Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Gloucester, Massachusetts
In Gloucester, Massachusetts, guests can find a diverse range of Airbnb accommodations that cater to various preferences and budgets. Visitors can choose from charming seaside cottages that offer stunning views of the Atlantic Ocean, perfect for those seeking a tranquil coastal retreat. There are also historic homes and quaint bed-and-breakfasts that provide a cozy and authentic New England experience. For larger groups or families, spacious beach houses with modern amenities are available, offering ample space and comfort. Additionally, travelers can find unique stays such as converted barns or artist lofts that provide a distinctive and creative atmosphere. Whether seeking a romantic getaway, a family vacation, or a solo adventure, Gloucester's Airbnb options offer something for everyone, all while being conveniently located near the city's picturesque beaches, vibrant arts scene, and renowned seafood restaurants.
In Gloucester, Massachusetts, short-term rentals, including those listed on platforms like Airbnb, are subject to specific regulations. Hosts are required to register their properties with the city and obtain a short-term rental certificate. The city imposes a local excise tax on short-term rentals, which is in addition to the state’s room occupancy tax. This means that hosts must collect and remit both state and local taxes from their guests. Additionally, there are zoning regulations that dictate where short-term rentals can operate, often distinguishing between owner-occupied and non-owner-occupied properties. Compliance with health and safety standards is also mandatory, ensuring that all short-term rental properties meet the necessary requirements for occupancy.
Managing an Airbnb in Gloucester, 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, restocking essentials, and ensuring all amenities are in working order. Given Gloucester's coastal location, it's important to emphasize local attractions in the listing, such as beaches, seafood restaurants, and cultural sites like the Cape Ann Museum. Effective communication with guests is crucial, from promptly responding to inquiries and booking requests to providing detailed check-in instructions and local recommendations. Additionally, hosts should stay informed about local regulations and compliance requirements for short-term rentals, including any necessary permits or taxes. Seasonal adjustments may also be necessary, such as preparing for increased demand during summer months and ensuring the property is winterized during colder seasons.
Gloucester, Massachusetts, offers several charming areas for an Airbnb stay, each with its unique appeal. The downtown area is ideal for those who want to be in the heart of the action, with easy access to local shops, restaurants, and the vibrant arts scene. Staying near Good Harbor Beach provides a more relaxed atmosphere, perfect for beach lovers and families looking to enjoy the sun and surf. The Rocky Neck Art Colony area is another excellent choice, offering a blend of artistic flair and scenic beauty, with galleries and stunning ocean views. Lastly, East Gloucester offers a quieter, more residential feel, with proximity to scenic drives and the iconic Eastern Point Lighthouse. Each of these areas provides a distinct experience, catering to different preferences and ensuring a memorable stay in Gloucester.
Gloucester, Massachusetts, presents a promising Airbnb investment opportunity due to its rich maritime history, scenic coastal views, and vibrant cultural scene. As a popular tourist destination, especially during the summer months, Gloucester attracts visitors with its beautiful beaches, whale-watching tours, and the iconic Fishermen's Memorial. The city's proximity to Boston also makes it an appealing getaway for urban dwellers seeking a coastal retreat. Investing in Airbnb properties in neighborhoods close to the waterfront or near attractions like Rocky Neck Art Colony and Good Harbor Beach can yield high occupancy rates. Additionally, Gloucester's local events, such as the annual Schooner Festival and St. Peter's Fiesta, draw significant crowds, further enhancing the potential for lucrative short-term rental returns.
As of the latest data, the average Airbnb revenue in Gloucester, Massachusetts, reflects a dynamic market influenced by its coastal charm and tourist appeal. Hosts in Gloucester typically see varying revenue depending on the season, with peak earnings during the summer months when tourism is at its highest due to the city's beaches, historic sites, and cultural events. On average, hosts can expect monthly revenues ranging from moderate to high, contingent on factors such as property location, amenities offered, and occupancy rates. The city's proximity to Boston also contributes to its attractiveness as a short-term rental destination, further impacting revenue potential positively. Overall, Gloucester's Airbnb market offers promising opportunities for hosts, particularly those who can capitalize on the seasonal influx of visitors.
Gloucester, Massachusetts, experiences a notable fluctuation in Airbnb occupancy rates due to its strong seasonality, primarily driven by its coastal location and appeal as a summer destination. During the peak summer months, from June to August, occupancy rates tend to be high as tourists flock to the area to enjoy its beaches, maritime activities, and cultural events. This period often sees occupancy rates reaching upwards of 80-90%. In contrast, the off-peak months, particularly from November to March, witness a significant drop in occupancy, often falling below 50%, as the colder weather and reduced tourist activities lead to decreased demand. The shoulder seasons of spring and fall offer moderate occupancy rates, attracting visitors interested in a quieter experience and the region's natural beauty.
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.