Forget the crowds. These six Vermont vacation-rental homes put you along the Route 100 corridor and the Killington-Pittsfield border—prime territory for Appalachian Trail hiking, secluded pond swimming, and some of the best leaf-peeping in New England. Whether you want direct water access on Kent Pond or a quiet perch near Sherburne Pass, these three- and four-bedroom homes offer a distinctive slice of the Green Mountains.
Killington isn’t just a winter destination. Come summer, the Appalachian Trail and Long Trail converge here, offering everything from easy boardwalk strolls to 4,000-foot summit hikes. Kent Pond provides cool water for post-hike swimming, while Sherburne Pass serves as the gateway to waterfall hikes and panoramic vistas of the Coolidge Range. In autumn, Route 100 transforms into a foliage highway, winding through national forest and past classic Vermont villages.
The Resort Proximity Options
The Maple Leaf: Indoor Hot Tub & Dual Living Spaces
Located just five minutes from the Killington Resort, The Maple Leaf —a standalone 3-bedroom home on a quiet wooded lot— offers something rare: an indoor hot tub room usable year-round regardless of weather. For hikers caught in an afternoon thunderstorm or returning from a chilly autumn summit, this is a game-changer.
The layout features two full living rooms—one with a wood-burning fireplace, one with a propane stove—so night owls can socialize while early risers sleep. In fall, you’re few minutes from the Green Mountain National Golf Course, which offers 18 holes surrounded by peak foliage. The location also puts you close to the Sherburne Pass trailhead, where you can hike the Deer Leap Trail for panoramic views of the Coolidge Range without committing to a full 4,000-footer climb.
The Currier Crossing: Family & Pet Friendly
Located slightly farther from the resort—about twelve minutes—The Currier Crossing trades proximity for space and flexibility. One of our 4-bedroom Killington homes, this family-oriented property includes a travel crib, baby monitor, stair gate, and children’s books. Pets are welcome here.
The bonus living room with foosball table keeps kids entertained during rainy summer afternoons, while two furnished decks and a garden provide outdoor space. The quieter setting brings darker skies, ideal for stargazing, and you’re still within easy driving distance of the Pico Mountain hiking trails and the town of Rutland for dining.
Full Send Bend: The Social Hub
Close to Pico Mountain, 4-bedroom Full Send Bend features a detached game room above the garage—a separate social space with a pool table that prevents noise from carrying to the main house. This renovated home is ideal for groups with mixed bedtimes or teenagers who want their own space.
The massive multi-level deck with custom shade sails overlooks the surrounding forest, providing an outdoor living room for summer barbecues. In fall, you’re nearest to the Sherburne Pass area, where the Route 100 scenic drive offers some of the most photographed foliage views in the state. The Thundering Falls boardwalk—an accessible trail to a 140-foot waterfall—is just minutes away by car.
The Quiet Borderlands: Powder Run & Peak Hill Home
These two properties sit on the Killington-Pittsfield border, just off the main resort corridor. Pittsfield is the nearest neighborhood to the north—a classic Vermont town along the Route 100 corridor that offers a quieter alternative to staying in the resort village. You’re tucked into the woods here, but still within a ten-minute drive of the mountain.
Powder Run: The Modern Mountain Base
A new-build home with 2,100 square feet of space, Powder Run (3 bedrooms) offers a private patio and hot tub for recovering after long days on the trail. The location on the border means mornings where you might spot deer in the flat, wooded parking area.
Inside, the Great Room features coffered ceilings and a gas stove, while the kitchen is equipped for real cooking after a day of hiking. A whole-home generator ensures summer storms won’t interrupt your stay, and the Level 2 EV charger makes this an easy choice for electric vehicle owners exploring Vermont’s scenic byways. In fall, you’re perfectly positioned to drive Route 100 north toward Waterbury—one of the state’s signature foliage corridors—or head south to explore the Green Mountain Club’s recommended leaf-peeping trails.
Peak Hill Home: The Compact Bunkhouse
Freshly rebuilt and nestled in the same wooded border area, Peak Hill Home is another 3-bedroom property that offers an intimate setting. The vaulted living room with skylights brings the forest inside, while the large deck and fire pit provide outdoor gathering space.
This location shines in summer and fall when the hosts offer complimentary golf, mountain biking, gondola, and adventure center passes (limited availability)—perks that let you explore the mountain without the lift ticket prices. The ski storage shed doubles perfectly for bike storage, and the flat lot makes unloading kayaks or hiking gear hassle-free. From here, it’s an easy drive to Thundering Brook Falls, where a wheelchair-accessible boardwalk leads to one of Vermont’s tallest waterfalls.
The Water Access Outlier
Lakewood Lodge: Kent Pond Frontage
Lakewood Lodge (4 bedrooms) offers rare private waterfront access. A short walk down a marked path leads to Kent Pond, a 29-acre body of water nestled between the mountains. According to the Rutland County Audubon Society, this is a prime birding spot—look for common loons, osprey, bald eagles, and spotted sandpipers along the shoreline.
In summer, the pond offers swimming, kayaking, and fishing. You can paddle out for a quiet tour of the shoreline or simply relax by the water and watch the wildlife. The house itself is a classic multi-level Vermont home with a fieldstone fireplace for cool autumn evenings and a seven-person hot tub on a bluestone patio. This home sits close to Route 100, providing quick access to the Green Mountain National Golf Course just down the road.
Summer & Fall Activities by Location
Hiking: All of these Vermont properties provide access to the Green Mountain Club’s recommended trails. From Lakewood Lodge, walk the Appalachian Trail to Kent Pond. From Powder Run or Peak Hill, drive to the Sherburne Pass trailhead for Deer Leap or Pico Peak. Full Send Bend puts you closest to the Killington Peak summit trails.
Water Activities: Only Lakewood Lodge offers direct Kent Pond access for swimming and paddling. The others are within driving distance of the pond’s public access points or other local swimming holes.
Fall Foliage: The border properties (Powder Run and Peak Hill) offer the darkest skies and quietest roads for autumn drives. Route 100—the “Skier’s Highway”—transforms into a foliage corridor running past national forest. The higher elevation of the Pittsfield border area often means earlier peak color than the valley floor.
Golf: The Green Mountain National Golf Course sits near Route 100, close to the properties, especially Lakewood Lodge and The Maple Leaf. This 18-hole, par-71 championship course designed by Gene Bates plays 6,589 yards through the mountains with distinct elevation changes and bent grass fairways. The 16th tee offers panoramic views of the Coolidge Range—especially vivid during fall foliage season—and the layout features centuries-old glacial rock formations throughout. Open late spring through October.
Birding: Kent Pond is the standout here, with documented sightings of loons, osprey, and even the occasional American white pelican. Early mornings on any of the properties may yield sightings of turkey, deer, and the region’s numerous songbirds.
Horseback Riding: Several stables near the area offer guided rides along woodland trails and open meadows. Whether you are a beginner looking for a gentle walk or an experienced rider seeking terrain with elevation, local outfitters provide mounts suited to various skill levels. This is a serene way to experience the fall foliage without the effort of hiking.
Mountain Biking: When the snow melts, Killington Resort transforms into a lift-served bike park with over 45 miles of trails. Moreover, the properties near Kent Pond and Sherburne Pass provide direct access to cross-country singletrack that winds through national forest. Lakewood Lodge guests can pedal from their driveway to gravel roads around the pond, while those staying at Full Send Bend or The Currier Crossing are minutes from the Pico Mountain trails, where old logging roads offer sustained climbs and technical descents through hardwood forest. In fall, these same trails double as leaf-peeping routes, with the golden birch and red maple canopy creating a tunnel of color overhead.
Our property management at Simple Vacation Rentals, a leading Killington vacation rentals agency, features contactless check-ins, a local management team, and curated guides to spots most tourists miss. The primary renter’s minimum age is 25 across the portfolio. Book direct for best rates and exclusive perks.
