Vacation rentals in Bennington

Guest suite in Shaftsbury

4.99 out of 5 average rating, 164 reviews

Peaceful Get Away at Birds of a Feather Farm

Our cozy upstairs studio can accommodates up to 4 and is separate from the main house. Plush towels, linen, pillows and blankets. Kitchenette is fully stocked with everything you need for cooking. The private entrance is equipped with punch key lock to facilitate easy self check-in. A queen size sleep number bed, queen size pullout couch, table with four chairs, a dresser, one bathroom with shower, smart TV and WIFI. Heat and cooling. Spa services are available. For Booking & Fees contact host.

4.92 out of 5 average rating, 183 reviews

Escape the City- Vermont Studio

Our studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Grn. Mtn. National Forest. It's on the second floor of our home (above the garage) through a private entrance with a personal deck and outdoor seating. Take an afternoon stroll to the Mile Around Woods, or day hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Guesthouse in North Bennington

4.99 out of 5 average rating, 252 reviews

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 animal

4.99 out of 5 average rating, 268 reviews

Cabin in Shaftsbury

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!

4.98 out of 5 average rating, 174 reviews

Farm stay in Bennington

The Farm cottage

Take a break and unwind at this little peaceful oasis. A little bit of the country is right beside you with the neighing of horses and the clucking of chickens who roam our property. We are close to Bennington College and great restaurants and Robert Frost house. We are 35 minutes from Manchester that has some great restaurants and shopping. Bromley ski resort is just beyond Manchester in Peru Vermont . It is a year around resort with water slides in summer and skiing in winter .

4.94 out of 5 average rating, 1,269 reviews

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

4.98 out of 5 average rating, 692 reviews

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.

4.95 out of 5 average rating, 165 reviews

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.

4.98 out of 5 average rating, 136 reviews

Home in Bennington

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.

4.95 out of 5 average rating, 221 reviews

Farm stay in Hoosick

Airbnb @ Sweet & Savory Farmette

Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.

Farm stay in Johnsonville

4.98 out of 5 average rating, 323 reviews

Overlook at Graceful Acres Farmstay

Enjoy the grace of a historic family farm in the heart of eastern NY. Let the cool, fresh air and sounds of the outdoors start your day. Fill your time with a hike across our 440 acre farm then spend time with the animals and learn more about regenerative farming during a scheduled farm tour. Graceful Acres Farmstay is situated an hour south of the Adirondack State Park and within 35 minutes of Saratoga Springs, Albany, Troy, NY and Bennington, VT.

4.99 out of 5 average rating, 292 reviews

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.

Vacation rentals for every style

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Popular amenities for Bennington vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Bennington

4.97 out of 5 average rating, 91 reviews

Suite Sunset 311 Rice Lane Bennington VT

EllenRating, 5 stars1 month ago

George went about and beyond! We arrived to find a beautiful basket of fruits and bagels and cream cheese in the refrigerator. We were only there for one night but I wish we could have stayed longer to have had a chance to relax in such a spacious accommodation. Looking forward to returning.

5 out of 5 average rating, 52 reviews

Guesthouse in Arlington

guest house with attention for detail

StephanieRating, 5 stars3 days ago

It's home away from home! Everything we needed was available. Dianne and John were quick to respond to any questions or concerns. The layout was beautiful with lots of attention to detail. We would definitely stay again if they'd have us.

4.86 out of 5 average rating, 130 reviews

Home in Shaftsbury

Quaint One-Story Vermont House with Mountain View

BruceRating, 5 stars2 weeks ago

This is a great place to stay convenient to Bennington, Manchester and Brattleboro plus Williams and the Clark Museum and it’s a quick drive to a great coffee shop in North Bennington Pangaea which has homemade donuts on Sunday mornings.

5 out of 5 average rating, 29 reviews

Cottage in Eagle Bridge

The Crik House: modern digs, American farm country

MattRating, 5 stars2 weeks ago

We really enjoyed out stay and hope to return again in the future. The place had great light and was just a very peaceful place to hang out and relax. Its a beautiful area and we found some great food and beer and was also enjoyed cooking at home and enjoying the home. The owner was very accommodating and had great communication throughout our stay... I would highly recommend it for anyone looking to stay in the area.

4.98 out of 5 average rating, 49 reviews

Awesome 3 Bedroom Apartment Close to it all

RosaRating, 5 stars1 day ago

Staying at Theodore's house is like being at home. The house is very big and well furnished. There are also plenty of interesting books. It is well located and Theodore is really a nice person. We appreciated a lot the local food (cheese, water, etc) that he gifted us. We definetly recommend him.

4.99 out of 5 average rating, 90 reviews

Cottage in Bennington

Cozy, bright 3-bedroom Cottage with fireplace.

DanielRating, 5 stars1 week ago

Absolutely lovely home and setting. One of the most tastefully furnished and decorated Airbnbs we've stayed in. True Vermont luxury and a welcoming array of treats and amenities.

5 out of 5 average rating, 29 reviews

Home in Woodford

Bright airy cottage w/ lake view

VickiRating, 5 stars2 weeks ago

We had a great time at the Chickadee over Memorial Day weekend! The weather wasn’t totally in our favor so sadly we couldn’t enjoy the nearby lake, but we filled our time with short trips into Bennington and Wilmington. The sunroom is a great spot to relax and the beds are super comfy! We were bummed that the outdoor shower had broken right before our stay, but Sarah did her best to try to get a handyman out and offered us a small discount when it couldn’t be fixed. We’ll just have to come back another time to enjoy all of the outdoor amenities!