SLEEPY HOLLOW FARM- To visit Vermont in the Fall was a dream of mine. I am so happy that I was able to do just that this year. One of the places I visited was this photographic icon in rural Vermont, the Sleepy Hollow Farm, near Woodstock. Well known by most photographers the Sleepy Hollow Farm is the place to be if you want to get that perfect classic Autumn shot and an early morning light is best to be there to capture rich deep autumn colours. Rumors has it that it was once owned by Joe Perry of Aerosmith. Perry and his wife of 30 years, Billie, bought the property and they'd often bring their horses there from their home outside Boston. #ilovermont #ScenesofNewEngland #vermontbyvermonters #colorful #autumn #fall #roadtrip #travel #adventure #fallfoliage #historic #vermont #Bestof5

Photo by Rachel Samanyi

South Pomfret house rentals

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February 2026

March 2026

Explore South Pomfret house rentals

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Sleeps 8 · 3 bedrooms · 2 bathrooms

Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

Sleeps 12 · 5 bedrooms · 3 bathrooms

Luxe Quechee home on quiet road - chef’s kitchen, two-car garage, screened porch

Sleeps 7 · 3 bedrooms · 2+ bathrooms

Top rated house rentals - South Pomfret

Image of Classic Vermont Farmhouse in the Heart of Woodstock - close to skiing

Clean, comfortable, convenient.

Great experience. Check in was easy; house was super clean. Nice grounds and privacy. Great location close to Woodstock town and xc skiing. Comfortable beds, kitchen, living room. Very conducive to family time. All around excellent stay.

Jessica R.

Stayed Feb 2024

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Explore South Pomfret house rentals

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Next to Saskadena Ski, Great Views - Half Past Six

Walk to S6! Pool Table/Fireplace - Saskadena Lodge

Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

Only Steps to S6 - Saskadena Lodge & Little House

Luxe Quechee home on quiet road - chef’s kitchen, two-car garage, screened porch

Top rated house rentals - South Pomfret

Clean, comfortable, convenient.

Find spaces that suit your style

Peace of mind

More quality time

All the privacy of home

More for less