Holiday houses in Bennington

Guesthouse in North Bennington

An outdoor seating area features two black lounge chairs positioned beside a small table, all set against a backdrop of trees displaying autumn foliage. Potted plants are placed nearby, and a wooden deck extends from the building, creating a seamless connection to the natural surroundings.

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

4.99 out of 5 average rating, 365 reviews

4.93 out of 5 average rating, 105 reviews

A well-lit bedroom features a spacious bed dressed in grey bedding with orange accent pillows. Natural light enters through a skylight, illuminating the wooden floor. A bedside table is positioned beside the bed, accompanied by a woven basket and a door leading to another space.

Apartment in Bennington

Cozy Loft steps from VT Downtown

This third floor loft apartment is walking distance from Historic Old Bennington and the downtown proper. Enjoy local shops and restaurants. Located a few minutes from the highway, giving you access to any number of ski slopes. This space offers high vaulted ceilings, sky lights and modern furnishings. A large bay window sitting area for plenty of natural light and a private balcony with views of Mount Anthony and the Monument. The space also has fiber Wi-Fi internet, Chromecast - YouTubeTV.

4.98 out of 5 average rating, 258 reviews

A charming cottage is set in a green, open yard, surrounded by tall trees. A white fence encloses the property, with a small flowerbed in front. A rustic red barn is visible in the background, complementing the tranquil rural setting.

Farm stay in Bennington

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.

4.96 out of 5 average rating, 100 reviews

A post & beam cabin is presented amid a lush forest setting, featuring a wrap-around deck that extends outwards. Tall trees frame the structure, and a gravel path leads to the entrance, inviting guests into a peaceful retreat surrounded by greenery.

Cabin in Bennington

Mount Anthony Cabin

This post & beam cabin is tucked into the forest at the base of Mt. Anthony. Surrounded by woodlands and adjacent to a 300-acre Christmas tree farm, this cozy cabin offers peaceful seclusion while located only 10 minutes from downtown Bennington. Enjoy a meal on the wrap-around deck or drive a few miles into town where you can find local restaurants and breweries. Step outside for numerous hiking and walking opportunities, or explore the historical and cultural sites Bennington has to offer.

4.99 out of 5 average rating, 100 reviews

A light-filled kitchen features modern appliances, including a vintage-style refrigerator. White cabinetry complements a wooden countertop. The open layout connects to a living area, where a cozy blue chair adds a pop of color. Large windows allow natural light to brighten the space.

Guesthouse in Bennington

Guest Cottage - Mountain Views, History & Hiking

Stay in a newly renovated cottage in the heart of Old Bennington, at the oldest frame house in Vermont! Overlooking a 3-acre yard with mountain views, enjoy New England foliage/skiing/hiking and history steps away. The Bennington Monument, First Church, Robert Frost's grave, and the Bennington Museum are 2 mins away, as are Bennington restaurants and shopping. Williamstown, North Adams museums, Manchester shopping and nordic and downhill skiing are all within a scenic 20-25 min drive.

4.88 out of 5 average rating, 153 reviews

A cozy living room features a brick fireplace as a central focal point, complemented by colorful seating arrangements on a warm-toned floor. A small table with a decorative tablecloth displays a notepad and pine cones. Natural light streams through large windows, creating a welcoming ambiance.

Home in Shaftsbury

Quaint One-Story Vermont House with Mountain View

From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

4.93 out of 5 average rating, 137 reviews

The unique dome-shaped structure is composed of iron and cement, surrounded by lush greenery. Large windows create a bright and airy atmosphere, while the greenhouse-style addition at the front enhances the connection to nature.

Dome in Bennington

5BR Rustic Mountain Sanctuary Dome Home

Find connection in this secluded mountainous retreat. Enmeshed in the natural landscape, this space is only accessible via unpaved roads. Even the journey here is part of the adventure. *4WD & Snowtires are needed during winter & early spring due to the possibility of snow or mud* This property requires a lot of upkeep and the steward will likely be onsite during your stay, however the whole house will be exclusively reserved for your booking. This space will rejuvenate & inspire

The historic Gate House is framed by lush greenery and a manicured lawn, set against a vibrant sunset sky. Its stone façade and charming architecture are accentuated by soft lighting that bathes the exterior in warmth, inviting guests to explore the expansive outdoor space.

4.98 out of 5 average rating, 165 reviews

The Gate House--Experience Vermont!

The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.

4.98 out of 5 average rating, 123 reviews

A living area features a stone fireplace with a roaring fire, surrounded by large windows that invite natural light. A circular coffee table rests on a textured rug, while comfortable seating options include an upholstered chair and wooden accent chairs, complemented by soft lighting.

Cottage in Bennington

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).

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

5.0 out of 5 average rating, 135 reviews

The Vermont Farmhouse|Hiking|Dog Trails|Village

The Luxury of Slowing Down — Vermont Style. Leave the rush behind and feel rested, reconnected and renewed at our dog-friendly, beautifully restored 1860s farmhouse. Wide-plank floors, sun-filled rooms and modern comforts create a warm, impeccably clean retreat. Walk across the road into 280 acres of peaceful Mile Around Woods trails, or stroll into historic North Bennington for cafés and shops. It's all right at your doorstep.

4.92 out of 5 average rating, 202 reviews

Two wooden chairs are positioned on a grassy area, facing a gently sloping hill. A modern white farmhouse is visible alongside a deck with stairs. In the background, trees frame the serene landscape, and mountains are faintly visible under a cloudy sky.

Apartment in Bennington

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.

4.99 out of 5 average rating, 353 reviews

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.

Popular amenities for Bennington holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Bennington

4.98 out of 5 average rating, 301 reviews

An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.

Home in Pownal

Cozy Vermont mini-house

4.82 out of 5 average rating, 150 reviews

A white two-story house sits at the intersection of a quiet street, surrounded by vibrant autumn foliage. A well-maintained yard features a mix of mature trees, with golden and orange leaves contrasting against the blue sky. A leaf-covered path leads toward the entrance.

Loft in Bennington

1 bedroom guest house on dead-end rd

4.99 out of 5 average rating, 100 reviews

A cozy living area features a navy blue sofa adorned with a soft throw, complemented by a glass coffee table. Natural light filters through two windows, highlighting an antique desk and chair. A floor lamp adds warmth to the rustic charm of the oak floors.

Apartment in Bennington

Modern Rustic Hideaway in Town

4.91 out of 5 average rating, 128 reviews

An open living space features high, wooden beams and rustic decor, emphasizing cozy seating arrangements with leather couches. A large American flag hangs prominently on the wall, while a staircase leads to an upper loft area. Natural light filters through windows, illuminating the warm wooden interior.

Home in Shaftsbury

Stylish VT Barn+Guest Fall Favorite+Rare Find

A welcoming entryway features a soft, light-colored bench with yellow accent pillows. Wide plank wooden floors run throughout, and a potted plant adds a touch of greenery. The space is illuminated by a pendant light hanging from the ceiling, with stairs visible in the background.

4.98 out of 5 average rating, 62 reviews

The Old Pine House

Superhost

5.0 out of 5 average rating, 6 reviews

Cozy Mountain Retreat - Museums, Trails & Colleges

4.97 out of 5 average rating, 32 reviews

1865 Farmhouse: mountain, monument & meadow views