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​The best available rate will always be found on our website.

PLEASE NOTE: We are only open for private wedding events through mid-October.  We will have availability for individual stays 10/21 - 10/24.  We will be reopening for the FIS World Cup and ski season on November 26.
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Brynne

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The Trailside Inn is everything you would expect to see in a Vermont Inn. A gathering area that is welcoming, a comfortable and clean room with a great aesthetic. It is however more than the sum of its parts due primarily to the wonderful family that runs the Inn. Upon check-in we were greeted by Josh who had ample suggestions for our time in Vermont. He knew the area well and gave us options which allowed us to make our vacation unique. Hiking, sightseeing, shopping and visiting breweries dominated our time. We really enjoyed however coming back ‘home’ at the end of each day and sharing our stories with the other patrons and Josh and Ann. Sharing coffee in the morning or a beer at the end of a day made it just feel more like visiting friends. We will certainly visit the Trailside again, not because the beds are the softest (they were great) or the showers are the hottest (just the thing for sore muscles) but because to us, it is now home.

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​ Brozi

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Never disappoints! ​This review is based on my experience staying at the trailside inn on multiple occasions from October till as recent as early March. When you stay this many times in such a short time you expect to find something wrong but was unable to. The rooms were always clean and I mean spotless. The community room is great, for reading a book, sitting by the gigantic fireplace or just watching TV, it's very relaxing, Creates a nice social experience with other guests. None of this could be possible if it wasn't for the inn keepers Josh and Ann, they make you feel like friends and family. Give the trailside inn a shot and you won't be disappointed. A hidden gem.

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Susan

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Just something super cool and simply chic about the trailside inn. I saw the pictures online of the clean, slightly funky room units with the thick slab handcrafted wooden headboards and I knew I wanted to stay there. The main living space with the huge stone fireplace and giant wooden tables was all so quintessential ski country yet hip in a new twist kind of way. I fell in love with my small but perfectly cozy room with the vessel sink, hand-painted mirror and colorful bedspread. The mattress was to die for and I requested immediately to know what brand. The Innkeepers were so nice and helpful…thank you Annie. The blood oranges in the morning and farm fresh hardboiled eggs…well great way to amp up before hitting the slopes.

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​I came here on a company outing and it was a great place. It was very clean and well kept. The innkeepers were very pleasant and accommodating. There's also a games room for those that enjoy board games, foosball and pool. It's one of the best places I've stayed in and made for a great first experience in Killington, VT.!

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​We brought around 40 team members onsite to Trailside in July and had a blast over our three days! Josh and Ann were not only welcoming and hospitable, but very patient with our large group! Everyone really felt at home at the inn and had a great time relaxing with yard games, BBQing and evenings in front of the bonfire. Killington as a whole also offered really great group outings (Breweries, trips to the top of the mountain, navigational courses, etc.). We will definitely be returning!​

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​We hosted a family reunion at Trailside for 4 days and 3 nights. Josh and Ann, the innkeepers, could not have been more accommodating and were consistently available throughout. The Great Room, big back deck, and lower level game room provided numerous options for gatherings throughout our stay. The setting is so casual and perfectly consistent with a getaway in the Green Mountains. The provided breakfast has a delicious local flair.

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​My friends and I have been staying here a few years now, and Josh is always extremely helpful when trying to book our group. He's responsive on email and always works to find the best room for our group.

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​Thanks to Josh and Ann, they did everything they could to welcome our group and ensure that our 3 day event event was a success. The Trailside Inn rooms were great, and the meeting facilities and common areas were clean and comfortable. This is a great place to stay and perfect to host large groups, we will definitely be coming back again.

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​​I attended a wedding reception held here recently, and I feel compelled to gush about it! The wooded site adjoining the inn was beautiful, with a stream running in the background, the food was spectacular, and the servers were all very pleasant. It is rare to attend a wedding and have the food be anything but bland or cold or undercooked, but this place did it superbly!

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​We attended a family wedding here. I can't say enough about what Josh and Ann provide. The atmosphere makes you want to relax and the comforts of fires, yard games and comfortable rooms makes it easy to do so! Every vendor they connected us with was wonderful. If we ever come ski at Killington staying here will be a no brainer but the summer is even better. Bring your little ones and let them play in the stream like kids are supposed to do. Bring your older ones and let them sit in the shade and read. Definitely host your wedding and company event here and definitely have your wedding here!!!

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The Trailside Inn was a perfect home-base for our large group's ski trip. The room and common areas were really clean and comfortable, making it easy to feel at home. I'm a big fan of the fireplace, local breakfast, and sledding hill!

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​This was a PERFECT venue for a wedding! The inn is beautiful, located in a gorgeous setting surrounded by forests and mountains. The ceremony was held along a babbling brook - couldn't have asked for a more picturesque spot! In addition to the venue itself, Josh an Ann, the Innkeepers were incredibly accommodating, kind and caring. They went above and beyond to make every detail of the weekend perfect. It was immediately apparent that they care deeply about their guests, and understand how a personalized touch can make an entire wedding experience feel even more special and intimate. Kudos to Josh, Ann and the Trailside Inn! I couldn't recommend a wedding venue more highly.

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​My friends got married on a rainy Sunday and many of us stayed from Friday until Monday. On nice days, we hung out on the beautiful outdoor grounds and at night and during the rain, the indoor spaces were well set-up to have different groups of people all near each other. The food was excellent, the innkeepers were hardworking and made all the logistics go smoothly. I appreciated that there were different kinds of rooms available all at a different price point and all in the same place. I'd definitely recommend this location.

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​Corporate retreat was awesome! ​Thanks to Josh and Ann, they did everything they could to welcome our group and ensure that our 3 day event event was a success. The Trailside Inn rooms were great, and the meeting facilities and common areas were clean and comfortable. This is a great place to stay and perfect to host large groups, we will definitely be coming back again.

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​​We absolutely loved everything about Trailside! Josh and Ann are amazing and so helpful throughout the planning process and the weekend. The location is gorgeous and, even though it POURED on our wedding day and we weren't able to have the ceremony outside, the tent was beautiful and everything was perfect. Our guests were delighted when they realized we really had the whole place to ourselves. We had the flexibility to do different events throughout the weekend and it was so fantastic to see our guests interacting and getting to know each other. Our guests were comfortable at Trailside and had a great time, and Josh and Ann feel like family!

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​​I came with my entire company, and we had the best time. The rooms were clean, the main area was perfect for hanging out, and the basement was a great place to play some pool and let loose. I had such a fun time sitting by the fire, sledding on the golf course, and just hanging out. Thank you for being such wonderful hosts!

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When I say that we had a PERFECT wedding at The Trailside Inn, that is an understatement! My husband and I got married in August and all of our guests continue to talk about how great the entire weekend was. We live in NJ and were able to do the planning remotely and with a few visits. Ann and Josh helped facilitate communication with the vendors and made sure that no detail was missed. All 80 of our out of town guests were able to stay on site which was a huge plus in our book. It made for a relaxing, reunion type weekend where everyone could gather in the Great Room at anytime from breakfast, to breaks after exploring the area with hikes, to ending the night. Our ceremony was held by the stream, cocktail hour on the back deck and lawn, and the reception under the white tent. The hospitality and warm welcome at The Trailside Inn makes it an excellent wedding venue. If we were to do it all over again we wouldn't change a thing!

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​​So spacious, so many rooms, layout of common area, basement, and rooms was perfect for a huge company outing and lots of fun. Pool table, foosball table, etc are great additions for activities. Great for big events!

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​The Trailside in was great. It was perfect for our family reunion! It fit all 55 of us very comfortably and the rooms were great. The bathrooms and the shower were nice and I really loved the rustic wood floors and decor. The great room was perfect for larger gatherings and card tournaments. The yard was great for the kids to play outside and various lawn sports. Having a fire-pit with chairs was also great. 

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Had a ski trip with the entire company, wonderful place to stay! So spacious, so many rooms, layout of common area, basement, and rooms was perfect for a huge company outing and lots of fun. Pool table, and foosball table are great additions for activities. Great for big events!

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Great weekend, got even greater with inn keeper's local knowledge! My son and I came up for two days of skiing and had a very cozy stay at the Trailside Inn. Josh who runs the place gave invaluable advice to make the most of the time there. He was a great host that took time and connected with you as a guest and really helped making it a wonderful weekend. Definitely recommend others to go there and we want to come back soon again.

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We had a great family room (201) and the location is stunning (much nicer than being on the main strip in Killington for me). It's a great crowd here, everyone sat around the open fire on an evening talking about the day on the slopes and there's a huge games room too which kept our boys happy! The owners, Josh and Ann, are ultimately what makes this place so good - friendly and helpful - they make you feel like you are just staying in a big lodge you've all rented together as friends. Our first, but not our last, visit! Thank you Josh and Ann.

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Fantastic lodging, wonderful people and beautiful location! You absolutely can not go wrong staying at the Trailside Inn in Killington, VT. Josh and Ann are super friendly, accommodating, and available owners. The rooms are adorable and the continental breakfast was the tastiest I've had. Looking forward to going back!

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Quaint, authentic cozy and relaxing! Was only in town for the weekend to compete in the Spartan Beast race being held nearby. Due to waiting too long to book a hotel, I was only able to find a bunk room available for my wife and I. She was very concerned that it would be like being back in a college dorm, but honestly, we enjoyed it and slept like babies on the deceptively comfortable beds. The inn is clean, and rustically cool. The innkeeper, Josh was incredibly friendly and very helpful. We had a very short trip and small window to explore and experience a little slice of Vermont. We followed every one of his recommendations, even the roads to travel to get to our destinations - and they did not disappoint! Our first trip to Vermont and it was incredible. Thanks, Josh and the Trailside inn staff!! A wonderful lasting first impression for sure!!!

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Great local experience! Josh and Ann run their business as a family and it truly makes a great experience. More than just hosts, they engage and get to know their guests at a personal level, enabling them to tailor a unique Vermont experience to all interest and age levels. Perfect for a family vacation, they will get you to all the local spot (lots of map reading) and suggest activities based on what they learn about you. They've also built all the local connections to quickly get you expert resources on whatever interests you may want to pursue. I was part of a large 54 person family reunion and was able to have the space and freedom to experience the best of Central Vermont while also sharing some great extended family time at the property. Especially great was the fire pit, expansive outdoor deck for supervising kid activities and main hall for accommodating dozens of people at a time. Was hard to say goodbye to Josh, Ann and Vermont. We definitely recommend Trailside Inn!

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