Top Villas in Windsor County in 2026

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Top Cities in Windsor County

A coastal landscape with a sandy beach, dense forest, and a clear blue sea under a partly cloudy sky.

Our top choices for Windsor County villas

1. Hakuna Matata - GetAway

Bridgewater Corners

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Top Windsor County Hotel Reviews

Best Western Springfield Hotel

10/10 Excellent

"We had a wonderful stay at this hotel and would definitely recommend it. The property was very clean and well maintained, which made us feel comfortable from the moment we arrived. The staff were exceptionally friendly, welcoming, and always willing to help with any questions or requests. We also appreciated the complimentary drinks and fresh fruit, which were a thoughtful touch. Breakfast has a good variety of options to choose from. Another highlight of our stay was the indoor pool, which was clean, relaxing, and very enjoyable. Overall, this hotel exceeded our expectations, and we would be happy to stay here again."

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"There was a lot to love about Holiday Inn Club Vacations Mount Ascutney, especially for a larger family or group. Our three-bedroom villa was BY FAR the largest accommodation of our trip and surprisingly affordable. We had tons of room to spread out, a decent-sized kitchen for cooking, and FREE laundry—a huge win during a long road trip! The villa kitchen was helpful but pretty minimally stocked. Cooking utensils and cutting boards were lacking, so bring some basics if you plan to cook. Grills are available, but you’ll need charcoal. I’d recommend buying it and any groceries before arriving because the onsite marketplace is expensive. The biggest disappointment was the pool, which is closed through 2027. Traveling with kids, that was a major bummer and definitely something families should know before booking. The location is incredibly beautiful, tucked away on a Vermont mountainside, but it is truly in the middle of nowhere. Come prepared! Overall, the incredible amount of space and affordability made it work really well for our group. It wasn’t our favorite stay of the trip, but the value for a three-bedroom villa was hard to beat."

On The River Inn

10/10 Excellent

"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."

The Quechee Inn at Marshland Farm

10/10 Excellent

"Our stay was wonderful. Staff greeted us with a friendly hello and checked us in while explaining all we needed to know about our room and the property. Room was well appointed and very clean and comfortable. We especially enjoyed visiting with friends on the upstairs porch in the evening. Breakfast was amazing! Resort quality as opposed to the hotel breakfasts we experienced on the rest of our trip. We can’t wait to return."

The Shire Woodstock

8/10 Good

"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer."

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Top Cities in Windsor County

Cavendish

Our top choices for Windsor County villas

1. Hakuna Matata - GetAway

Find vacation rentals that suit your style

Top Windsor County Hotel Reviews

Best Western Springfield Hotel

Align Inn Vermont

Hotel Coolidge

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

On The River Inn

The Quechee Inn at Marshland Farm

The Shire Woodstock

Sleep Woodstock Motel

Lincoln Inn & Gallery

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