GREAT EASTERN TRAIL
Great Eastern Slopeside Cabin
A nearby ski-in/ski-out log cabin option with four bedrooms, four bathrooms, private hot tub, cedar sauna, and game room.
- BEDS
- 4
- BATHS
- 4
- GUESTS
- 8
TRAILSIDE VILLAGE KILLINGTON, VT
Destination slopeside: ski-in/ski-out Vermont vacation rentals on the Great Eastern Trail.
SKI IN • SKI OUT LIVING ON THE GREAT EASTERN TRAIL
SLOPESIDE ACCOMMODATIONS
Impeccable Personal Service and Meticulous Attention to Detail. Every Time.
Trailside Village offers an exclusive collection of 7 luxury condominiums and 2 featured homes, each providing unparalleled ski-in/ski-out access to Killington Resort's world-renowned slopes.
Professionally managed by Simple Vacation Rentals, every property features private hot tubs, stunning mountain views, and the finest amenities for an unforgettable Vermont escape.
AT A GLANCE
TRAILSIDE VILLAGE IN KILLINGTON, VT
Trailside Village is a ski-in/ski-out vacation rental community in Killington, Vermont, with condos and homes positioned on Killington Resort's Great Eastern Trail. Guests choose Trailside Village for direct slope access, private hot tubs, mountain views, pet-friendly stays, and professional local management.
- Location
- Trailside Village in Killington, Vermont, on Killington Resort's Great Eastern Trail.
- Rental Types
- 7 luxury condominiums plus 2 featured homes, including one-bedroom and three-bedroom condo options.
- Slope Access
- Direct ski-in/ski-out access for winter stays at Killington Resort.
- Amenities
- Private hot tubs, mountain views, fireplaces, BBQ grills, modern kitchens, and pet-friendly options.
- Managed By
- Simple Vacation Rentals, with booking support through Ski On Ski Off.
- Best For
- Families, couples, groups, and guests who want slope access without driving to the resort.
FEATURED HOMES
Distinctive properties for discerning guests
FEATURED
The Navillus
4 BEDROOMS
Ski In/Ski Out • Private Hot Tub • Mountain Views • Pet Friendly
FEATURED
The Matterhorn
4 BEDROOMS
Ski In/Ski Out • Private Hot Tub • Mountain Views • Pet Friendly
SLOPESIDE CONDOMINIUMS
Refined comfort in the heart of the mountains
One-Bedroom Condos (4 available)
1 BEDROOM
Ski In/Ski Out • Private Hot Tub • Mountain Views • Pet Friendly
Three-Bedroom Condos (3 available)
3 BEDROOMS
Ski In/Ski Out • Private Hot Tub • Mountain Views • Pet Friendly
FRIENDS OF TRAILSIDE VILLAGE
Nearby Ski On Ski Off options when your group needs a different fit
HIGH RIDGE SKI TRAIL
The Mountainside House
A large slopeside Killington house for bigger groups, with five bedrooms, six and a half bathrooms, mountain views, and private shuttle-out service.
- BEDS
- 5
- BATHS
- 6.5
- GUESTS
- 16
SUNRISE SKI VILLAGE
Vistas Home at Sunrise
A nearby four-bedroom mountain home with ensuite bedrooms, private hot tub, grill, Sunrise amenities, and ski access when conditions allow.
- BEDS
- 4
- BATHS
- 4.5
- GUESTS
- 8
PREMIUM AMENITIES
Every detail considered
Ski In/Ski Out Access
Direct trail access to Great Eastern
Private Hot Tubs
Every property features a private hot tub
Premium Amenities
BBQ grills, fireplaces, modern kitchens
Pet Friendly
Your furry friends are welcome
Mountain Views
Spectacular Vermont landscapes
KILLINGTON RESORT
Vermont's premier ski destination
Trailside Village is ideally positioned on the Great Eastern Trail at Killington Resort, offering genuine ski-in/ski-out convenience to 155 trails across 1,509 acres of exceptional terrain.
Experience the perfect blend of adventure and luxury, with immediate slope access and the comfort of your private mountain retreat just steps away.
QUICK ANSWERS
Helpful details for planning a Trailside Village stay
UPDATED AUGUST 30, 2026
Is Trailside Village truly ski-in/ski-out?
Yes. Trailside Village offers direct ski-in/ski-out access to Killington Resort's Great Eastern Trail, so guests can reach the slopes from the property area.
Do all Trailside Village properties have hot tubs?
Yes. Every Trailside Village rental featured here includes a private hot tub for apres-ski relaxation.
Are pets allowed at Trailside Village?
Yes. Trailside Village rentals are pet friendly, so guests can bring their dogs on a Killington vacation.
How many rentals are available at Trailside Village?
Trailside Village includes 7 luxury condominiums, with one-bedroom and three-bedroom options, plus 2 featured ski-in/ski-out homes.
Who manages Trailside Village rentals?
Trailside Village rentals are professionally managed by Simple Vacation Rentals with booking support through Ski On Ski Off.
PLAN YOUR STAY
Begin your mountain escape
