Woodstock Vacation Homes

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

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Our top choices for Woodstock holiday homes

A charming 1820's farmhouse

Woodstock

Robin H.

HK$11,446 total

includes taxes & fees

27 Jan - 28 Jan

Off Grid Glamping Shed with River Access

Randolph

HK$729 total

includes taxes & fees

26 Jan - 27 Jan

Game Room, Fireplace & Pet Friendly - Top of the Hill

Quechee

Maryanne C.

HK$4,804 total

includes taxes & fees

29 Jan - 30 Jan

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish

Maya T.

HK$2,494 total

includes taxes & fees

27 Jan - 28 Jan

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Killington

denise k.

HK$2,519 total

includes taxes & fees

28 Jan - 29 Jan

Luxury Condo Tucked in the Heart of Killington

Killington

Marjana

HK$2,821 total

includes taxes & fees

27 Jan - 28 Jan

Charming Lakefront Cottage on Lake Mascoma

Enfield

Anne S.

HK$4,535 total

includes taxes & fees

28 Jan - 29 Jan

Large Killington Area Home | Sleeps 7 | Game Room

Bridgewater

Owen C.

HK$4,890 total

includes taxes & fees

26 Jan - 27 Jan

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Mendon

Aurore H.

HK$2,387 total

includes taxes & fees

29 Jan - 30 Jan

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Killington

Catherine S.

HK$4,943 total

includes taxes & fees

26 Jan - 27 Jan

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

HK$4,605 total

includes taxes & fees

26 Jan - 27 Jan

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Rutland

HK$3,290 total

includes taxes & fees

2 Feb - 3 Feb

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow

Edwin G.

HK$3,573 total

includes taxes & fees

28 Jan - 29 Jan

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

HK$4,605 total

includes taxes & fees

26 Jan - 27 Jan

Killington Retreat | Deck-Fire Pit-Mountain Views!

Clarendon

Thaddeus T.

HK$3,040 total

includes taxes & fees

1 Feb - 2 Feb

180-degree panoramic views of Vermont's mountains from the living room and Deck

Hartford

"The house was absolutely beautiful. A unique mix of modern and 70’s. The layout was spot on . We were only there one night , a very quick stop over but it was so comfortable and cozy. The host was so easy to communicate with and was very accommodating. Plenty of room to sleep a large group and the views….you have to see in person. Stunning . I travel a lot and use VRBO for all of my travels. This was one of the best experiences I have had . I recommend 100%. "

Mary Anne C.

HK$3,824 total

includes taxes & fees

26 Jan - 27 Jan

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne

"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...

Essa R.

HK$4,867 total

includes taxes & fees

26 Jan - 27 Jan