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    Motel In The Meadow

    4.6 (5 reviews)
    Open Open 24 hours

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    Chesterfield Inn

    Chesterfield Inn

    4.7(55 reviews)
    26.3 mi
    $$$

    Relaxing restaurant setting. Tables are nicely spaced so you can have a table discussion without…read morebothering tables around you. Staff is very pleasant. Always looking after you without overdoing it. Menu is seasonal particularly the produce. The protein offerings only change about twice a year. My wife had the rack of lamb and I had the duck. Both were very good. We have been there several times and have never felt rushed at all. Judy and her team do a great job.

    Always love our stays - and leave looking forward to our next trip!!!!…read more Staying at the Chesterfield Inn Bed and Breakfast is never a disappointment. From the moment you walk in you are treated with warm hospitality by the owners Judy & Phil along with their staff. Something that stands out is the staff have been the same, which speaks for the owners. I can't say enough about how friendly, accommodating, and welcoming, everyone. We stayed in the main building, in rooms 17, 15, 12 & 14 all have cozy accommodations that are spacious and very clean. Room 15 was a two-room suite with a gas fireplace that we enjoyed in the evening. Room 14 also has a gas fireplaced that we enjoyed. Our favorite room is 12 on the first floor with a private balcony. All the rooms have very comfortable beds, and each room has a small refrigerator. Each of these rooms all had a view of the mountains in the background. Breakfast is included and is served in the lovely dining room. Thersa is very friendly and always ensures we have everything. Breakfast starts with fresh baked muffins and fruit. There is always a selection for breakfast from eggs, omelets and either French toast, waffles or pancakes. I have enjoyed different omelets, the Cinnamon French toast, waffles w/strawberries and blueberry pancakes served with warm maple syrup that comes from a local farm. In the afternoon you can relax by the fireplace in the parlor and enjoy a cup of coffee or tea with a variety of fresh baked cookies that are set up for your enjoyment. I highly recommend having dinner in the dining room that is right on the premises at least one night during your stay. The chef prepares great meals, and the menu has a very nice selection. Service has always been exceptional. There is a nice selection of wine, beer and specialty cocktails to choose from. I would highly recommend taking a ride to the "Vermont Country Store" during your stay. The store brought us back to our childhood with the nostalgic toys, rows of penny candy and the original tins of "Charlie chips and much more! Judy and Phil, along with all their staff, are very kind and caring. Thank you all very much for a lovely stay. See you on our next stay. Kathy & Ray Milford, CT

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    Chesterfield Inn
    Chesterfield Inn
    Chesterfield Inn

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    The Upper Pass Lodge - Room with a jacuzzi tub

    The Upper Pass Lodge

    4.6(44 reviews)
    8.8 mi
    $$

    I stayed at Upper Pass Lodge with my son for 5 days while he attended the Chris Lewit Tennis Camp,…read moreand within 24 hours it felt less like a hotel and more like our home away from home. Vince, the owner, genuinely cares about every guest's experience. His pride in the lodge is evident, and I especially appreciated his honesty--he'll be the first to tell you this isn't a luxury four-star hotel. Instead, it's something even more memorable: a comfortable, safe, welcoming lodge full of character. It's like your favorite well-worn pair of slippers or a cozy blanket--relaxed, familiar, and exactly where you want to unwind after a busy day. Dennis runs the bar like Cheers--before long, everyone knows your name. The atmosphere is warm and friendly, and it's easy to strike up conversations with both locals and fellow travelers. The rooms are basic but clean, the beds are comfortable, the water pressure is fantastic, and fresh towels are provided every day (thank you Terri!). We also loved the restaurant and bar, especially the daily specials like Meatball Monday, Taco Tuesday, and Burger Wednesday. The food was consistently delicious and reasonably priced.

    For the 2nd time in a couple of years I stayed at the Upper Pass Lodge as part of a ski trip…read more Located at the base of Magic Mountain in Londonderry, Vt. it is conveniently about halfway between Okemo and Mount Snow where we had planned to ski on the Epic Pass. Upper Pass is a very nice ski lodge with a nice Vermont feel. The room was spacious and clean and in addition to the main bedroom there was a smaller bedroom with bunk beds and a sink. The decor was nice without being overbearing. Plenty of room, good TV, a desk and couple of comfortable beds. The bathroom was fine with a good shower. There was a small coffee maker in the room and they also stocked the room with some breakfast bars. The rooms do not have a refrigerator or microwave. In the lobby of the lodge is the Red Slate restaurant and bar which are not open on Monday or Tuesday. There is also a nice living room with a fireplace, couches and lots of games. Upper Pass Lodge is an excellent option if you are looking to stay in the Londonderry area. The lodge is welcoming and friendly, it has a great feel as an independent hotel, plus on the times I have stayed it has offered outstanding value for lodging on a Vermont ski trip. Okemo is about 1/2 hour away and Mount Snow is a bit further. The Upper Pass Lodge does hospitality right.

    Photos
    The Upper Pass Lodge - Dining room

    Dining room

    The Upper Pass Lodge - Steak Montreal

    Steak Montreal

    The Upper Pass Lodge - In the lounge

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    In the lounge

    Castle Hill Resort and Spa - Pool

    Castle Hill Resort and Spa

    3.4(123 reviews)
    7.9 mi
    $$$

    Stayed here recently for one night and I have to call out the high points. The grounds of the…read more"Castle" building are spectacular. It's so pretty and the landscaping and flowers are wonderful. We loved the pool and hot tub as well. It's very peaceful and relaxing. The Castle building really is gorgeous as well. The staff at the hotel are very nice and want to be helpful. We used the spa and it was okay. The gym is large and well equipped. I had a massage which was okay. The room I was in had a window which faced the road and the traffic noise was louder than the spa music that was playing so didn't lend itself to relaxing. The massage was over $200 so I didn't think it was a great value because I didn't really feel fully relaxed after it. Ask for a treatment room on the pool side of the building if possible. We ate at the restaurant and it was pretty good. Prices were high but seemed to be about on par with another meal we had in the area. Service was nice. Our room was okay...very spacious but the lack of outlets is tough to manage in 2025 with so many devices to charge. I understand the building is very old so I get that there aren't a lot of plugs. My Verizon connectivity was terrible in the whole area and due to a wide-scale outage, Wifi was not working when I was there, which was problematic because I had to take a business call. That and a couple of other issues with our room led to us leaving early to find someplace that had a working Wifi connection but I have to say the staff were helpful and understanding. It was the off season and I think maybe they were a little short staffed but I get that it's tough for businesses these days. Overall, this place was fine and it is very beautiful.

    We booked a weekend getaway at Castle Inn Spa in Vermont after seeing the photos online, and I was…read moreso excited to stay here. The setting is beautiful, and the property has a lot of history -- over 125 years old and once belonging to Governor Fletcher, with only 12 rooms. Unfortunately, our stay was very disappointing. We checked into Room #9 and right away noticed issues. The bathroom door lock was broken, and I ended up getting stuck inside until my husband let me out. There were also many dead bees on the floor when we arrived, and by the next morning we saw live bees in the room. Since the windows didn't open, I had no choice but to kill them. Service was limited -- no housekeeping even when requested, and the hotel felt very understaffed (likely because it was off-season). The spa treatment was okay, but there was only one massage therapist available. The pool area was relaxing, but that was the highlight. The bee problem got so bad that we cut our stay short. Although we had booked for three nights, we left after just a day and a half, checking out at 9 p.m. on the second night because it became unmanageable. Staff sent a technician, but the only solution offered was to spray, and the bees kept coming back. The environment and historic charm are wonderful, but the property isn't being maintained to the level it deserves. Sadly, I don't see myself returning.

    Photos
    Castle Hill Resort and Spa - Room

    Room

    Castle Hill Resort and Spa - Gym

    Gym

    Castle Hill Resort and Spa - Main house

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    Main house

    Okemo Mountain Resort - $$$ but soo... worth it.

    Okemo Mountain Resort

    3.3(215 reviews)
    10.2 mi

    Okemo was my first Vermont ski experience, and it absolutely delivered. I took the Paragon Sports…read morebus up from New York for what I believe was a three-day weekend, skied Saturday and Sunday, maybe squeezed in a half day Monday, and came back that afternoon. It was definitely cold, but we caught beautiful sun and good conditions, so the whole trip felt worth it almost immediately. Jackson Gore was the highlight for me. The day we were there, it was pretty empty, and we were able to lap that area over and over again with no real lift line. There is a particular kind of joy in skiing 10 to 20 uninterrupted laps when the sun is out, the snow is holding up, and nobody is making you fight for space. Compared with the massive resorts out west, Okemo is obviously a different kind of mountain. Still, the terrain volume felt excellent for Vermont, especially because the trails were well kept, accessible, and easy to keep moving through. The whole place felt comfortable without being sleepy, polished without being sterile, and family-friendly without losing the actual fun of skiing. Ludlow and the surrounding area also add a lot to the experience. It has enough Vermont charm and alpine presence to make you feel genuinely away from New York, the tri-state area, or any other Northeast city you might be escaping from for the weekend. I only went once, but I left wanting to come back, bring my kids, and use Okemo as a starting point to explore more of the region.

    My brother and I took a 2 day, 3 night ski trip back in January. We were there during the week and…read moreone day called for iffy weather (turned out to be beautiful) so the slopes weren't crowded. We never had to wait for a lift. The staff was always friendly when we had interactions and the mountain was well maintained. There were plenty of routes to take depending on your skill. I kept to the easier slopes while my brother tackled them ALL.

    Photos
    Okemo Mountain Resort - 3.16.23

    3.16.23

    Okemo Mountain Resort
    Okemo Mountain Resort - 1.27.24

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    1.27.24

    Motel In The Meadow - resorts - Updated September 2026

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