Holiday rentals in Bennington

Cottage in North Bennington

Romantic Private Vermont Cottage - Waterfront

Welcome to beautiful Southern VT! This is a private cottage located in Bennington, VT. The setting is picturesque, on a private lake with diverse wildlife, waterfall and covered bridge. Full kitchen, covered porch, loft bedroom and additional sofa bed. We provide every conceivable amenity for a comfortable stay. A unique retreat for a cozy and peaceful getaway. There is no other vacation property of this quality and character in southern Vermont. Enjoy mornings on your own private lake.

Home in Bennington

Bennington Guest Barn 3 Bedrooms

Really sweet 3 complete bedrooms with 1 rollout bed. New & decorated in typical Vermont decor. Many amenities provided to make your stay feel like home. Convenient location: 1 mile to Bennington College, 20 miles to Mass MOCA, Mt. Snow, Jiminy Peak and Bromley are within 30 miles and 8 miles to Cross Country Ski at Prospect Mt. Robert Frost, Bennington Museums along with three unique Covered Bridges are 1 – 3 miles away. Find out why people love Vermont and keep coming back.

22–29 Apr

Guest house in North Bennington

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 light space with 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. Please note that due to a severe allergy, we cannot accommodate animals.

19–26 Jul

Cottage in Shaftsbury

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

11–18 Aug

Cabin in Shaftsbury

The LoveNest -Charming private cabin on 65 acres

The Love Nest has returned! We’re high up on the hill yet close to art and culture, great views, restaurants and dining, family-friendly activities, skiing, Bennington, Manchester VT close by. Williamstown Mass not far. A huge yard. You’ll love my place because of the coziness, the light, the comfy bed, the well equipped kitchen, privacy and views, the extreme quiet and relaxation. Waterfalls! My place is good for couples, solo adventurers, and dog guests. 420 friendly!

11–18 Nov

Flat in Bennington

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

10–17 Jul

Flat 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.

9–16 Sept

Home in Bennington

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.

25 Mar – 1 Apr

Flat in Bennington

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

4–11 Sept