Top Farmstay in Windsor County in 2026

A river flowing through a forest with autumn foliage.

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Our top choices for Windsor County farmstays

A red wooden house with a gabled roof, surrounded by snow and trees.

1. Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains

Andover

Aaron L.

A kitchen with a wooden island, stainless steel appliances, and a view of the outdoors through a window.

2. Historic 150-year-old farmhouse, Jacuzzi included

Chester Depot

Hilary C.

AED 1,798 total

includes taxes & fees

27 Oct - 28 Oct

A large, two-story house with a wrap-around porch, large windows, and a chimney.

3. Great Ski or Summer Rental - 5 miles to Okemo/Ludlow, 25 Gorgeous Acres

Ludlow

Bart S.

4. 5 miles to Okemo/Ludlow, 25 Acre Playground, Great Ski or Summer Rental

Cavendish

Irina D.

A house with a red door, white window frames, and a stone pathway leading to the entrance.

5. Barn Hollow Farm - Peaceful four bedroom farmhouse in Barnard, VT

Barnard

Anonymous traveler

A snow-covered landscape with a house illuminated by warm lights.

6. 3 bdrm Stillwater Farmhouse near 4 ski resorts

Weston

Matthew T.

A two-story house with a front porch, a gravel driveway, and a stone wall.

7. Historic 1789 Luxury Farmhouse near Dartmouth College

Hartford

A two-story house with a snow-covered roof and a car parked in front.

8. Cozy Hartland Farmhouse: Mins to Woodstock, Killington & Dartmouth Skiing

Hartland

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Top Windsor County Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

8/10 Good

"Everything about this property was exceptional, EXCEPT the bed. We had an amazing time, enjoyed the lift to view fall colors & mountain coaster. But we had a miserable experience sleeping. The beds are like rock. I know it's the granite state, but get some toppers!"

On The River Inn

10/10 Excellent

"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."