- Obstetricians & Gynecologists, Great Barrington - Ob-Gyn Doctors, Physicians & Surgeons (Obstetrics & Gynecology)
- Occupational Health Care Professionals, Great Barrington
- Occupational Therapy, Great Barrington - Occupational Health Specialists
- Office Supplies, Equipment & Office Furniture Stores, Great Barrington
- Oil Burners Services, Great Barrington
- Ophthalmologists, Great Barrington - Eye Doctors, Physicians & Surgeons (Ophthalmology)
- Optical Stores - Eyeglasses, Lenses & Sunglasses, Great Barrington
- Opticians, Great Barrington
- Optometrists, Great Barrington - Eye Doctors, Physicians & Surgeons (Optometry)
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- Orchard Service, Great Barrington
- Ornamental Nursery, Great Barrington
- Ornamental Nursery Services, Great Barrington
- Orthodontist, Great Barrington - Teeth Straightening, Invisalign & Dental Braces
- Orthotics and Prosthetics, Great Barrington
- Other Building Materials & Supplies, Great Barrington
- Outdoor & Lawn & Garden Equipment Repair & Service, Great Barrington
- Outdoor Equipment & Accessories, Great Barrington
- Outdoor Furniture & Patio Furniture, Great Barrington - Garden Furniture Stores
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