Windsor County Cottages from CA $331

A river flowing through a forest with autumn foliage.

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Top Cities in Windsor County

A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Our top choices for Windsor County cottages

A white house with a red roof and a hammock in the yard.

1. Addie's Place: A Quiet and Quirky Guesthouse

Hartford

Victor R.

CA $331 total

includes taxes & fees

Oct 27 - Oct 28

A two-story house with a snow-covered lawn, a wooden deck, and a garage.

2. Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.

Norwich

Rob P.

A two-story house with a garage, a small porch, and a chimney.

3. Woodstock Village Carriage House

Woodstock

anthony

A deck with a metal chair and a decorative vase, overlooking a forested area with autumn foliage.

4. Cozy Historic Hilltop Cottage with Mount Ascutney View

West Windsor

Paul H.

A red building with a black door, surrounded by a gravel driveway and a wooden fence.

5. Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Reading

Michelle

A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

6. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Cavendish

Mark G.

CA $779 total

includes taxes & fees

Nov 4 - Nov 5

A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

7. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow

CA $426 total

includes taxes & fees

Oct 21 - Oct 22

A cabin with a porch, surrounded by a grassy yard and trees.

8. Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

Chester

"The property was lovely, peaceful, and quiet, surrounded by trees on a quiet country drive. It was the perfect weekend getaway and we really enjoyed sitting on the porch and out under the string lights, watching the sun go down through the trees. The house itself is lovely, cozy, and comfortable. Our hosts were very sweet, everything was very thoughtfully laid out and clean and easy to access. We also loved meeting the goats, Ozzy and Coco, and the chickens! This was such a pleasant stay, I...

Angela

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Top Windsor County Hotel Reviews

Align Inn Vermont

10/10 Excellent

"Room was comfortable. Staff was very nice."

Pointe at Castle Hill Resort

10/10 Excellent

"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want to shop however, one minute up the road is Murdoch’s restaurant and they had delicious food. We ate there twice. Just make sure to make a reservation. All in all it was a nice stay and we definitely suggest staying there."