Holiday rentals in Bennington County

The House of Pi

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Country Colonial Home with rolling fields & stream

This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.

The Farm Cottage- Quiet 1BR on Hobby Farm

Welcome to our peaceful 1-bedroom cottage on a small hobby farm, perfect for couples or solo travelers visiting the Bennington area. This cozy space is designed for rest and simplicity. Whether you're in town visiting family, exploring local trails, or just passing through for a few days, you’ll have a comfortable place to unwind and recharge. Thoughtful touches like fresh eggs from our chickens and homemade jams await you, while the cozy setup makes it easy to settle in and feel at home.

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Serene & Stylish Chalet w/ HOT TUB near Manchester

Hey there, relaxation enthusiasts and adventure seekers alike! Shady Pines Chalet is your spot: a groovy 4-bed/2-bath cabin tucked away in the lush, serene embrace of the Green Mountains! It's just 15mins from Manchester, where you can shop and dine like a pro. Plus, you're in prime adventure territory: hiking, kayaking, & fly-fishing are all on the menu. And if you're a winter warrior, Bromley (25min) and Stratton & Magic Mountains (40min) are ready for your skiing prowess!

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Rollin Cottage

Welcome to Vermont! Rollin Cottage is a country cottage in a rural setting not far from the Village of North Bennington with a babbling brook, private patio and cottage gardens. Full kitchen, two bedrooms, ground floor master bedroom plus private loft bedroom with an additional sofa bed (full) in the living room. All amenities are provided.

Quiet Getaway in Equinox Valley

Private 1-bedroom apartment in a mountain setting. Just south of Manchester Village at the base of Little Equinox Mountain. Drive by a small dairy farm and up a country lane to a second-floor walk-up with mountain view. Close to Manchester Designer Outlet shopping, restaurants, wedding venues, hiking, biking, fishing and more.