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 two-story house with a front porch, a garage, and a well-maintained lawn.

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

Chester Depot

Vijay R.

AED 1,462 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Ludlow

Bart S.

3. 5 miles to Okemo/Ludlow, 25 Acre Playground, Great Ski or Summer Rental

Cavendish

Irina D.

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

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

Andover

Aaron L.

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

A brick building with a snow-covered roof and a wreath at the entrance.

9. Charming Vermont Farmhouse & Peaceful Retreat

Springfield

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Top Windsor County Hotel Reviews

Woodstock Inn & Resort

10/10 Excellent

"Fantastic stay at Woodstock Inn this week! The room and property were spotless, and the staff was incredibly kind and welcoming. The spa was beautiful, the food at Red Rooster was excellent, and the athletic center, pool, and hot tub were all great. The entire property has a quiet, peaceful atmosphere that makes it easy to relax and unwind. Would absolutely recommend!"

Lincoln Inn & Gallery

10/10 Excellent

"If you are visiting Woodstock, VT, this is a wonderful place to stay! The location is great- just 5 min from the main strip and easy to get anywhere else. The staff there were very nice, helpful and accommodating. The owner gave us a list of restaurants and cafes to check out in the area as well as recommendations for things to do all of which was really helpful to make the best of our trip! I cannot emphasize enough how wonderful the owner and staff were. They were so friendly! The room was spacious and beautiful and the grounds are gorgeous! It’s right next to a beautiful river, covered bridge and has lots of outdoor space to hangout comfortably. Would definitely recommend as a great place to stay! We will come again!"

Room 1

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