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Trailside Village vacation rentals

We found 22 vacation rentals — enter your dates for availability

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July 2025

18

August 2025

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Find the best place to stay - Trailside Village

Showing deals for: Oct 16 - Oct 19

Stunning 3-bedroom, 2-bathroom retreat with ski-in/ski-out access on Killington's Great Eastern Trail. Cozy gas fireplace and stylish dining table, among other luxury comforts.

Trailside Village #4: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Sleeps 8 · 3 bedrooms · 2 bathrooms

All fees included

Living area flooded with natural light.

BruinsDen- Hot Tub, Foosball, Mountain Views

Sleeps 8 · 4 bedrooms · 3+ bathrooms

All fees included

Tastefully decorated living room with ample space. Trailside Village Condo #5 is a charming 1-bedroom slope side retreat on Killington's Great Eastern Trail.

Trailside Village #5: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Sleeps 4 · 1 bedroom · 1 bathroom

All fees included

Trailside Village Condo #1 is perfect for 4 guests. Relax in the spacious living area with a smart TV, high-speed Wi-Fi, and beautiful views of the Vermont landscape.

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Sleeps 4 · 1 bedroom · 1 bathroom

All fees included

Living area

The Matterhorn House: Killington Chalet w/ Hot Tub, Views, Game Room - Ideal Spring to Fall

Sleeps 8 · 4 bedrooms · 3 bathrooms

All fees included

Chef's kitchen and stylish dining area with views to the Killington landscape in this slopeside 4-bedroom home.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

Sleeps 8 · 4 bedrooms · 3 bathrooms

All fees included

Top rated rentals - Trailside Village

Ski on ski off on Great Eastern Trail!!!

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