Bennington College draws a lot of young people to the region, but the greatest lure of all is perhaps the natural beauty that characterizes The Shires of Vermont. Beyond the region's prodigious natural beauty, Bennington also boasts excellent arts, cultural, and dining experiences. Start with The Apple Barn and Country Bake Shop for apple cider donuts, and head over to Bennington Potters to shop for handmade pottery.
You can catch a show in the evening at the Oldcastle Theatre Company and check out the Laumeister Art Center at Southern Vermont College with the Vermont Covered Bridge Museum, and learn why the region is known for its historic covered bridges. Check out The Dollhouse and Toy Museum of Vermont, or swing by Vermont Distillers in Wilmington for a sample. There's something in The Shires near Bennington to satisfy every interest and taste.
You can't miss a visit to the Bennington Museum, which is home to the largest collection of Grandma Moses paintings in the world, along with other exhibitions of contemporary and outsider art, military history, and works from the Gilded Age. You can browse local arts and crafts in historic downtown Bennington at quaint stores like Fiddlehead at Four Corners. History lovers should also check out the Revolutionary War site of the Bennington Battle and a well-preserved Victorian-era mansion: Park McCullough House.
The Robert Frost Stone House is also nearby, under ownership of Bennington College. Wander the surrounding forest and see if you can find where “two roads diverged in a yellow wood.” The beautiful Vermont woodland just outside his dining room inspired one of his most famous poems, "Stopping by the Woods on a Snowy Evening." Come see the homestead of one of Vermont's most famous native sons, from apple orchards to the stone barn.
Come to fish, hike, bike, ski, or to eat a slice of real Vermont apple pie. Come to The Shires and Bennington, and you'll discover so much more than southern Vermont — you'll get an authentic taste of America.
When is it an ideal time to visit Bennington, VT?
Bennington is a destination for all seasons. Whether you come to ski, shop, or hide away in a favorite hotel for a romantic weekend, you'll find plenty of activities. But don't count Bennington out for all-weather fun. Summers feel just right, averaging in the low 80s. June and July are the rainiest months of the year in Bennington, so plan accordingly. Spring and fall are just as pleasant, but cooler, in the 40s to the mid-50s. Winters do get frigid in the 30s, with some precipitation.
Bennington Battle Weekend takes place in late August, commemorating the Revolutionary War-era Bennington Battle. The town throws a huge party over a long weekend, complete with barbecues, silent auctions, car cruises, kids' activities, and a 5K Road Race, all leading up to Sunday's living history encampment at the Bennington Battle Monument. Take a guided tour of the grounds, then prepare for a tastier battle: The Battle of the Pies on Main Street. You must sample the apple pie, which is the official pie of the state of Vermont (made with the official fruit!).
The annual Southern Vermont Garlic and Herb Festival has been an August tradition for over 23 years. You can sample garlic-inspired, herb-laden goodies from hundreds of vendors, while you check out local goods and entertainment. It's the perfect family getaway, with activities like face-painting, bounce houses for the kids, and a beer and wine garden for mom and dad.
Below is a chart of the current pricing seasonality of hotels and motels in Bennington, VT:
Bennington, VT: Prices by Star Rating Class
Below are 3 charts illustrating avg. price trends by star rating class in Bennington, VT. Browse these illustrations to evaluate the best dates to book a room in Bennington throughout the year.
Where are the luxury hotels near Bennington, VT?
4 Star Average Prices: $173.16
You will feel pampered and revitalized after a stay at the Equinox, a Luxury Collection Golf Resort & Spa, Vermont in Manchester. This gracious Colonial-style resort is as beautiful as the surrounding countryside, which includes the Equinox Preservation Trust. Just over 5 miles from Bennington, the Equinox is grandly decorated in New England style, from the wood-beamed ceilings to the palatial seating and dining areas.
This luxury hotel boasts four restaurants on-site in addition to a spa, golf course, indoor pool, and the adjacent land of the Equinox Preservation Trust. Guests enjoy shuttle service throughout 2 miles of the property, making a quick day trip into Manchester Village easy. Wedding services and romantic perks like an outdoor fire pit make this the hotel of choice for a Southern Vermont destination wedding.
Are there affordable hotels in Bennington, VT?
3 Star Average Prices: $157.70
Looking for paradise in Southern Vermont? You'll find it at Paradise Inn. This property feels like a serene getaway in The Shires, and yet historic downtown Bennington is also conveniently walkable from the property. Paradise Inn guests will be delighted to discover private balconies overlooking the outdoor seasonal pool. Inside, cozy bedding invites you to rest before conquering the trails the next morning. You can relax and check your email using the free wireless internet connection. Freshly brewed complimentary coffee will wake you up in no time.
You'll find excellent rates at the Green Valley Motel in Williamstown, just over the state line in Massachusetts. Full of charm and character, the Green Valley Motel offers guests top-level service and a cozy room in a lovingly maintained property, situated just 12 miles from Bennington and surrounded by the stunning vista of the Berkshires. Guests can indulge in a free daily continental breakfast, plus perks like cable programming and fast, free wireless internet connectivity. This motel has ample parking space for RVs, and it's pet-friendly, too.
2 Star Average Prices: $130.93
What are the best hotels with discounts in the Bennington area?
If you're looking for discounts on your stay, the Hampton Inn Bennington is a great choice, with both AAA and senior citizen discounts. You can enjoy a complimentary hot and cold breakfast to start your day, and stay connected with wired or wireless internet. The Howard Johnson by Wyndham Williamstown is another great option for savvy travelers, with discounts available for seniors, AAA members, and members of the armed forces. This is a great hotel for travelers who like to spend time outdoors — take advantage of the outdoor pool, barbecue grills, and a picnic area.
What value hotels are in Bennington?
If you want to be close to all the sites of Bennington for an affordable rate, check out Best Western Bennington. This roadside hotel offers great value, from the guest rooms to the free daily breakfast service. Combination tubs and showers are stocked with free toiletries, and you can leave your hair dryer at home because each guest room comes stocked with one for your convenience.
Relax and unwind, lounging on the bed while watching cable programming on the flat-screen television, or log onto the free wireless internet connection to check your email. Guests also enjoy access to a seasonal outdoor pool and in-room use of a mini-fridge and microwave.
Where can you go to enjoy the outdoors in The Shires of Bennington, VT?
There are plenty of ways to enjoy the outdoors in Bennington, whether you prefer a leisurely stroll or relaxing afternoon birding, or something more adventurous like a zip line experience at Bromley or a mountain biking excursion. Bennington is also known for its network of caves, some of which can be explored by experienced spelunkers with guidance from the Vermont Cavers Association. Then, of course, there's winter skiing, snowboarding, snowmobiling, and skating in the Northshire. Mountain bikers and cyclists will discover some of the best trails in New England in this region, starting with the Bennington Area Trail System.
There's no shortage of natural beauty to enjoy in Bennington. Explore the serene woodland of The Green Mountain National Forest or any of the three local state parks. Set out on the Southern Vermont Arts Center's Boswell Botany Trail, and you'll be treated to three-quarters of a mile filled with beautiful orchids, birches, and ferns, all native to the unique glacial microclimate.
Fishing is a huge draw in The Shires. In fact, the modern fly-fishing reel was invented in Vermont. April is fishing season, and you'll find plenty of trout leaping in the Batten Kill, Walloomsac, and Mettawee Rivers. The Appalachian Trail also owes its origins to Vermont. The Long Trail, which stretches from northern to southern Vermont, inspired the Appalachian Trail. You can hike one of the highlights of both trails near Bennington, and the highest peak in Southern Vermont: Stratton Mountain.
The hiking options are endless, and the vistas you'll enjoy along the way strike visitors with wonder, like the breathtaking Lye Brook Falls (over 125 feet tall). The Taconic Crest Trail, starting in nearby New York, leads hikers to a secret crevice where snow stays frozen, even into early summer. Hikers love to sample the fresh blueberries along the trail as they go.
Even Robert Frost might agree that if you take the road less traveled to Bennington, Vermont, you'll discover it makes all the difference. See the beautiful sites and breathe deeply of the clean, crisp Shires air, and your troubles will soon melt away.
FAQs about hotels in Bennington
Recent traveler guest reviews of Bennington, VT
Below are reviews of the city of Bennington, VT from an actual visitor's perspective.
"My hometown"
Score
4.0 / 5
My hometown - always love it here.
Alan D., from 25-Jan-2026
"Cute shops"
Score
4.0 / 5
Dawn M., from 28-Dec-2025
"Location And Excellent Food"
Score
4.0 / 5
I go to Harvest Christian Ministries church here. Had dinner at Chili's which was excellent.
Joseph R., from 12-Nov-2025
"Beautiful city"
Score
5.0 / 5
Beautiful city. Loved Madison Brewery. Enjoyed the Bennington battle monument. Not much traffic.
Cara C., from 11-Nov-2025
"Quaint!"
Score
4.0 / 5
Quaint environment with great places to eat
Stephanie S., from 13-Oct-2025
"Covered bridges and close to my sister's home."
Score
5.0 / 5
Joyce B., from 31-Aug-2025
"Beautiful!"
Score
4.0 / 5
Erin K., from 12-Aug-2025
"Cute Town"
Score
4.0 / 5
Cute town, close to wedding venue!
Kristen C., from 13-Jul-2025
"Lovely City"
Score
4.0 / 5
Bennington is a lovely city with a good hospital.
Denis H., from 30-May-2025
"Great location"
Score
4.0 / 5
Most things. Staff is better than perfect. Food is so-so.. but its the quality not the preparation. Keep the people you have hired, They are perfect. The right amount of humor and dedication.
Ll F., from 19-Feb-2025
"Beautiful Quaint Town & Delicious Food!"
Score
5.0 / 5
A beautiful, quaint town! We are at Lil Britain and the food was delicious!
Carol T., from 10-Oct-2023
"Plenty of places to eat and a good museum."
Score
5.0 / 5
Town of Bennington was fine with plenty of places to eat and a good museum.
James H., from 03-Aug-2023
"Veterans Home"
Score
5.0 / 5
We were visiting a Vietnam vet. at the Veterans Home there.
Dawn M., from 01-Jul-2023
"Quaint!"
Score
4.0 / 5
Quite and quaint!
Donna R., from 29-Jun-2022
"Historic Bennington is a grand small city!"
Score
5.0 / 5
Historic Bennington is a grand small city!
Patricia K., from 23-Jun-2022
"Lots of places to eat, drink and shop!"
Score
5.0 / 5
Lots of places to eat, drink and shop!
Barbara B., from 14-Feb-2022
"Beautiful"
Score
4.0 / 5
Nice New England town with great scenery.
Cassandra G., from 05-Jul-2014
The average traveler rating of the city of Bennington, VT shown above is
4.4 out of 5 based on 17 reviews