- Obstetricians & Gynecologists, Bennington - Ob-Gyn Doctors, Physicians & Surgeons (Obstetrics & Gynecology)
- Office Buildings & Parks, Bennington
- Office Supplies, Equipment & Office Furniture Stores, Bennington
- Oil Burners Services, Bennington
- Oil Change & Lubrication, Bennington - Auto Oil & Quick Lube
- Old Age Homes Service, Bennington
- Oncologists, Bennington - Cancer Doctors, Physicians & Surgeons (Oncology)
- Optical Stores - Eyeglasses, Lenses & Sunglasses, Bennington
- Opticians, Bennington
- Optometrists, Bennington - Eye Doctors, Physicians & Surgeons (Optometry)
- Oral Surgeon, Bennington - Dentists - Oral & Maxillofacial Surgeons
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- Ornamental Greenhouses, Bennington
- Ornamental Nursery, Bennington
- Ornamental Nursery Services, Bennington
- Orthopedic & Prosthetic Appliances & Shoes, Bennington - Orthopedic Shoes
- Other Building Materials & Supplies, Bennington
- Other Lodging, Bennington
- Other Office Supply Stores, Bennington
- Outdoor & Lawn & Garden Equipment Repair & Service, Bennington
- Outdoor Equipment & Accessories, Bennington
- Outdoor Furniture & Patio Furniture, Bennington - Garden Furniture Stores
- Oxygen & Respiratory Equipment & Supplies, Bennington - Oxygen Concentrator, Tank, Machine, etc
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