Vermont’s Most Unique Airbnbs & Vacation Rentals

by Mac Misseldine

Off-the-grid cabin in Vermont

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Ready to spice up your weekend getaway to the Green Mountain State?  

When Airbnb first started, the Silicon Valley unicorn was all about connecting travelers with local homeowners who had a spare room to rent out. You can still see those roots in the company’s name, as Airbnb is short for “airbed and breakfast.”

You’ll still find plenty of spare rooms and airbeds for rent on the cheap at Airbnb, but the lodging company has definitely evolved over the years.

Today, in addition to offering a wide collection of whole-property vacation rentals, Airbnb hosts a surprisingly large connection of unique vacation rentals. Think tipis, treehouses, barns, rustic off-the-grid cabins — and that’s just the tip of the iceberg.

You’ll also find a handful of unique vacation rentals on rival sites like Vrbo and Glamping Hub, but it’s safe to say that Airbnb offers the most — and arguably the best — one-of-a-kind rental properties. 

Unique Vacation Rentals In Vermont

Whether you’re heading to Vermont for business, pleasure, or a little bit of both, we’ve got you covered.

Here’s a list of the most unique Airbnbs and vacation rentals in the Green Mountain State, starting with a property that’s straight from the pages of The Hobbit.

The Hill Hobbit House

The Hill Hobbit House Airbnb in Vermont

Why you should go: Plucked from the pages of the beloved Tolkien series, The Hill transports guests from Vermont to the rolling countryside of the Shire. 

  • Sleeps: 3
  • Minimum stay: 2 nights
  • Pets allowed: Yes

The Hill is arguably the most enviable vacation rental in the country for fans of The Hobbit and The Lord of the Rings. Where else can you spend the night in an authentic hobbit house carved into the hill? 

As utterly delightful as The Hill is on the outside, you’ll be even more impressed when you step inside. The 1,100 square foot interior features fantastical flourishes, antique furniture, and an abundance of Tolkien references that’ll make you feel like you’re actually in the Shire. 

The interior is split into two uniquely-themed sections — Baggs Inn houses the living quarters, while the Double Dragon Inn offers a pub-style dining and entertaining area that’ll have you craving a pint.  

Check Availability — Airbnb

Kingsley Barn

Kingsley Barn vacation rental in Vermont

Why you should stay here: A beautifully renovated barn in the heart of the historic village of South Woodstock.

  • Sleeps: 6
  • Minimum stay: 2-6 nights
  • Pets allowed: With permission

Overlooking the Kedron Brook and photogenic fields, the historic Kingsley Barn is conveniently situated in the heart of South Woodstock. Walk to breakfast at the South Woodstock Country Store, swim at the nearby Kedron Valley Inn, or take a quick jaunt over to the Green Mountain Horse Association for horseback riding. 

Visiting in the winter? Be sure to bring your snowmobiles, because the Kingsley Barn is right on the vaunted VAST trail network. If you’re in the mood for skiing and snowboarding, grab your gear and head to the nearby Okemo, Killington, or Suicide Six ski areas.

Check Availability — Vrbo Check Availability — Airbnb

The Hermit Thrush Treehouse

The Hermit Thrush Treehouse in Vermont

Why you should stay here: A magical treehouse that’s organically intermingled with the trees. 

  • Sleeps: 5
  • Minimum stay: 2 nights
  • Pets allowed: Yes

Treehouses are getting popular on vacation rental sites, but you won’t find anything like the Hermit Thrush Treehouse. Browse through the photos and you’ll quickly see that this is one of those rare vacation rentals that the kids will be talking about for years to come.

The Hermit Thrush Treehouse is designed to complement the surrounding forest, providing an enchanting experience that feels like you’re living inside a hollowed-out tree. The quirky architecture is memorable, the hand-carved furniture marvelous, and the open-air pavilion is sure to create family memories as you cook up backcountry cuisine and play games at the wood-carved picnic table.

Check Availability — Vrbo Check Availability — Airbnb

The Stowe Glass House

The Stowe Glass House in Vermont

Why you should stay here: An extraordinary property with stunning architectural design, where the panoramic views take center stage.

  • Sleeps: 12
  • Minimum stay: 3-7 nights
  • Pets allowed: No

The Stowe Glass House carries a premium price tag, but it’s guaranteed to deliver a retreat unlike any other. Floor-to-ceiling windows deliver stunning views of the mountains and foliage from every room in the house, and there’s a wraparound deck where you can soak up the sun and fresh air with a cup of coffee. 

Fall and winter are simply spectacular here, but you’ll want to visit during the warmer months if you want to take advantage of the pool and outdoor BBQ area.

Follow ’em: Instagram

Check Availability — Vrbo

Upper Pines Lodge

Upper Pines Lodge in Vermont

Why you should stay here: A magnificent, custom-designed lodge offering 10 acres of peaceful seclusion and scenic mountain vistas.

  • Sleeps: 10
  • Minimum stay: 2-4 nights
  • Pets allowed: No

Located in Warren, Vermont, the Upper Pines Lodge is a unique A-frame lodge sitting on 10 acres of lush landscape. The architect and interior designer both deserve heaps of praise, as this mountain retreat is positively magnificent inside and out.

This vacation rental is particularly popular over the winter, when guests can enjoy Nordic skiing at the Blueberry Lake Cross Country Center or carve powder at the Sugarbush ski resort. Over the summer, the local area offers swimming holes, fishing, waterfalls, and an abundance of hiking trails.

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Mount Snow/Stratton Estate

Mount Snow-Stratton Estate in Vermont

Why you should stay here: A sprawling 100-acre estate with enough indoor and outdoor activities to entertain a group of 20 for weeks.

  • Sleeps: 21
  • Minimum stay: 2-7 nights
  • Pets allowed: Yes

Boasting 6,000 square feet of living space, beds for up to 21 guests, and a whopping 100 acres of privacy, this gargantuan estate in Newfane is a prime vacation rental for large groups and retreats.

The main house features six bedrooms, a cavernous family room with a fireplace and wood burning stove, and ample space to entertain. Head to the guest house and you’ll find one more bedroom and a game room with a wet bar, pool table, ping pong table, foosball table, cards table, and sauna.

When you’re ready to venture outside for fresh air and sunshine, the property offers a swimming pool, jacuzzi, tennis court, and outdoor fire pit. The property features miles of hiking trails, with Mount Snow and Stratton Mountain nearby for further exploration.

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Solar Geodesic Dome

Solar Geodesic Dome in Vermont

Why you should stay here: Explore the “green” side of the Green Mountain State in this solar-powered, geodesic dome.

  • Sleeps: 6
  • Minimum stay: 2-4 nights
  • Pets allowed: Yes

Go completely off the grid with this geodesic dome in Albany, Vermont. The solar-powered home is quirky inside and out, perfect for travelers in search of a particularly unique vacation rental.

In addition to being remarkably peculiar, it’s conveniently located near a number of rivers, lakes, golf courses, and trails, making it an excellent destination for hiking, mountain biking, fishing, boating, and golfing. When winter brings fresh powder, guests will be a quick 10-minute drive from the Craftsbury Nordic Center, and there are four ski areas within a 40-minute drive of the property.

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Hickory Ridge Log Cabin

Hickory Ridge Lodge Cabin in Vermont

Why you should stay here: An artistic cabin set on a homestead property surrounded by fruit trees, berries, gardens, and naturally terraced terrain.

  • Sleeps: 10
  • Minimum stay: 2-4 nights
  • Pets allowed: Yes

There are a number of log cabin rentals available across Vermont, but you won’t find any like the Hickory Ridge Log Cabin. From the naturally warped wood accents outside to the cave-like fireplace and rustic timbers throughout the house, it’s a truly unique cabin with marvelous architectural flourishes.

The Hickory Ridge Log Cabin can accommodate up to 10 guests, but if you need more beds and living space be sure to book the other unique vacation rental on the property — the Hermit Thrush Treehouse

Check Availability — Vrbo Check Availability — Airbnb

The Trailside Inn

Trailside Inn vacation rental in Vermont

Why you should stay here: A rustic 37-room inn overlooking the best golf course in Vermont, with room for you and 99 of your closest friends.

  • Sleeps: 100
  • Minimum stay: 2 nights
  • Pets allowed: No

Boasting sleeping accommodations for 100 (that’s right, triple digit capacity) and entertaining space for even more, the Trailside Inn is a superb choice for large wedding parties, family reunions, and corporate retreats. The hosts are happy to assist with on-site activities, catering, rentals, and discounted lift passes Killington Ski Resort, making your big gathering even easier to plan. 

Note that the nightly rate fluctuates based on the number of rooms used, season, and event type, and you’ll generally find more attractive rates on weekdays than weekends.

Follow ’em: Instagram

Check Availability — Vrbo

The Log Estate

Stratton Okemo Bromley in Vermont

Why you should stay here: It’s not a log cabin — it’s a log estate.

  • Sleeps: 30
  • Minimum stay: 2-7 nights
  • Pets allowed: Yes

The Log Estate is situated on 20 acres of land in the picturesque village of Peru, Vermont, right in the middle of Green Mountain National Forest. This enviable retreat is like a Russian nesting doll — an opulent estate nestled on a majestic tract of land encompassed by a scenic National Forest. It just gets better and better with each layer.

The Log Estate features two log cabins connected by a sprawling 4,000 square foot deck. Enjoy al fresco meals in the fresh mountain air, take a dip in the swimming pool, soak in the warmth and views from the jacuzzi, or roast some marshmallows at the fire pit.

There’s also a brand new sauna where you can relax and rejuvenate after a long day of skiing at Bromley, Magic Mountain, Stratton, or Okemo. 

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The Matterhorn House

The Matterhorn House in Vermont

Why you should stay here: A ski-in/ski-out chalet boasting unbelievable mountain views. 

  • Sleeps: 16
  • Minimum stay: 2-5 nights
  • Pets allowed: Yes

The exterior of the Matterhorn House is kinda funky, but step inside and you’ll discover an epic vacation rental for large families and groups. Thanks to extensive renovations, the well-designed interior sports beautiful wood floors, a modern kitchen, upgraded bathrooms, a sauna, and a collection of hand-carved furniture throughout the house.

That said, you’ll find the true beauty of this property from the porch. The treetop vistas from the deck are simply phenomenal, especially when fall colors are on full display. Bring your swimsuit and you can enjoy the incredible view from the comfort of the jacuzzi.

Oh yeah — it’s also a ski-in/ski-out property, conveniently situated near the Great Eastern Ski Trail at Killington Ski Resort. Ride the Killington Skyeship Gondola up the mountain and you can ski right up to your door.

Check Availability — Vrbo Check Availability — Airbnb

1961 Airstream Tradewind Land Yacht

1961 Airstream Tradewind Land Yacht Airbnb in Vermont

Why you should go: Enjoy a glamping retreat for two in a vintage Airstream trailer.

  • Sleeps: 2
  • Minimum stay: 2 nights
  • Pets allowed: No

There’s something especially nostalgic about glamping in an old-school Airstream. It ain’t the Four Seasons, but it’s one of the best ways to experience mother nature’s four seasons in the great outdoors.   

You’ll find this classic ’61 Tradewind Land Yacht in a small community 11 miles outside of Burlington. The 24-foot Airstream features cozy memory foam mattresses with heating and air conditioning, so you’ll be comfortable here year-round.

The hosts provide coffee, tea, breakfast cereal, and locally-made energy bars, and you’ll receive a gift jar of maple syrup to take home with you. 

Check Availability — Airbnb

The Yurt At La Lu Farm

La Lu Farm Yurt Airbnb in Vermont

Why you should go: It doesn’t get much more unique than a yurt on a goat farm in rural Vermont.

  • Sleeps: 2
  • Minimum stay: 1
  • Pets allowed: No

Staying in a yurt is always a unique experience, but stick that yurt on a goat farm with 70 giddy goats and you’ve got a singular glamping trip that you won’t find anywhere else.

Situated on the lower part of La Lu Farm with beautiful views of the rolling hills, the yurt affords quiet seclusion with the soothing sounds of the nearby river in the background.

Guests can rent kayaks and paddle boards from the hosts, or book an aromatherapy session for ultimate relaxation. Foodies can book a farm-to-table breakfast in the morning, attend a cooking class in the afternoon, and schedule a pizza night in the evening for delicious wood-fired pizza.        

Check Availability — Airbnb

The Tipi Retreat At Nwyfe’ Farm

Tipi Retreat at Nwyfe Farm Airbnb in Vermont

Why you should go: Camp in an authentic Native American tipi on 13 acres of forested land in Central Vermont.

  • Sleeps: 2
  • Minimum stay: 1 night
  • Pets allowed: Yes

An ideal nature retreat for couples and solo travelers, the Tipi Retreat at Nwyfe’ Farm helps guests reconnect with nature in comfort. The full-size bed ensures you’ll enjoy the best night’s sleep you’ve ever had in the woods, while the wood-burning stove will keep you warm and toasty when cold weather strikes.

Campsite amenities include a campfire pit with Adirondack chairs, a camping stove/oven combo for cooking meals, a picnic table, camping chairs, and cozy bedding. There’s a private bathhouse with a toilet, and a propane-heated shower that’s available from May to October.

Check Availability — Airbnb

Off-The-Grid Cabin In The Green Mountains

Green Mountain Cabin Airbnb in Vermont

Why you should stay here: A secluded, off-the-grid cabin where you can reconnect with nature in the Green Mountains.

  • Sleeps: 2
  • Minimum stay: 1 night
  • Pets allowed: Yes

Planning a primitive nature retreat to the Green Mountains in Vermont? Ditch your tent for this off-the-grid cabin and you’ll have a weekend getaway that you and your plus-one will be talking about for years.

For the record, pets are allowed so your plus-one can absolutely be a four-legged friend.

The cabin delivers the essentials and nothing more — a cozy bed, a kitchen with a propane stove and cooking/eating supplies, a wood-burning stove for warmth, and an outhouse. There’s also a solar-heated shower and non-potable running water in the kitchen, though they’re only available from spring to fall.

Check Availability — Airbnb

Green Mountain Modern House

Green Mountain Modern Home

Why you should stay here: A unique, contemporary home in the heart of Green Mountain National Forest.

  • Sleeps: 6
  • Minimum stay: 2 nights
  • Pets allowed: Yes

Situated in the heart of Green Mountain National Forest about 10 minutes from Stratton, this modern home delivers spectacular views and convenient backcountry access. 

In addition to the stellar wall of windows on the back of the house, this modern home features polished concrete floors with radiant heat, a fully stocked kitchen, luxury bathrooms, and toasty sauna. There’s a jacuzzi and fire pit outside, and plenty to do indoors between the pool table, dartboard, and 60-inch TV.

There’s room for up to six guests, and you’re welcome to bring your pup along for the adventure.

Check Availability — Airbnb

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