Holiday houses in Greensboro

Romantic NEK Log Cabin w/ Hot Tub & Fireplace

“It felt like staying at a dear friend’s cabin — one with wonderful taste who thinks of everything.” A quiet, romantic cabin for unplugging and resetting. Tucked on a wooded hillside, this romantic log cabin blends rustic soul with refined comfort. Blankets beckon, textures are rich, and every detail is intentional. Real art, fine furnishings, and luxury bedding create a feeling of quiet ease. Not just a place to stay, but a thoughtfully curated retreat you’ll want to return to year after year.

Family · Value · Pets

Vintage, Off-Grid Airstream in the Woods by Stream

Surrounded by forest and the sound of a flowing brook, Fallingwater Airstream is a place to slow down and reconnect. Sip coffee on the deck, sway in the hammock overlooking the water, and gather by the fire beneath a sky full of stars. Perfect for couples seeking a quiet escape, this lovingly restored 1965 Airstream offers vintage charm and simple comforts—an introvert’s paradise for rest, solitude, and rejuvenation, with just enough warmth to make this woodland glamping stay feel truly special.

Location · Value · Decor

Bunkhouse on Caspian Lake

Take a break and unwind at our rural cottage on the lake. Equipped with full kitchen and bath, main bedroom with a king bed and 2 additional bedrooms with full beds. The house is situated on a hill with kayaks available for use. Enjoy miles of hiking trails at the Nature Conservancy's 256-acre Barr Hill Preserve, or biking on the extensive Lamoille Valley Rail Trail. Greensboro has an historic general store (Willey's) and the award-winning brewery, Hill Farmstead, is nearby in Greensboro Bend.

Location · Family · Comfort

Farmhouse in VT’s idyllic NEK

Our renovated farmhouse in Greensboro is a comfortable, restorative place for groups of family, friends, and guests. The oldest part of the house dates from 1830, and the whole structure has been extensively restored without losing its simple charm. Use it for easy access to the many attractions—e.g., hiking, skiing, biking, lakes, world-class beer and cheese, and farm-fresh produce and meat—that Greensboro and the rest of the NEK have to offer, and/or just to relax in a quiet rural setting.

Family · Location · Hiking

Cozy retreat in Northeast kingdom Greensboro VT

Relax in this calm, stylish space. The guest unit (1 queen bed+a pull out couch) was built in 2023. Located on an extremely quiet rise well back from the road and overlooking Caspian Lake. Cross-country skiing right out the door. Less than 1 hour away from Stowe and Burke Mt, 10 minutes to Hill Farmstead Brewery or Barr Hill, minutes away to library, tennis, golf, art center, public beach, stores. Easy access to the trail network of Highland Lodge and Craftsbury Outdoor Center.

Family · Location · Sleep quality

Vermont Log Home with Panoramic Mountain Views

A spacious light-filled log home in the heart of the Northeast Kingdom, with open kitchen, living room, sun room, wraparound deck, & basement ping-pong. Dazzling views of the Green Mountains and huge lawn for relaxation & play. Minutes from the 4-season Craftsbury Outdoor Center, Craftsbury General Store, Caspian Lake swimming, & the Hill Farmstead & Brewery. 50-minute drive to skiing & water park at Jay Peak, an hour to Stowe Mountain. Wood stove in the living room and free wifi.

Family · Value · Amenities

Ann’s Schoolhouse

Ann’s Schoolhouse is a beautiful Historic Schoolhouse built in 1901 and nestled in the green mountains of Vermont. Complete with the original school bell, chalk board and desks from 1901 you'll take a trip back in time when you visit! You and your family will love the quiet serenity as you sit by the fire pit and take in the views. This cozy home is perfect for your family vacation or event, couples weekend away or a friends trip. You'll love calling Ann's Schoolhouse home!

Location · Family · Checkout

Family Retreat | 50 Private Acres | Mountain Views

Nestled on 50 private acres in Vermont's beautiful Northeast Kingdom, Vermont Escape has been part of our family for three generations. Cared for since 2001 as a peaceful retreat from busy lives, the home offers sweeping mountain views, spectacular sunsets, and the privacy that makes this corner of Vermont so special. Relax on the wraparound deck while grilling dinner, enjoy a morning coffee as the valleys come alive, or simply unwind and reconnect with family and friends.

Family · Location · Indoor spaces

Relaxing Craftsbury Retreat

One bedroom house in pastoral setting with deck, small pond and screened in sitting area. Newly renovated kitchen and full bath. Kick back with a book in front of the stove after a day on the trails or out on the amazing NE kingdom gravel roads at the Craftsbury Outdoor Center (4 mi). Short stroll to maple buns at the Genny or Creemees at Village Store (1/2 mi). Spend the day on the lake at Caspian (8 mi). Stock up at Hill Farmstead Brewery (10 mi).

Value · Location · Access

Secluded Paradise in Greensboro on Barr Hill

Cozy, private, one-of-a-kind property tucked in the folds of Barr Hill, a half a mile from nordic trail access, a few miles from Hill Farmstead Brewery. Perched on fifteen acres of private land surrounded by grass, fruit trees, wildlife, and miles of forest, "Sherry's Place" is an experience of pure bliss and seclusion in nature. (The large screen porch is accessible but too cold for most uses in winter.) Modern, brand-new appliances.

Location · Family · Comfort

Bright, Spacious Family Getaway with Private Beach

Relax with the whole family at this private but conveniently-located home. Walk down a dirt lane to your own 50' private beach on the north shore of Caspian Lake. Eat veggies from the garden and apples from the trees. Enjoy the flowerbeds, and take a walk through the woods on marked trails. In summer, hear beautiful hermit thrush song all day. The house is well-equipped and comfortable, with fast Starlink internet and a nice TV.

Family · Location · Walkability

Rustic Retreat on COC Trails/Near Hill Farmstead

This simple home is the place to go to turn off your phone, breathe, and unwind. Located down a dirt road and on our town's world class cross country ski trail system, it's a 5 min drive to the Craftsbury Outdoor Center and 15 m to Hill Farmstead/Jasper Hill Farm. Close to many places to hike, kayak, downhill ski, and more, the Airbnb is also near many local artists, breweries, and restaurants (Blackbird! Hill Farmstead!).

Value · Family · Cleanliness