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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(54 reviews)
    26.3 mi
    $$$

    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

    This place is fantastic! Gorgeous location and an authentic BNB…read more They have pet friendly rooms, in a separate building, which is great for guests with allergies. The rooms also don't smell like dog, which is impressive, most do over time! The room I stayed in had a cozy fireplace, and they can do room service for dinner or breakfast. Breakfast was amazing too. Everyone here was so kind and helpful, and even sent me an item I misplaced in the room... that made it to me in Maine in 2 days. Amazing!

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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(43 reviews)
    8.8 mi
    $$

    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.

    In Londonderry VT we stayed here for a weekend in March to ski at Magic Mountain. It is walking…read moredistance to the mountain, it is clean, the on site restaurant and bar are awesome, great food, and the staff is very friendly. The downside is it extremely loud, we stayed on the first floor, the people above us, we heard every step, like the floor makes cracking noises. It is dog friendly, nice, but when someone leaves their dog at 8am and it barks incessantly, not cool. An update of the pillows would also be nice.

    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
    $$$

    We arrived here in the late afternoon on a Monday. The property is about 3.5 miles southwest of the…read moretown of Ludlow on Hwy 103. You pull in at a motel that fronts the highway - the sign reads "The Pointe at Castle Hill". Regardless of which property you stay at, you check in there. Afterwards, you proceed up the hill to the inn. You park either just in front of the building or, if the spaces are full, there is a bit more space to the side of another building close by (probably their spa). We never heard any traffic noise during our entire stay. The building itself is about 120 years old, built by a former Vermont governor from this area. It still has the feel of a mansion, with lots of dark wood finishes inside. They have a small desk in the large foyer when you enter who can assist as needed. There is also a lounge with couches and chairs (for reading, mostly). The restaurant is also located on this level. The wide staircase to the upper floors is to the left off the foyer. The 2nd floor had at least 9 rooms. Down the hallway there was another smaller staircase up to the 3rd level, which I think had fewer rooms (I did not go up there). Our room was nice, with a queen sized 4-poster bed (you might enquire if they have a room with a king-sized bed). There was plenty of additional floor space, with a small table and chairs near the front windows. There are a number of relatively subtle upgrade touches like the phone line and water pipes for the adjoining bathrooms. A few things we noted about our room: * It had limited electrical outlets, which was addressed via power strips for each of the main plugs. * There is no central air conditioning, which is probably fine for this latitude (barring some heat wave). You can open the windows for a breeze, as needed. * The heating is central and is not turned on until some point in the season when it turns sufficiently cold. They do offer a space heater in the room (if needed), there is a fireplace (we didn't use ours), and the comforter was quite warm. * The amount of counter and table space available was limited (due to the small antique table). This wasn't a huge issue, but you have to be mindful of where to leave things like a wallet, glasses, phone, etc. You can book a massage at the spa, but we did not make use of that service. The hotel's fine dining restaurant is a great option for a special occasion meal. You should book this in advance (I'm not what is a safe time - at least a month or two, I'd guess). On the night we ate there, we had a formal oval dining room for the home to ourselves for half of our meal, as the larger dining room across the hall was full from a tour bus. The food was very good! They also apparently serve a modest breakfast here in the mornings starting at 8 a.m., but we were trying to get an early start each day and ended up getting breakfast in Ludlow instead. Given the somewhat isolated location, your dining options outside the hotel are a bit limited. There is at least one restaurant in Proctorsville (within 0.5 miles). There are a few restaurants in Ludlow, but many have varying days on which they're closed during weekdays. It may be easier on weekend, and is almost certainly easier in the winter, as there is a ski resort adjacent to the town. Also, Ludlow apparently suffered flooding in July of 2023, so that appeared to have impacted the number of businesses / restaurants that were open downtown (at least temporarily). Another observation about location - on the two full days we had in the area, we drove 45+ minutes to the north both days to check out a variety of places near Windsor and Lebanon. That wasn't a problem, but if I had the same itinerary again, I might have stayed one night at Castle Hill (and dined at their restaurant) and then moved on to lodging closer to other things we were touring. If you are going for a cozy / romantic country inn vibe, this is a great place to stay. There are just some trade offs vs. the location. Overall, we enjoyed our stay here.

    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.

    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

    Woodstock Inn & Resort

    Woodstock Inn & Resort

    4.0(236 reviews)
    24.9 mi
    $$$

    Still one of the nicest resorts in the area. Beautiful well appointed room with a very plush and…read morecomfortable bed. I had a small problem with a barking dog somewhere near me when I first got there, had a nice chat at the front desk about how I was working this weekend and needed to be able to sleep and never heard the dog the rest of the weekend. The restaurants were great but the best part is the old fashioned bell men...especially Kevin!!! Look forward to next time!

    I saw the pictures taken by famous fall blogger Caitlin Covington as well as another lady whose…read morename I can't remember, while doing research for this trip. I also found out it holds 1 Michelin Key, which is their rating system for hotels/lodging parallel to their famous restaurant ratings. We arrived on Monday (Indigenous Peoples Day) so most people were wrapping up their long weekend. While it was still fairly busy, we never felt it impacted our experience. I was even able to work on a job application! The hotel itself is gorgeous, with many spots to capture mesmerizing photos of nature & people. The rooms are more traditional & country house/cottage style which also fits the aesthetic many young women want on a trip to arguably one of the best New England towns. The hotel is its own landmark/tourist destination as you'll constantly see groups lining up at the front to get a glimpse & small photoshoot session of the iconic facade!

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    Woodstock Inn & Resort - Back Den area

    Back Den area

    Woodstock Inn & Resort - Steel cut oats

    Steel cut oats

    Woodstock Inn & Resort - Fitness Pool and Courts

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    Fitness Pool and Courts

    Motel In The Meadow - resorts - Updated July 2026

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