1. Motel In The Meadow

    1. Motel In The Meadow

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    Chester, VT

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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

    3.5(122 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

    Woodstock Inn & Resort

    Woodstock Inn & Resort

    4.0(235 reviews)
    24.9 mi
    $$$

    Our quaint cottage room was spacious and lovely furnished with antiques. Bedding so soft and…read morecomfortable. Adding to this was the beautiful view of the clear water river behind our room with multiple fire pits with fire wood for our pleasure. We enjoyed sitting around the pit in the evening listening to tge water babbling pass and geese flying in and landing in the river. We would definitely come here again. Also short 2 blocks from shopping and restaurants downtown Woodstock.

    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

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

    Okemo Mountain Resort

    3.3(213 reviews)
    10.2 mi

    I came here to ski on a Thursday morning. I was able to easily park in the main parking lot and…read morewalk to the lodge which was within a reasonable distance. Parking was free. From the main lodge are a couple of very short and slow lifts that take you up to areas which give you access to additional lifts. I really liked the variety of runs and that it wasn't overcrowded. I would love to try some of the other sections of the mountain in the future. The terrain park looks fun (if you're into that). My only complaint was how slow most of the lifts are... but that didn't detract much from my overall experience.

    I have skied Okemo Mountain Resort several times during my road trips to Vermont. Okemo is part of…read morethe Epic Pass resorts owned by Vail which means that if you buy a pass early you can get skiing a reasonable rate, in 2026 the multiday pass was about $75 a day. Getting to the resort is easy, it is located just off the main street of Ludlow, Vt., which was about a 30 minute drive from where we were staying in Londonderry, Vt. There are a number of parking lots; both days we arrived early so we had a choice of the 2 free lots near the base area. Equipment drop off is easy and the walk from the lots is not too far. The biggest issue is to get through the resort to the base lodge entails quite a lot of stairs. The lodge itself is what you would expect, nothing fancy but more than serviceable. The restrooms and changing areas are downstairs, which is made a bit harder by the angled staircase, which can be a bit challenging when you are in ski boots. The changing areas have seasonal lockers, rental lockers and free racks for bag storage which is appreciated. At the base lodge you have 2 lifts that take you up the beginner area and allows you to access the rest of the mountain. The main lift for the main face is a high speed 6 pack with ubble covers for the chairs. From the top you can make it to the other areas of the mountain. We skied all of the areas of the resort the Main Face, the South Face, Solitude and Jackson Gore. Okemo is great for cruising the Blues and groomed Black runs. Even though the conditions were icy and not everything was open Okemo provides plenty of variety and skiing. I really enjoy skiing at Okemo, the mountain is pretty easy to navigate. There are a wide variety of runs especially for intermediate skiers. A really fun and enjoyable couple of days skiing.

    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 July 2026

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