Monterey, MassachusettsMonterey, Massachusetts

Vacation Rental Management in Monterey, Massachusetts

Discover the best vacation rental management companies in Monterey, Massachusetts to maximize your revenue and create incredible guest experiences

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Monterey, Massachusetts Airbnb Management Overview

Monterey, Massachusetts, is a charming New England town that offers a unique blend of natural beauty, historical charm, and cultural attractions, making it an appealing market for Airbnb hosts. Nestled in the heart of the Berkshires, Monterey is a year-round destination attracting tourists for its scenic landscapes, outdoor activities, and proximity to popular attractions like the Norman Rockwell Museum and Tanglewood Music Center. The town's quaint, rural character and array of charming homes and cottages make it an ideal location for vacation rentals. The market sees a surge during the summer months and fall foliage season, but also maintains steady demand in the winter for nearby skiing and snowboarding activities. The clientele is diverse, ranging from families and nature enthusiasts to culture seekers and history buffs, providing a broad base for potential bookings.

In Monterey, Massachusetts, the Airbnb market experiences significant seasonality, largely influenced by the area's distinct four-season climate and its appeal as a vacation destination. The peak season typically begins in late spring and extends through the summer months, when the weather is warm and the area's outdoor attractions, such as the Monterey Preserves and Lake Garfield, are at their most inviting. During this period, demand for short-term rentals often outpaces supply, leading to higher rental rates and occupancy levels. Conversely, the off-peak season, which spans the colder fall and winter months, sees a decrease in tourism and a corresponding drop in rental demand. However, the fall foliage and winter sports activities do attract a smaller, but steady stream of visitors, helping to offset the seasonal downturn.

In Monterey, Massachusetts, Airbnb hosts must be aware of and comply with a variety of local regulations. As of July 1, 2019, a new law requires all short-term rental operators to register with the Massachusetts Department of Revenue. Additionally, hosts are required to carry liability insurance of not less than $1 million to cover each short-term rental unless such coverage is offered through a hosting platform. There is also a state excise tax on short-term rentals, along with local option taxes that may apply. It's important to note that the town of Monterey has the option to implement a local excise tax of up to 6% on short-term rentals, and a community impact fee of up to 3% on professionally managed properties. Hosts should also be aware of potential zoning regulations that may impact their ability to operate a short-term rental.

Managing Airbnb properties in Monterey, Massachusetts presents unique challenges due to the town's seasonal fluctuations in tourism. The high demand during the summer months requires meticulous scheduling and maintenance to ensure properties are ready for quick turnovers. During the off-peak season, it's crucial to adjust pricing strategies to attract long-term renters. It's also important to build strong relationships with local cleaning services and maintenance professionals to handle any unexpected issues promptly. A key tip for success in this market is to highlight the unique features of the property and the local area in the listing to stand out from the competition.

In Monterey, Massachusetts, the Airbnb market thrives on the area's natural beauty and historical charm. Properties that highlight these features, such as those with views of the Berkshire Hills or proximity to the Monterey General Store, tend to be popular among guests. Amenities that cater to outdoor enthusiasts, such as bike storage, hiking gear, or picnic supplies, can also be a significant draw. Additionally, given the area's reputation for arts and culture, properties that offer a unique or artistic touch, such as local artwork or handcrafted furniture, can stand out in this market. Lastly, with the region's cold winters, amenities like fireplaces, heated floors, or a hot tub can make a property particularly appealing for off-season bookings.

Market Overview

Monterey, Massachusetts, is a charming New England town that offers a unique blend of natural beauty, historical charm, and cultural attractions, making it an appealing market for Airbnb hosts. Nestled in the heart of the Berkshires, Monterey is a year-round destination attracting tourists for its scenic landscapes, outdoor activities, and proximity to popular attractions like the Norman Rockwell Museum and Tanglewood Music Center. The town's quaint, rural character and array of charming homes and cottages make it an ideal location for vacation rentals. The market sees a surge during the summer months and fall foliage season, but also maintains steady demand in the winter for nearby skiing and snowboarding activities. The clientele is diverse, ranging from families and nature enthusiasts to culture seekers and history buffs, providing a broad base for potential bookings.

Airbnb Seasonality

In Monterey, Massachusetts, the Airbnb market experiences significant seasonality, largely influenced by the area's distinct four-season climate and its appeal as a vacation destination. The peak season typically begins in late spring and extends through the summer months, when the weather is warm and the area's outdoor attractions, such as the Monterey Preserves and Lake Garfield, are at their most inviting. During this period, demand for short-term rentals often outpaces supply, leading to higher rental rates and occupancy levels. Conversely, the off-peak season, which spans the colder fall and winter months, sees a decrease in tourism and a corresponding drop in rental demand. However, the fall foliage and winter sports activities do attract a smaller, but steady stream of visitors, helping to offset the seasonal downturn.

Short Term Rental Regulations

In Monterey, Massachusetts, Airbnb hosts must be aware of and comply with a variety of local regulations. As of July 1, 2019, a new law requires all short-term rental operators to register with the Massachusetts Department of Revenue. Additionally, hosts are required to carry liability insurance of not less than $1 million to cover each short-term rental unless such coverage is offered through a hosting platform. There is also a state excise tax on short-term rentals, along with local option taxes that may apply. It's important to note that the town of Monterey has the option to implement a local excise tax of up to 6% on short-term rentals, and a community impact fee of up to 3% on professionally managed properties. Hosts should also be aware of potential zoning regulations that may impact their ability to operate a short-term rental.

Best Practices for Management

Managing Airbnb properties in Monterey, Massachusetts presents unique challenges due to the town's seasonal fluctuations in tourism. The high demand during the summer months requires meticulous scheduling and maintenance to ensure properties are ready for quick turnovers. During the off-peak season, it's crucial to adjust pricing strategies to attract long-term renters. It's also important to build strong relationships with local cleaning services and maintenance professionals to handle any unexpected issues promptly. A key tip for success in this market is to highlight the unique features of the property and the local area in the listing to stand out from the competition.

Locations and Amenities

In Monterey, Massachusetts, the Airbnb market thrives on the area's natural beauty and historical charm. Properties that highlight these features, such as those with views of the Berkshire Hills or proximity to the Monterey General Store, tend to be popular among guests. Amenities that cater to outdoor enthusiasts, such as bike storage, hiking gear, or picnic supplies, can also be a significant draw. Additionally, given the area's reputation for arts and culture, properties that offer a unique or artistic touch, such as local artwork or handcrafted furniture, can stand out in this market. Lastly, with the region's cold winters, amenities like fireplaces, heated floors, or a hot tub can make a property particularly appealing for off-season bookings.

How It Works

Meet with membership

Connect With Local Pros

Summer matches you with top vacation rental managers who know the Monterey, Massachusetts market and can help you maximize your revenue and improve guest experiences. 

We'll make sure to introduce you to Airbnb managers who offer the right services for your needs.

Get Onboarded

Seamless Onboarding

Your manager can handle everything—from listing setup and pricing optimization to guest communication and maintenance.

They’ll take care of professional photography, lockbox installation, profile setup, and everything you need to get your Monterey, Massachusetts property guest-ready.

Collect Revenue

Sit Back And Earn

With the right vacation rental property manager, your home is in good hands.

They'll handle the bookings, guests, pricing updates, and day-to-day operations while you enjoy stress-free earnings and more time for what matters most.

Who We Trust

What makes our partners stand out from other short-term rental property managers in Monterey, Massachusetts

Access to the Summer Network

Personalized Support

Each home and host is different. The best property managers work with you to find the services and support that make sense.

Best in class revenue Optimization

Demonstrated Earnings

Your investment is important. Our partners have proven they can substantially increase revenue on properties over market averages.

Accuracy with our technology

Tech-Forward Focus

The best property managers use data to make smart decisions, and technology to create seamless guest experiences.

Trusted brand reputation

Trusted Brand Reputation

We partner with property managers with Superhost status and high guest ratings, so guests always know what to expect.

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Who’s a good fit for a professional manager?

You think your short-term rental can make more money

Your property is not beating market averages, getting enough bookings, or does not have visibility across the major rental platforms.

You want a partner where you are valued

Our preferred managers build personal relationships with all of their owners and care about each property like it's their own.

You want hassle-free hosting

Whether you're down the street or a flight away, dealing with guest inquiries, cleaning, and everything in between is too time consuming and challenging.

Ready To Get Started Form

Get connected

We'd love to hear about what you're looking for, and we’ll connect you with top vacation property managers in your area!

FAQ

Answers to common questions

What is vacation rental property management?

Vacation rental property management is a service provider that maintains and improves a vacation rental on behalf of owners. They manage the ongoing operation, marketing, maintenance, and promotion of a vacation rental, short-term rental, or Airbnb property.

What services does a vacation rental manager offer?

Most managers offer partial or complete end-to-end management of vacation rental properties. Complete management includes all aspects of home maintenance, cleaning, guest and host communications, and marketing, pricing, and promotion of your property. In addition to these services, Summer connects owners and hosts with professional design and investing services for their vacation home.

Can they help me convert an existing home into a vacation rental?

Absolutely! Many property managers do onboard homes that were recently purchased or are being converted into vacation rentals. The best teams will provide advice, guidance, and services to help your home prepare for its short-term rental launch.

How long does the onboarding process take?

The onboarding process usually takes 2-4 weeks. This gives the manager and owner ample time to inspect the property, get it ready for guests, and get the listing live. In the event that owners need additional time to furnish or otherwise improve the property, the onboarding process can be extended.

Will I get a smart lock?

Yes, most managers provide a smart lock. This helps them operate the home and seamlessly let guests in. While there is some upfront expense associated with the lock and some additional time to set it up, there’s nothing worse than a guest not being able to access the property when they arrive.

Will they take updated photos of the property?

In most cases, your manager will hire a professional photographer to do a shoot at the home. This happens after the home is both cleaned and staged for photography. This helps the home stand out on vacation rental booking sites and results in better bookings overall. If you have really high-quality photos already, you can skip this step in the onboarding process.

How do I know my property will be safe with guests?

Professional managers put a number of security measures in place at the home to monitor noise and avoid unwanted guests in the property. Most also have built-in procedures for resolving any immediate guest issues involving parties, extra guests, and anything else in violation of the booking and local laws and requirements.