Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

The Old Academy, stay in a part of history.

Bedrooms 4
Half Baths1
Space 3,000 sq ft
Property type house
Minimum Stay 2 - 3 nights


About the property

Located along the beautifully tree-lined historic Monument Avenue, in the village of Old Bennington, The Old Academy stands proudly. While the residence itself dates back to 1821, it was renovated to have all of the 21st century features that one could want. Stainless steel appliances, crown molding, two fireplaces, granite counter tops, hardwood floors, and an open floor plan greet those who enter the home. Central air and a brand new heating unit (2017) allow for comfortable control of the climate no matter what time of year it is. A large ensuite bathroom, complete with rainfall shower head, makes the master bedroom a sanctuary of relaxation.A large third story loft area provides room for extra company. This four bedroom, two and a half bath home is the perfect residence for rental at any time of the year.

The Old Academy is located one block away from the Bennington Battle Monument and the Old First Church. Historic homes fill the area with a sense of both prestige and preservation. The village of Old Bennington is surrounded by lush green mountainsides, waterfalls, and hiking trails.

Situated on the most historic avenue in Vermont, the Old Academy

was constructed in 1821 to be “the finest building in the state.” According to the National Register of Historic Places, it is also one of the most architecturally significant buildings in the area. The Old Academy served as a private school, public school, and later, the Bennington public library. Famed Vermont artist, Warren Kimble, featured the Old Academy in a painting that has been

included in his books and calendars. In the 1990s, the building was

completely restored and converted to residential use.

The house is on city water and has propane heat. It has forced-air

heat and air conditioning, separate electronic dampers between

floors, two working fireplaces, crown moldings, recessed lighting on dimmers, electronic air filtration, a full basement, and a third-

floor loft with bedroom and sitting areas and a thermostatically-

controlled whole-house fan.

In the garden there is mature well-tended landscaping, a fully-

automatic irrigation system, bluestone walks and terraces, stone

walls, a picket fence, and a crushed-stone driveway.

More Details

Property Manager
James Gallen
Member since: 2018
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
September 19, 2018


Old Bennington House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 3000 sq ft
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 8
  • Children welcome
  • Parties/events not allowed
  • Non smoking only
  • Please remove outside shoes upon entering the house.
  • Please do not rearrange the furniture or decorations.
  • Please do not bring more than two cars to the house.
Location Type:
  • Monument View ...
  • Historic
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Fireplace ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Parking Off Street
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kettle
  • Kitchen
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • 1 Half Bath
  • Master Bath - toilet , tub , shower
    Downstairs Half Bath - toilet
    Guest Bathroom - toilet , combination tub/shower
  • 4 Bedrooms, Sleeps 8
  • Guest Room 1 - 1 queen
    Loft - 1 double , The loft is located on the third floor. It also has a sofa.
    Guest Room 2 - 1 queen
    Master Bedroom - 1 king , An en suite bathroom is part of the Master Bedroom.
  • Games ...
  • Satellite / Cable
  • Television ...
  • Golf ...
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • wheelchair inaccessible ...
  • churches
  • festivals
  • museums
Leisure Activities:
  • bird watching
  • horseback riding
  • outlet shopping
  • photography
  • scenic drives
  • sight seeing
  • sledding
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
Sports & Adventure Activities:
  • cross country skiing
  • cycling
  • golf
  • hiking
  • hunting
  • ice skating
  • mountain biking
  • skiing
  • snowboarding
  • snowmobiling


4.8/5 -
(5 traveler reviews)

80% Complete
20% Complete
0% Complete
0% Complete
0% Complete
The Old Academy, stay in a part of history.
average rating of 4.8 based on 5 reviews

Historical charm with Current Amenities

  • 5 of 5

My family had the best experience at The Old Academy! James was there to meet us and go over the layout/amenities of the historical schoolhouse turned family home. The open floor plan on main level was perfect for keeping an eye on my young kids, while also enjoying company of my extended family. Having central air in Vermont is a rare find & certainly made our stay more comfortable! The owners provided great quality, clean linens & towels, along with toilet paper - all of which we brought too but was nice to have extra! A short walk to Bennington Monument and quick drive to quaint spots in downtown Old Bennington gave us plenty of options of things to do. I would absolutely recommend staying here and certainly will do so myself if we are in the area again! Thank you James for sharing The Old Academy with us!

  • Submitted: Jul 30, 2018
  • Stayed: July 2018
  • Source: HomeAway
Did you find this review helpful?
0 0
San Jose, CA

Nice place to stay

  • 4 of 5

We enjoyed our stay. Thanks James.

  • Submitted: Jul 27, 2018
  • Stayed: July 2018
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

We had a fantastic experience at this amazing property! Highly recommend!

  • 5 of 5

Our family was fortunate to stay at the historic Old Academy during the week of July 4th, 2018, surrounded by history and multiple opportunities for fun, including a reading of the Declaration of Independence in the shadow of the Bennington Monument.

James was a wonderful host and the accommodations exceeded our expectations. The common space was great for the entire family and our visitors. The bedrooms, bathrooms, second floor library/sunroom, and third floor loft were all well-used by our crew and luxurious. We enjoyed cooking in the well-appointed kitchen. It was handy to have use of the washer and dryer as we did lots of biking, running, hiking, swimming and general outdoor activity. The grounds were stunning, especially the shade garden behind the home. It was the perfect spot for morning coffee, a cookout and evening cocktails. We enjoyed Bennington, the Battenkill River and the Alpine Slides at Bromley Mountain. Overall top rating!

  • Submitted: Jul 23, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
Owner's Response: Monica, Thank you so much for your kind and descriptive review. You made me want to stay at the house myself! We are honored to host you and your family, and I am extremely happy that you enjoyed The Old Academy so much. Please come back anytime to our beautiful and peaceful part of the country!
Did you find this review helpful?
0 0
Chadds Ford PA

Comfortable and Convenient

  • 5 of 5

James was so easy to work with and The Academy was clean and comfortable. All cotton bedding and thick towels!

  • Submitted: Jul 16, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
Owner's Response: Sally, Thank you for choosing to stay at The Old Academy. We enjoyed hosting you and your family during your vacation to our beautiful area.
Did you find this review helpful?
0 0

Excellent house in VT

  • 5 of 5

Our family just spent 10 nights @ this great property in Bennington, VT. The house was in great shape and the owner was extremely helpful with all our requests. We would highly recommend to anyone.

  • Submitted: Jun 25, 2018
  • Stayed: June 2018
  • Source: HomeAway
Did you find this review helpful?
0 0


Nearest Airport
37.9 Miles
Albany International
Nearest Golf
0.2 Miles
Mount Anthony Country Club
Car: necessary

Within two blocks of The Old Academy, there are the Bennington Battle Monument, the Old First Church (where Robert Frost is buried), and the Bennington Museum.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $100
Refundable Damage Deposit $1,000

Manager's Cancellation Policy

  • 50% refund if canceled at least 14 days before arrival date.
  • 100% refund if canceled at least 30 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

You might like these similar properties