Bennington, Vermont, nestled in the picturesque Green Mountains, offers charming short-term rental opportunities in a quintessential New England setting that attracts visitors year-round with its combination of natural beauty, rich history, and cultural attractions. The town's location in southwestern Vermont makes it an ideal base for exploring the region's famous fall foliage, winter skiing, and summer outdoor activities, while its historic downtown and proximity to Bennington College create steady demand from cultural tourists, outdoor enthusiasts, and academic visitors. Bennington's Revolutionary War heritage, celebrated at the Bennington Battle Monument, combined with its vibrant arts scene and traditional Vermont character, appeals to travelers seeking authentic New England experiences. The town's strategic position near the New York and Massachusetts borders expands its market reach, while Vermont's growing reputation as a destination for agritourism, craft beverages, and outdoor recreation continues to drive visitor growth and rental demand.
Bennington shows strong seasonal patterns with peak demand during fall foliage season (late September-October) when visitors flock to see autumn colors in the Green Mountains. Summer months (June-August) maintain solid demand from families and outdoor enthusiasts exploring Vermont's natural beauty and historic sites. Winter experiences variable demand, with strong weekends during ski season but weaker weekday occupancy. Spring offers moderate demand as weather improves and visitors return for hiking and sightseeing. The market benefits from its proximity to Massachusetts and New York, drawing weekend visitors year-round, plus special events like Bennington Battle Day celebrations creating demand spikes.
STR hosting requires compliance with VT Rental Housing Codes via inspection; recent local rules include registration fees ($150 hosted, $300 unhosted), occupancy limits, paperwork, and safety inspections (benningtonvt.org, The Offer Sheet).
Managing an Airbnb in Bennington can be challenging due to the seasonal nature of tourism and the competition from other listings. Hosts must also ensure their property is well-maintained and adequately stocked for guests. A professional Airbnb management company can assist with these tasks, ensuring that the property is always in top condition and that guests have a seamless experience.
The most sought-after amenities in Bennington include properties with historic charm, outdoor spaces like porches or gardens, and proximity to local attractions like the Bennington Monument and the Covered Bridges of Bennington County. Guests also appreciate amenities like WiFi, air conditioning, and fully-equipped kitchens. Locations close to downtown Bennington or Bennington College are also popular.
Bennington, Vermont, nestled in the picturesque Green Mountains, offers charming short-term rental opportunities in a quintessential New England setting that attracts visitors year-round with its combination of natural beauty, rich history, and cultural attractions. The town's location in southwestern Vermont makes it an ideal base for exploring the region's famous fall foliage, winter skiing, and summer outdoor activities, while its historic downtown and proximity to Bennington College create steady demand from cultural tourists, outdoor enthusiasts, and academic visitors. Bennington's Revolutionary War heritage, celebrated at the Bennington Battle Monument, combined with its vibrant arts scene and traditional Vermont character, appeals to travelers seeking authentic New England experiences. The town's strategic position near the New York and Massachusetts borders expands its market reach, while Vermont's growing reputation as a destination for agritourism, craft beverages, and outdoor recreation continues to drive visitor growth and rental demand.
Bennington shows strong seasonal patterns with peak demand during fall foliage season (late September-October) when visitors flock to see autumn colors in the Green Mountains. Summer months (June-August) maintain solid demand from families and outdoor enthusiasts exploring Vermont's natural beauty and historic sites. Winter experiences variable demand, with strong weekends during ski season but weaker weekday occupancy. Spring offers moderate demand as weather improves and visitors return for hiking and sightseeing. The market benefits from its proximity to Massachusetts and New York, drawing weekend visitors year-round, plus special events like Bennington Battle Day celebrations creating demand spikes.
Historic Old Bennington offers visitors access to the iconic Bennington Battle Monument, Old First Church, and beautifully preserved colonial architecture, making it ideal for history enthusiasts and cultural tourists. Downtown Bennington provides walkable access to local shops, restaurants, galleries, and the Bennington Museum, while serving as a convenient base for day trips throughout southern Vermont. Areas near Bennington College attract visiting academics, prospective students and families, and cultural event attendees, particularly during the academic year and special campus programs. Properties in the surrounding Green Mountain foothills offer scenic mountain views and easy access to hiking trails, ski areas, and outdoor recreation opportunities, appealing to nature lovers and seasonal visitors seeking quintessential Vermont mountain experiences.
$216
48%
15% to 30%
$36,820
STR hosting requires compliance with VT Rental Housing Codes via inspection; recent local rules include registration fees ($150 hosted, $300 unhosted), occupancy limits, paperwork, and safety inspections (benningtonvt.org, The Offer Sheet).
VT imposes a meals & rooms tax plus a 3% surcharge as of August 2024 (MSK Attorneys, Proper Insurance®).
Easy | Town says there’s no separate STR license—just comply with VT Rental Housing Code/inspections.
Bennington's rental market features primarily historic Vermont homes including colonial and Victorian properties, many converted into charming vacation rentals with period details. The market includes restored farmhouses, historic inn-style properties, modern cabins for outdoor enthusiasts, and some luxury homes with mountain views. Properties often emphasize Vermont charm with features like wood-burning fireplaces, rustic decor, and scenic settings. The inventory ranges from cozy 1-2 bedroom cottages perfect for couples to large family homes accommodating group getaways. Many properties cater to leaf-peepers in fall and skiers in winter, with hosts emphasizing seasonal amenities and local attraction proximity.
$115.67
$149.65
$189.67
$230.87
We have an experienced team and a suite of technology dedicated to providing the best service possible.
No cancellation fees
No contract lock-in
Just 90 days notice to cancel
Annual contracts with cancellation penalties
No cancellation fees
No contract lock-in
Just 90 days notice to cancel
Annual contracts with cancellation penalties
Rest well knowing your property is managed by an experienced team powered by world-class technology.
+10-30%
4.8 stars
5+ years
Awning’s team ensures your home is maintained and stocked well and always ready for its next booking.
With an always available operations and support team, we’re available to take the 2am call about the toilet to make your guest happy.
We use our data and best practices to ensure your listing performs as well as possible and makes you the most money.
Schedule a call to learn more about Awning’s Short Term Rental Property Management Service.
Get in touch about full-service vacation rental management.
Vacation rental management refers to the comprehensive management and operation of a short-term rental property, typically for vacationers or other transient guests. This includes managing bookings, coordinating cleaning and maintenance services, and ensuring the property meets all legal and safety requirements. A vacation rental manager is responsible for overseeing all aspects of the rental process, including marketing and advertising the property, communicating with guests, and collecting payments. They also ensure the property is fully furnished and equipped with essential amenities and supplies. A well-managed vacation rental can lead to positive guest experiences, increased bookings, and higher rental income.
Airbnb management involves overseeing all aspects of an Airbnb property's operations, including managing bookings, guest communications and cleaning and maintenance services. An Airbnb management service handles the day-to-day tasks associated with renting out a property, freeing up the property owner's time and resources. Airbnb managers may also provide additional services such as professional photography, pricing optimization, and guest screening. The manager typically charges a fee or commission based on a percentage of the rental income, and the property owner retains ownership and control of the property. Effective communication between the Airbnb manager and property owner is crucial to ensure the property is managed in line with the owner's goals and preferences.
Hiring a professional Airbnb manager can offer several benefits for property owners, including increased efficiency, improved guest satisfaction, and higher rental income. A professional manager can handle all aspects of the rental process, including marketing, booking management, guest communication, and property maintenance. This frees up the owner's time and resources, allowing them to focus on other priorities. An experienced manager can also optimize pricing and occupancy rates, leading to increased rental income. Additionally, a professional manager can ensure the property is well-maintained, clean, and fully equipped with essential amenities, leading to positive guest experiences, positive reviews, and ultimately, higher bookings.
Full-service vacation rental management refers to a comprehensive property management service that handles all aspects of renting out a short-term rental property for vacationers or other transient guests. A full-service vacation rental manager provides a turnkey solution for property owners, including marketing and advertising the property, managing bookings and coordinating cleaning and maintenance services. This type of management service typically includes professional photography, pricing optimization, and guest screening to ensure the property is marketed effectively and generates maximum rental income. A full-service vacation rental manager provides a hassle-free approach to managing a short-term rental investment, enabling owners to maximize their rental income without the time and effort required to manage the property themselves.
Full-service vacation rental management offers several additional benefits compared to half-service management, including:
Overall, full-service vacation rental management provides a turnkey solution for property owners, providing a hassle-free approach to maximizing rental income and guest satisfaction.
Personal use of the property is based on the annual revenue and other considerations, book a call with an advisor to learn more. As an Airbnb management company, Awning typically provides flexibility for property owners to use their properties for personal use as desired, provided that it does not conflict with existing bookings or maintenance schedules. It's important for property owners to review the management agreement and communicate any personal use plans with the management company to ensure that there are no issues or conflicts. If the property owner has any questions or concerns about personal use policies, they should discuss these with the management company to clarify any questions or concerns.
Awning property management fees typically start at 15% of revenue and vary based on several factors such as property size, type, location, and annual estimated or realized revenue. The specific management fees may vary based on the unique characteristics of the property and the level of service required. Awning provides a comprehensive range of management services, including marketing, booking management, guest communication, cleaning, and maintenance, among others. The management fees charged are a percentage of the revenue generated by the property, with a percentage ranging from 15% and higher based on the factors mentioned above.
Awning Vacation Rental Management is available in all 50 states. As a national vacation rental management company, Awning provides services to property owners across the United States, offering a comprehensive range of management services that include marketing, booking management, guest communication, cleaning, and maintenance. Awning has a team ofAwning Vacation Rental Management is available in all 50 states. As a national vacation rental management company, Awning provides services to property owners across the United States, offering a comprehensive range of management services that include marketing, booking management, guest communication, cleaning, and maintenance. Awning has a team of experienced vacation rental professionals who have extensive experience in managing short-term rental properties, ensuring that the properties are marketed effectively, guest satisfaction is high, and rental income is maximized.
Awning Vacation Rental Management offers a wide range of services to property owners, including:
Additionally, Awning offers guests additional services that they can purchase, including design, furnishing, and installation services, as well as insurance options. The company aims to provide comprehensive, full-service vacation rental management that takes care of all aspects of property management, allowing property owners to maximize their rental income without the hassle of managing the property themselves.
Yes, Awning Vacation Rental Management can help property owners convert a rental property or home into an Airbnb rental. Awning provides a comprehensive range of services that include finding, analyzing, and purchasing a vacation rental property, as well as furnishing it and managing it as an Airbnb rental. The company can help property owners through every step of the process, from identifying the ideal property to purchase and preparing it for rental, to managing bookings, guest communications, and property maintenance. Awning's team of experienced vacation rental professionals can provide personalized recommendations and guidance throughout the conversion process, ensuring that the property is optimized for maximum rental income and guest satisfaction.
Yes, Awning Vacation Rental Management manages condos on Airbnb. As a full-service vacation rental management company, Awning has extensive experience managing all types of vacation rental properties, including condos, apartments, single-family homes, and more. The company's team of experienced professionals can handle all aspects of managing a vacation rental property, from marketing and advertising to managing bookings and coordinating cleaning and maintenance services. Awning has experience managing properties in various locations and can customize its services to meet the unique needs of each property and owner. Whether you own a single condo or multiple units, Awning can help you maximize rental income and guest satisfaction.
Awning offers as many services as Vacasa at a lower price point and with more transparency. Rates for Awning property management start at 15% of revenue and all of the expenses incurred in managing the property are billed directly to the owner for full transparency.
Evolve is a half-service property manager. While it charges a lower rate starting at 10% it leaves the vast majority of the work for the owner of the property, like cleaning, guest communication, and property maintenance.
Awning Vacation Rental Management handles emergencies at the property promptly and effectively. The company has a network of local professionals who can respond quickly in case of an emergency, typically within one hour or less. This ensures that any issues or emergencies are handled promptly, minimizing the impact on the guest experience and the property owner's reputation. Additionally, Awning's team is available 24 hours per day to assist guests with any issues that may arise during their stay, from maintenance issues to guest complaints. This ensures that guests are well taken care of, which can lead to positive reviews and increased rental income. Awning's commitment to providing high-quality emergency management services is one of the key reasons why property owners choose the company to manage their vacation rental properties.
Yes, Awning Vacation Rental Management offers insurance for hosts and their properties. The company provides insurance options that cover both the property and the vacation rental income, protecting the host from the financial risk of any activities on the property conducted in connection with running the Airbnb rental. The specific insurance rate may vary depending on the unique characteristics of the property and the level of coverage required. Awning can provide customized insurance solutions that meet the specific needs of each property and owner, providing peace of mind and protecting the property and the host from any unforeseen issues or liabilities. Property owners interested in learning more about Awning's insurance options can contact the company for more information.
company provides professional design and furnishing services that are specifically tailored to meet the needs of vacation rental properties. Awning's team of experienced professionals can work with property owners to select and install furnishings and decor that are functional, durable, and aesthetically pleasing, ensuring that the property stands out in the competitive vacation rental market. By providing professional design and furnishing services, Awning enables property owners to create a unique and attractive space that is optimized for maximum guest satisfaction and rental income. The company's furnishing services are designed to save property owners time and effort, allowing them to focus on other aspects of managing their vacation rental properties.
Yes, Awning Vacation Rental Management will maintain amenities like pools and hot tubs for hosts. The company provides a comprehensive range of maintenance services, including pool and hot tub maintenance, lawn maintenance, cleaning services, and more. Awning's team of experienced professionals can ensure that all amenities are well-maintained and guest-ready, minimizing the risk of issues or problems that could impact the guest experience. By providing maintenance services, Awning enables property owners to focus on other aspects of managing their vacation rental properties, such as marketing, guest communication, and booking management, while ensuring that the property is well-maintained and optimized for maximum rental income.
The timeline for Awning Vacation Rental Management to take over management of a property can vary depending on the property's current state and the services required. If the property is already operating as an Airbnb, Awning can take over management within a few days, assuming that all necessary information and access is provided. For new properties that need to be set up for vacation rental management, the process can take between 1-4 weeks, depending on the specific needs of the property, such as the installation of smart locks or other amenities. For properties that require design and furnishing services, the setup process can take longer, typically 6-8 weeks to get them live. During the setup process, Awning's team works closely with property owners to ensure a smooth transition and minimize any disruption to existing bookings or rental income.
Yes, Awning Vacation Rental Management uses technology to price vacation rental properties. As a technology-driven company, Awning has access to the best Airbnb data, which it uses to build tools for its hosts, investors, and internal use. Pricing is handled by Awning's team of experienced professionals, who use data-driven insights to ensure that the property's revenue is maximized while minimizing risks such as property damage, canceled bookings, and wear and tear. Awning's pricing strategies are designed to be dynamic, taking into account factors such as demand, seasonality, and local events to ensure that the property is priced competitively and generates maximum rental income. By leveraging technology and data, Awning can provide personalized pricing strategies that are tailored to the specific needs and characteristics of each vacation rental property.
The pet policy for homes under Awning Vacation Rental Management is determined by the property owner. Awning follows the desired pet policy of the property owner, which can vary depending on the owner's preferences and the specific characteristics of the property. Some property owners may choose to allow pets, while others may prefer to restrict pets or prohibit them entirely. Awning can work with property owners to establish a pet policy that meets their specific needs and goals, while also ensuring the comfort and safety of guests and the property itself. If pets are allowed, Awning can provide guidance on best practices for pet management, such as additional cleaning and maintenance services, to minimize any potential issues that may arise from having pets in the rental property.
