Words can't describe how pleased we were with Trailside for our wedding in September 2025, but I'll try. Josh and Ann are incredibly friendly, detail-oriented, and punctual. They answered every email inquiry we had over the 11-ish months of planning our wedding within 1-2 days. And we'd never planned something like this before, so we had a LOT of questions. They made it incredibly easy to plan all the details specific to their venue (every available amenity, dimensions, etc.) without requiring additional onsite visits. They have a default Wedding Weekend plan down to a science, and respected all of our desired deviations from that default plan while still offering specific advice from their years of experience.  The venue itself is lovely. Our guests complimented the quality of the rooms and the beauty of the natural scenery. It's perfectly situated for guests to easily take nature walks, hikes, or ride to the top of Killington peak in their free time.     They provided the services of a Wedding Planner for us as part of their base package, and they 100% delivered beyond our expectations in this regard too. When our primary reception caterer failed to provide services they were contracted for (setting dishware/tableware, washing dishes, filling water glasses), Josh and Anne jumped into action and completely took over. They tableset our entire reception, washed all the dishes themselves, and filled water glasses to ensure dinner could be served as early as possible. When our caterer even forgot one of the primary entrees, Trailside already had a backup plan to order emergency pizzas from nearby and settle the cost at a later date. Even outside the scope of a catering disaster, they consistently helped us to unload and organize our décor, keep the bonfire lit and warm, and kept s'more tables and other amenities stocked. They truly did not have to perform at the level they did, but they even employed additional helpers as needed to make sure we were never behind schedule. It let us truly relax and enjoy the company of our loved ones rather than stressing about logistics.   If you decide to book a wedding at Trailside, please relax knowing the fact that Josh and Anne are looking out for you and will help steer you in the right direction throughout the process- having a very natural schedule, easy room booking process, and picking quality vendors (they only onboarded our failed reception caterer by exception to their standard list and by my wife and I's explicit request - they no longer approve that vendor for weddings at Trailside). If you're deciding between venues, my wife and I would wholeheartedly recommend you pick Trailside and sleep easy knowing your wedding will go smoothly and beautifully. read more

Lovely inn at Killington, 10 minute drive to the mountain. Very clean and simple inn, high quality bedding and linens. Great continental breakfast w local jam and good coffee. Really nice great room in which to relax in front of a roaring fire after skiing or reading a book. Lots of couples and families w kids. Very reasonably priced as well! read more

Adorable warm cozy room. Gorgeous fireplace/great room. Great location. Fabulous advice and tips. So helpful. Loved our stay!!! read more

The Trailside Inn - Hotels Near Me - Killington, Vermont

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The Trailside Inn is a lovely venue, and I don't often use the word "lovely". It's in a great location, run by super nice people, and has so many positives. Any possible negatives have been well documented in other reviews (walls are thin, yes; no TVs in room, so what.) If you are looking for a wedding venue this place must be amazing in the summer, but for us it was a perfect ski chalet complete with boot warmers, great breakfast, super comfy bed, and so much more. I am incredulous that anyone could leave less than a perfect review, especially since the innkeepers literally work 12 hours each a day, every day. I will definitely return and would even consider going back in the summer, just to experience it in a different season. Thank you Joshua and Ann for a great stay. read more

The Setting was nice, but the owners were not. The grounds were beautiful and peaceful.

Had reservations there for New Years this year and called them 5 days in advance to tell them that we were sick and tested positive for covid and asked them what they could do... they said many folks called to cancel as they too were sick with covid and that there was nothing they could do! So they took $750 of our money to stay there for 3 nights and wouldn't even offer a voucher. We stayed last year bringing several friends to also book rooms there as it's close to the Mountain. So they cashed in on all of us sick with covid, not a nice thing to do during a pandemic. I guess the money is more important than repeat customers and building positive relationships! We and our friends will not return to this establishment. I think it's a shame to not offer anything back and take advantage of good people who have supported their small business. They called us and left a message coaxing us to cancel, they also sent an email saying we could get $65 tax back if we canceled, I'm convinced they just wanted to re-rent our room out so we purposely did not cancel. They should feel ashamed for making all that money off of sick supportive customers. Vernon, CT read more

What a perfect place to stay for a Killington trip! Josh and Ann are excellent hosts with friendly conversation and advice about the area for all. It's like staying at a home away from home. Rooms are cozy and beds are comfortable. The common area is great for breakfast or a game of scrabble by the fire. I highly recommend for anyone visiting the Killington area. We can't wait to come back soon! read more

The Trailside Inn - Hotels Near Me - Killington, Vermont

Great place for a ski weekend! Complementary breakfast, boot driers for your ski boots, and a cozy fire to return to! Plus a game room to keep you and your kids entertained. Rooms were clean and the owners couldn't be nicer read more

Total disappointment. Lack of cleanliness and respect for being costly... I will never go back. Leak in ceiling and they gave us 2 hand towels. They are not happy people. So expensive - not worth it!! read more

We had our wedding here in July 2022. If you are in doubt at all, book now! You will not regret it! Ann and Josh are incredible hosts and absolute wizards at helping you organize vendors and plan wedding details. The site is beautiful and all our guests are still raving about how much fun they had over the wedding weekend. The game room was a big hit and Josh and Ann helped us with all our personalized touches, like photos over the fireplace and homemade décor for the ceremony. The Trailside Inn was the perfect spot for our dream wedding and we could not have asked for a better weekend! read more

Wow! What a place to have a wedding weekend! Having grown up in Vermont I've been to a lot of "quintessential Vermont weddings" but the Trailside Inn has stepped it up a notch. Our friends had a casual welcoming party Friday evening with wood fired pizza and fresh Long Trail on draft. Yards games included corn hole and frisbee along with a fire pit and s'mores. Saturday's wedding and rehearsal were also hosted on site and couldn't have been better. The wedding tent was decorated beautifully and the food was prepared by the same people who run The Backroom in Pittsfield, Vermont a small restaurant that's hard to make a reservation at in the winter. From the small bites served at happy hour to the main course everything was spectacular. The band was so good nearly every table emptied and danced the rest of the night away before the after party moved downstairs to the adult game room (beer pong, foosball, connect 4, giant jenga, corn hole, etc.) The location of The Trailside Inn couldn't be more centrally located for adventurous wedding parties with mountain biking, road biking, hiking, golfing, river tubing, paddle boarding, and kayaking all available within a 2 - 20 minute drive. If you're planning an intimate wedding or group event for 100 people or less this place is perfect! The Innkeepers Josh and Ann are attentive and seemed to have everything under control from start to finish, even with on and off again passing sun showers the day of the wedding. read more

A truly wonderful place!! Quintessential Vermont Inn, complete with friendly, affable & cool innkeepers (Joshua & Ann ). Ann made a point to call me directly, to let me in on a discount they were offering as I was riding a Fondo up there ... saved me $20 We will be back during Ski Season!!! read more

Just spent the weekend here, this was our second time coming to the Trailside and once again we loved it. Three people in a bunk room, simple, clean, what we needed for a great price. Met with Josh (one of the owners), very cool guy, helped in everyway possible, everyone is encouraged to get out of your room and hang out in the middle of the hotel in a social room. Bring some beers or wine or whatever makes you happy. Very chill place off of the access road, less traffic, less people, has a very homey feel to it. Simple rooms, clean bathrooms, fireplace is massive, cool social room byob concept Shuttle will pick you up and take you home for free. Delivery from iPie is very convenient. I'll be coming back again for sure read more

My husband and I drove up to Killington for the night on a whim and lucked out to get the last room here as a walk in! We were even thrown a last minute discount off the room price. The owners are so nice and quick to give recommendations for food and daytime activities. We were looking for a place off the beaten path for a night to ourselves and this was the perfect setting! I was a little surprised at no TV in the room, but it actually didn't bother us. The night we stayed the majority of the inn was rented for a wedding. Not only did the owner move some things around so we would have a quieter experience (without us even asking) but we never felt like we were intruding on someone else's "turf" read more

Amazing place to stay! So clean and super nice area to eat and hangout. Owners are very kind and take great care of there guests. Highly suggest staying here!!! read more

Watch out for hidden fees! The hotel itself was super cute and brand new. Lobby is cozy with a nice big fire place and the rooms still smell new. My boyfriend and I tried to cancel Friday night at least 48 hours in advance because we could not make it up until Saturday and they would not let us cancel (even though that is plenty of notice for most hotels).. So we paid for 2 nights when we only stayed for one. Then on top of that they charged us extra fees for "clean towels and sheets". I feel like that is a basic service that should be included in a price of a hotel? if we didn't pay the extra fee, would we have dirty towels? To top if off we paid this extra service charge for the night we didn't even stay there. Not to mention the hotel did not have heat or much hot water - maybe due to the storm? (Also no TVs) Can't blame them for this - but shocked that they are charging all of these extra fees when they don't even provide the basics. They quoted us $125.00 per night (which we only stayed 1 night) and were charged about $326.00. I would have stayed at this hotel again in a heartbeat. People were friendly and super clean. But feel like was taken advantage of big time. Stay elsewhere! read more

My wife and I stay here for business. You won't find a more cozy, clean and friendly place anywhere! Not like a hotel or bed and breakfast, but falls somewhere in between. Huge lobby fireplace, large HDTV, comfy cushioned chairs and "Harry Potter" like tables for eating a Vermont snack. Rooms are spacious, tidy and modern. Caretakers Shelia and Tim always make our stay special! LOVE this place! read more

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. read more

We spent the weekend here over MLK weekend and could not have been happier. Ann was super nice and accommodating on our late night arrival, the rooms where simple and clean, and the main seating area was inviting. It was also nice to be away from the crowd on such a busy weekend. Definitely worth a stay! read more

Had a great experience here on a family vacation, very cozy feel and the innkeepers were very friendly & accommodating.

I just went to a wedding at The Trailside Inn and wanted to review it here because it was AMAZING and anyone who wants to get married in Vermont or New England should know about this place... First of all, the setting is absolutely idyllic. The area for the ceremony was set in the woods by the cutest little babbling brook, there was a great backyard/deck area for the rehearsal dinner/BBQ, bonfire ring for roasting marshmallows, tent for the reception, and the first floor of the inn has this beautiful great room where everyone can hang out throughout the weekend. Second, the innkeepers (Josh and Ann) were beyond wonderful - they were so involved with every aspect of the planning, so helpful throughout the set-up, available for every question and request - just gems to work with. Finally, it was just so nice to have everyone together in one space for the weekend - especially when people are traveling from so far away to attend a wedding. There was a real sense of family and closeness, and I think a large part of that was sharing the space for the weekend - as well as everyone just being so excited for the wedding. If I could give them ten stars I would!! read more

Super cute and very "Vermont". Great location, clean, friendly and just perfect! Great for a Vermont stay!

Cannot say enough good things about this place, it's beautiful, cozy and run by a wonderful family who make you feel right at home. We cannot wait to return, thank you for all of the hospitality and cool story sharing Ann and Josh!!!! read more

Great place! Comfortable, clean and super accommodating. The owners Josh and Ann are great people and provided us with some awesome recommendations for swimming holes, hikes and places to eat. We felt right at home, cant wait to bring the kiddos next time! read more

This was our first time staying at the Trailside Inn. Considering we stayed on President's weekend, it was very fairly priced at $120 a night. The inn has a modern, but cozy feel. It's clean and simple, which is nice. The owners, a husband and wife team, were super friendly and welcoming. They would chat with the guests and gave us some good recommendations on places to eat. Our room was very clean as well. Nothing too fancy (no TV, which is ok with us, although there is a nice sized flat screen in the common area.) Private bathroom with separate room for shower, which we also liked. The room had a space heater for extra coziness as well as additional blankets and pillows. Our bed wasn't the most comfy, but that might just be personal opinion. We found a nice surprise in the basement...a game room with a pool table, foose ball, board games and a hang out area. My husband and I had fun playing some pool when we first arrived :) Great place for kids to hang out as well. They do offer a continental breakfast with granola, pastries, fresh fruit, coffee/tea and bagels/english muffins. Not a full blown meal, but it was enough for us to start our morning. The husband was usually the one to set everything up and he was always very nice to talk to while sitting at the big wooden tables and benches. If you are looking for a fancy, 5 star hotel with room service, this isn't it. BUT, for a few nights on a weekend visit or even a ski trip (group or family), I think it's a good option. Very affordable and cozy, with great owners which is something we look for. We would definitely stay there again! read more

We stayed for 3 nights in February and had an amazing time. The Inn is incredible, rustic but upscale. The room was very comfortable and very convenient to Killington and the nightlife. The owners are truly passionate about the place and it comes through in their interactions with the guests and the atmosphere that is created. The common room is an amazing gathering place where people from different families, places and even countries meet, interact and forge friendships. We will definitely be back. read more

Josh and Ann are fantastic hosts!! This place is located just a few short miles from the slopes, you are literally a 5-10 minute drive. But it's far enough that you aren't bombarded with the traffic of the access road when you want to leave. The rooms are cozy and homy feeling, and provide all you really need for most short trips up in the ski season. The prices are unbeatable compared to so many things closer and even farther from the mountain. I've honestly paid more for horrible places that don't even compare. The breakfast in the AM is great and uses amazing local supplied stuff where possible. The jam/peanut butter were amazing! The central area is a great idea and invokes the social aspect of coming up and meeting new people while you hang out, so even if you aren't a big group, you can mingle with the larger groups! And the glue that keeps it all together, Josh and Ann are great people. They're happy to help out any way they can, help accommodate any needs you have (within reason - I mean they can't port around TV's and refrigerators to rooms on demand!), and happy to share advice from places to go, to food to eat, to other alternative options in the area besides skiing. Having short little conversations with Josh about random things is some of the best part and best laughs while we stay. If you're looking for a great place to stay, with minimal fuss and great access, this is the place and these are the people!!! read more

This is our second season spending a weekend at the Trailside Inn and we couldn't be more pleased with our experiences! All of the details provided on their website and other spots on the internet make very clear what Trailside is and isn't. It's not the 5 star luxury resort located ski on/off from the mountain with room services and white glove treatment. But they don't pretend to be - and the price point is reflective of that! It is the perfect spot for a getaway up north that provides clean, warm and friendly hosts to help make your time there feel like visiting family. The rooms are good sizes with clean linens and the common areas are wonderfully appointed. Breakfast is continental and delicious with lots of focus on what's local (I'm not an oatmeal eater but their homemade oats mixed with some local natural pb was the perfect start for ski mornings). Josh and Ann couldn't have been nicer - whether just in conversation or in helping find the right apres ski spot after a day on the hill. You can tell they love what they do and bring themselves into making sure people have a wonderful time with them. All in all, for the price, what you get and location to the mountain (5 minutes from the Killington Access Road), it's unbeatable! read more

Clean and cozy. Owners are super nice and helpful. Compared to other places I've stayed on skii trips it's super good!!

The trailside inn is a wonderful place to stay. We just spent this past weekend there staying for the second time in two years. This place will surely become are go to place when skiing killington. The owners are friendly and pleasant to speak with and aim to please there guests. The rooms are perfect. It was hard to find a room that had 3 beds at such a reasonable price. The beds were comfortable and clean. The main room provides the perfect place to sit, relax and talk after a day on the hill in front of a nice fire. Breakfast provided in the morning is perfect for getting ready for a big day on the hill. Hot coffee, home made oatmeal that was hands down the best I've had, cereal, fruit, bagels, dounuts and hard boiled eggs. The natural peanut butter and home made jelly was perfect for toping the bagels. We will be back!!! read more