Performance indicators for the Montgomery short-term rental market based on reliable data.
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The highest-performing listings in Montgomery.
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Generally Investor friendly
STRs are allowed citywide in select districts, require conditional‑use approval and a moderate registration fee ($100–$250), and are enforced civilly. Tight zoning limits and added steps (insurance, local emergency contact, fire‑safety for >8 guests) raise cost/compliance but remain manageable.
Local STR Agent
STR specialist · Montgomery, VT
Montgomery is a small rural town in Franklin County in the far northern reaches of Vermont, set in the rolling, forested landscape of the Northeast Kingdom. With a population of roughly 1,200 residents, it has the quiet, outdoorsy character typical of the region — a place of winding country roads, working farms, and dense woodlands that turn brilliant with color each fall. Montgomery is best known as one of the gateway communities to Jay Peak, and it draws a steady stream of visitors year-round for outdoor recreation. The nearest major city is Burlington, Vermont, which sits approximately 70 miles to the southwest and is reached in about an hour and a half by car. Montreal, Canada, lies roughly 90 miles to the northwest.
The standout attraction in the area is Jay Peak Resort, one of the northernmost ski mountains in New England and the dominant reason most visitors find their way to Montgomery. The resort offers alpine skiing and snowboarding in the winter months, an acclaimed Nordic and cross-country trail network, and the Pump House Indoor Waterpark, which operates year-round. Jay Peak is only about a ten-minute drive from Montgomery Center, making the town a natural home base for guests who want ski-in proximity without paying ski-side prices.
A quieter but rewarding draw is the Hazen's Notch Association, a nonprofit conservation organization that maintains an extensive network of hiking, cross-country skiing, and backcountry trails on conserved land straddling the Montgomery–Westfield border. The notch itself, known as Hazen's Notch, is a scenic mountain pass that has been a travel route since early settlement days, and several trailheads are accessible within a short drive of the village. The association's properties are popular with visitors looking for a more low-key, self-guided outdoor experience than the resort provides.
For travelers interested in the broader region, Montgomery sits within easy reach of Lake Memphremagog, a long, glacier-carved lake that straddles the Vermont–Quebec border and is famous for its summer sailing, its resident lake monster legend "Memphré," and the lakeside town of Newport, Vermont, which is roughly forty minutes to the east. The Canadian border crossings at East Richford and at the hamlet of West Berkshire are also nearby, offering easy day-trip options into Quebec for travelers who want to explore the Eastern Townships.
Montgomery's appeal as a short-term rental market comes from the contrast it offers: a genuine, low-key Vermont village atmosphere paired with immediate access to Jay Peak's year-round amenities. Guests get the calm of a small country town, scenic drives through the Northeast Kingdom, and abundant outdoor adventure within a short window of their front door — a combination that makes the area attractive in every season.