Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Montgomery, Vermont
In Montgomery, Vermont, guests can find a variety of Airbnb accommodations that cater to different preferences and group sizes. The area offers charming rustic cabins and cozy cottages, perfect for those looking to enjoy the serene natural surroundings and the quintessential Vermont experience. Many of these properties feature amenities such as fireplaces, hot tubs, and scenic mountain views, ideal for a relaxing getaway. Additionally, there are spacious farmhouses and modern homes available, which are well-suited for families or larger groups seeking more space and comfort. Some Airbnbs in Montgomery also provide easy access to outdoor activities like skiing, hiking, and exploring the nearby Jay Peak Resort, making them an excellent choice for adventure enthusiasts.
As of the latest information, Montgomery, Vermont does not have specific local laws governing Airbnb or short-term rentals. However, hosts in Montgomery must comply with Vermont state regulations, which require short-term rental operators to register with the Vermont Department of Taxes and collect the state's 9% Rooms and Meals Tax from guests. Additionally, hosts should ensure their properties meet health and safety standards as outlined by the state. While Montgomery itself may not have distinct ordinances for short-term rentals, property owners should stay informed about any potential changes in local regulations and ensure compliance with broader state requirements.
Managing an Airbnb in Montgomery, Vermont, 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, especially given the area's appeal for outdoor activities like skiing and hiking. Effective communication with guests is crucial, from promptly responding to inquiries and booking requests to providing detailed check-in instructions and local recommendations. Additionally, managing bookings to optimize occupancy rates, setting competitive pricing based on seasonal demand, and handling any guest issues or emergencies are essential. Given Montgomery's rural setting, hosts should also consider partnerships with local businesses to enhance guest experiences and potentially offer unique packages or discounts.
Montgomery, Vermont, is a charming town known for its picturesque landscapes and proximity to outdoor activities, making it an ideal destination for an Airbnb stay. The best areas to consider are near the Jay Peak Resort, which offers year-round activities including skiing, hiking, and golfing. Staying close to the resort provides easy access to these amenities while also offering stunning mountain views. Another great area is the village center of Montgomery, where you can enjoy the quaint, small-town atmosphere with local shops, cafes, and historic sites. This location provides a more relaxed setting while still being a short drive from outdoor adventures. Both areas offer a blend of natural beauty and convenience, making them perfect for a memorable stay.
Montgomery, Vermont, is an appealing market for Airbnb investment due to its picturesque setting and proximity to popular outdoor attractions. Nestled near the Jay Peak Resort, the area attracts visitors year-round for skiing, snowboarding, and hiking, making it a desirable location for short-term rentals. The town's charming rural atmosphere, combined with its vibrant local community and events, enhances its appeal to tourists seeking a peaceful retreat. Additionally, the relatively low property prices compared to other vacation hotspots in Vermont offer a potentially lucrative opportunity for investors looking to capitalize on the growing demand for unique and cozy accommodations in a serene environment.
As of the latest data, the average Airbnb revenue in Montgomery, Vermont, reflects a modest yet steady income for hosts, driven by the town's appeal as a serene getaway destination. Nestled near the picturesque Green Mountains and close to popular attractions like Jay Peak Resort, Montgomery attracts visitors year-round, particularly during the ski season and fall foliage period. The average revenue is influenced by factors such as property type, location, amenities offered, and seasonal demand. Hosts in Montgomery typically see higher occupancy rates and revenue during peak tourist seasons, while off-peak times may require strategic pricing and marketing to maintain bookings. Overall, Montgomery's Airbnb market offers a promising opportunity for hosts who can capitalize on the area's natural beauty and recreational offerings.
Montgomery, Vermont, experiences a fluctuating occupancy rate for Airbnbs, largely influenced by its seasonal attractions. The town is a popular destination for outdoor enthusiasts, particularly during the winter months due to its proximity to the Jay Peak Resort, which boosts occupancy rates as visitors flock for skiing and snowboarding. The summer months also see a rise in bookings, as tourists come to enjoy hiking, fishing, and the scenic beauty of the Green Mountains. However, the shoulder seasons of spring and fall typically witness a dip in occupancy, as the town transitions between its peak tourist activities. Overall, Montgomery's Airbnb market is characterized by high demand during the winter and summer, with quieter periods in the transitional seasons.
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.