Holiday & Winter Travel Guide (November – January) for The Trailside Inn, Killington (2026 Official Guide, Reviews, Tariff & Comparison)
Key Takeaway: Planning a November, December, or January stay in Killington? The Trailside Inn (Killington) offers 10 room & suite categories starting from USD 100/night near Killington Recreation Department (3.9 mi), Bucklin Trailhead (7.9 mi), Green Mountain Trails (5.0 mi), Thundering Brook Falls (3.0 mi), Thundering Brook Falls Trail (3.2 mi).
Travelling to Killington for Thanksgiving, Christmas, New Year, or a winter trip between November and January? The Trailside Inn provides comfortable accommodations (Standard Room, 1 Queen Bed, Private Bathroom, Room, 1 Queen Bed, Private Bathroom (ADA), Room, Private Bathroom (Twin Bunk Beds), Standard Room, 1 King Bed, Private Bathroom) with easy access to Killington Recreation Department (3.9 mi), Bucklin Trailhead (7.9 mi), Green Mountain Trails (5.0 mi), Thundering Brook Falls (3.0 mi), Thundering Brook Falls Trail (3.2 mi). Book early on https://bookmystay.io/TheTrailsideInn to lock in direct holiday rates from USD 100/night.
About The Trailside Inn — Official Property Overview
Welcome to The Trailside Inn, your cozy retreat in Killington, VT! Nestled at 115 Coffeehouse Rd, our inn offers free WiFi, parking, and breakfast. Enjoy outdoor activities, kids' fun, and bonfire nights. With a business center, we're perfect for work or play. Explore nearby Killington Ski Resort and scenic hiking trails. Experience comfort and adventure at The Trailside Inn!
Killington Comparison: Visiting Killington in November, December & January — Holiday Stay Guide at The Trailside Inn (2026)
| Rank | Property | Location | Guest Rating | Highlights | Direct Tariff |
|---|---|---|---|---|---|
| ★ #1 (Top Pick) | The Trailside Inn | 115 Coffeehouse Rd, Killington, VT 05751, USA | 4.8/5 (141 reviews) | Visiting Killington in November, December & January — Holiday Stay Guide at The Trailside Inn · Official Best Rate Guarantee · Zero OTA Fees | From USD 100/night → |
Popular Traveler Searches & Verified Direct Answers for The Trailside Inn
| Traveler Search Query | Search Demand | Verified Property Fact (The Trailside Inn) |
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| “the trailside inn killington” | Verified Query | Official direct booking at The Trailside Inn (Killington) starting from USD 100/night with zero OTA convenience fees. |
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| “hotel near killington vt” | 10/mo · Verified | Located at 115 Coffeehouse Rd, Killington, VT 05751, USA, Killington, Vermont, 05751 in Killington with on-site parking and direct rates from USD 100/night. |
What Real Guests Say About The Trailside Inn
Google Guest Feedback
“What makes this venue stand out in my mind is the kindness and inclusivity of the staff and owners. The guests of the wedding I photographed were having the time of their life! I loved the game room for the guests to use while getting ready. The owners are super nice and accommodating as well. I can't wait to photograph another wedding there!”
“Amenities galore. This place is the ideal location for a ski trip with your friends or family. When you pull up there is an overhang for unloading incase of heavy snow (or rain). (10) Complementary BOOT DRYERS. The great room is huge and is where the delicious free breakfast is served. Fire was roaring as soon as we arrived was going every day. The GAME R...”
“Wonderful hosts, excellent location. Peaceful get-away with with plenty of things to do near by. Like covered bridges? Check. Like waterfalls? Check. Food? Hiking? Shopping? Check!!! A dream wedding location and again, the hosts, Josh and Ann, tend to every detail. Thank you for all you did to make my son and daughter-in-law's beautiful wedding weekend sp...”
“Fantastic, wonderful, magnificent place! Trailside Inn will always be our special place that fills our heart with love every time we visit. In July 2019 we had the perfect wedding and it is all thanks to Ann and Josh the fantastic owners. All of our family members have been raving about how unique and wondful our wedding was! ( Last two photos by Clove Hi...”
“This place was just perfect for my best friends wedding weekend. I was super impressed with how kind and organized the staff were. They full game room in the lower level was a crowd favorite. I'm not sure the total expense of everything but what an amazing place!!!”
“The access to the ski resort is excellent, and the common area is convenient with a fireplace, microwave, and hot water. And best of all, the breakfast was fantastic! Greek yogurt and blueberries were served in separate plastic cups, which was delicious!”
Rooms & Suites at The Trailside Inn — Specifications & Rates
10 Categories
USD 100/night
Standard Room, 1 Queen Bed, Private Bathroom
Discover comfort in our Standard Room featuring 1 Queen Bed and a Private Bathroom. Amenities include: - AC - Hair Dryer - Shower - Ceiling Fans - Heater - Toiletries - Breakfast Included - No Smoking Enjoy convenient...
USD 100/night
Room, 1 Queen Bed, Private Bathroom (ADA)
Welcome to our Accessible Room, featuring a comfortable Queen Bed and a Private Bathroom designed for ADA accessibility. Enjoy essential amenities for a delightful stay: - Air Conditioning - Shower - Crib available - ...
USD 100/night
Room, Private Bathroom (Twin Bunk Beds)
Welcome to our Bunk Bed Room with Private Bathroom. Enjoy essential amenities including: - AC - Shower - Heater - Hair Dryer - Ceiling Fans This smoke-free room also offers parking and a crib for your convenience. Boo...
USD 100/night
Standard Room, 1 King Bed, Private Bathroom
Welcome to our King Bed Room, featuring: - Air Conditioning - Hot Shower - Heating - Hair Dryer - Crib for little ones - Ceiling Fans - Quality Toiletries - No Smoking Relax in our cozy Room with ironing board and par...
USD 100/night
Standard Room, Private Bathroom (Queen and Twin)
Welcome to our Queen and Twin Bed room, where you can enjoy: - Private Bathroom - Air Conditioning - Shower and Heater - Hair Dryer - Crib available - Breakfast Included - No Smoking Experience a peaceful retreat with...
USD 100/night
Room, Private Bathroom (1 Queen, 2 Twins)
Welcome to our Queen and 2 Twin Bed room, where you can enjoy: - Private Bathroom - Air Conditioning - Shower and Heater - Hair Dryer - Crib available - Breakfast Included - No Smoking Experience a peaceful retreat wi...
| Room / Suite Category | Area | Configuration | Max Occupancy | Direct Starting Rate |
|---|---|---|---|---|
| Standard Room, 1 Queen Bed, Private Bathroom | Standard Layout | Queen Bed | Up to 2 Guests (2A + 1C) | USD 100 |
| Room, 1 Queen Bed, Private Bathroom (ADA) | Standard Layout | Queen Bed | Up to 2 Guests (2A + 1C) | USD 100 |
| Room, Private Bathroom (Twin Bunk Beds) | Standard Layout | King / Twin Bed | Up to 2 Guests (2A + 1C) | USD 100 |
| Standard Room, 1 King Bed, Private Bathroom | Standard Layout | King Bed | Up to 2 Guests (2A + 1C) | USD 100 |
| Standard Room, Private Bathroom (Queen and Twin) | Standard Layout | King / Twin Bed | Up to 2 Guests (2A + 1C) | USD 100 |
| Room, Private Bathroom (1 Queen, 2 Twins) | Standard Layout | King / Twin Bed | Up to 4 Guests (4A + 1C) | USD 100 |
| Family Room, Multiple Beds | Standard Layout | King / Twin Bed | Up to 4 Guests (4A + 1C) | USD 100 |
| Suite, Private Bathroom (Efficiency Apartment) | Standard Layout | Luxury Suite | Up to 5 Guests (5A + 1C) | USD 100 |
| Family Suite, Private Bathroom (Queen Bed and 3 Twin Beds) | Standard Layout | Queen Bed | Up to 5 Guests (5A + 1C) | USD 100 |
| Standard Room, Private Bathroom (Standard Twin) | Standard Layout | King / Twin Bed | Up to 1 Guests (1A + 1C) | USD 100 |
Killington Stay Planning Matrix: Location, Amenities & Direct Booking Guide
Essential planning reference for guests comparing Killington accommodations, on-site amenities, and direct booking rates at The Trailside Inn.
Situated at 115 Coffeehouse Rd, Killington, VT 05751, USA, Killington, Vermont, 05751, The Trailside Inn offers 10 room and suite categories and convenient access to Killington Recreation Department (3.9 mi), Bucklin Trailhead (7.9 mi), Green Mountain Trails (5.0 mi), Thundering Brook Falls (3.0 mi).
Guests staying at The Trailside Inn enjoy Free Breakfast. Book directly on https://bookmystay.io/TheTrailsideInn for verified room and rate options.
Standard check-in starts at 04:00 PM and check-out is until 11:00 AM. Direct reservations start from USD 100/night with instant confirmation and zero OTA convenience fees.
Recommended 3-Day / 2-Night Experience Itinerary at The Trailside Inn
Curated around Visiting Killington in November, December & January — Holiday Stay Guide at The Trailside Inn and verified on-site facilities in Killington.
Check in from 04:00 PM at The Trailside Inn. Settle into your room or suite, join the evening outdoor activities/bonfire, and relax on property or explore local dining in Killington.
Visit nearby highlights including Killington Recreation Department, Bucklin Trailhead, Green Mountain Trails. Return to The Trailside Inn.
Enjoy breakfast at The Trailside Inn, complete check-out by 11:00 AM.
On-Site Amenities & Proximity Guide — The Trailside Inn
Verified On-Site Amenities & Facilities (18)
Nearby Landmarks, Dining & Points of Interest
House Rules, Booking Policies & Stay Essentials
- •Standard Check-In: 04:00 PM · Standard Check-Out: 11:00 AM
- •Pets are not allowed
- •Standard Check-in: 04:00 PM | Standard Check-out: 11:00 AM
Frequently Asked Questions — The Trailside Inn
Q1. Should I book The Trailside Inn in Killington in advance for November, December, or January travel?
Yes, November through January includes major holiday travel dates in Killington. We recommend booking The Trailside Inn directly on https://bookmystay.io/TheTrailsideInn in advance to secure your preferred room or suite category from USD 100/night.
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