decline in occupancy as the cooler weather and reduced tourist activity lead to fewer bookings. However, some visitors are drawn year-round by the area's wineries, farms, and scenic beauty, which help maintain a moderate level of occupancy even in the quieter months.
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.