Photo by Rachel Samanyi
Cottages in Windsor County
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Our top choices for Windsor County cottages
1. Addie's Place: A Quiet and Quirky Guesthouse
Addie's Place: A Quiet and Quirky GuesthouseHartford
9.6 out of 10, Exceptional, (19 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
Victor R.
The price is SAR 488
SAR 874 total
includes taxes & fees
27 Oct - 28 Oct
2. Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.
Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.Norwich
10.0 out of 10, Exceptional, (13 reviews)
"This is a wonderful place. Every detail is perfectly considered and the property is immaculate and extremely well appointed. The hosts are gracious and considerate. Great location. Will absolutely be back. Highly recommended!"
Rob P.
3. Woodstock Village Carriage House
Woodstock Village Carriage HouseWoodstock
9.6 out of 10, Exceptional, (117 reviews)
"The carriage house had everything we needed for our visit. It was perfect and would definitely stay here again."
anthony
4. Cozy Historic Hilltop Cottage with Mount Ascutney View
Cozy Historic Hilltop Cottage with Mount Ascutney ViewWest Windsor
9.6 out of 10, Exceptional, (88 reviews)
5. Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Cozy cottage on the river, minutes from skiing, horse events, and so much more!Reading
9.8 out of 10, Exceptional, (22 reviews)
"We loved the place and will stay again"
Michelle
6. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8Cavendish
10.0 out of 10, Exceptional, (2 reviews)
The price is SAR 669
SAR 2,032 total
includes taxes & fees
4 Nov - 5 Nov
7. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Ludlow Cabin on Lake Pauline w/ Outdoor Fire PitLudlow
The price is SAR 560
SAR 1,121 total
includes taxes & fees
23 Oct - 24 Oct
8. Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!Chester
10.0 out of 10, Exceptional, (2 reviews)
"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
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor County Hotel Reviews
Jackson Gore Village, A Vail Resorts Property
10/10 Excellent
