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Winchester Vacation Packages

This was the perfect long weekend get away. The property was fairly quiet given it was the off season. Phone check-in and check-out was lovely, and if you don’t enjoy standard hotel check-in lines, it’s even better. The pool and hot tub were beautiful, and while we didn’t use them, they were very clean. It is a very pet friendly place, but doesn’t smell of animals, and there’s no sign of them (unless you meet one in the hallway). The always available hot chocolate and coffee machine was AMAZING! Highly recommend the hot chocolate. We only saw the cleaner once in passing (they don’t go in your room while you’re there), and she was so nice! There’s also extra supplies for you in the main hall closet should you need them (extra towels, tooth brushes, etc.). It truly felt like a home away from home. The only “downside” is that the walls are a bit thin so you can kind of hear what your neighbors are doing if they’re being rowdy, but that’s more managing personal volume levels. 10/10, we’ll definitely stay again!

We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay.

Perfect boutique stay

Our stay here was delightful in every way.

I cannot say enough wonderful things about our stay at The Weston. From the moment we arrived, it was clear this was a truly special place. The property is absolutely beautiful, with a timeless Vermont charm that feels both luxurious and welcoming. Every space is thoughtfully designed, impeccably maintained, and filled with character. What made our stay even more memorable was the incredible hospitality. Every member of the staff was genuinely warm, attentive, and eager to make sure we had everything we needed. The level of service was exceptional and made us feel like valued guests rather than just another reservation. Dinner at the inn was one of the highlights of our trip. The food was outstanding, beautifully prepared, and every bit as memorable as the setting itself. It was the perfect way to end the day and added so much to the experience of staying here. The Weston is one of those rare places that manages to feel elegant, peaceful, and incredibly personal all at once. It is the kind of property you hope to find but rarely do. We left wishing we could have stayed longer, and there is no question that we will return. If you are visiting Vermont, do yourself a favor and stay here. It is truly unforgettable.

The bar tender in the lounge on Saturday 10/18 was not friendly. Seemed like he didn’t like his job. He was the only one working and there were not many customers at the bar. Dining room had no one in it. He just was not attentive to me party of 3 who just wanted to order a drink. Fitness center at the Season was very nice but hours were not very accommodating