Trailside Village holiday homes

We found 11 holiday rentals — enter your dates for availability

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May 2026

June 2026

Holiday rentals with weekly discounts – Trailside Village

Showing deals for:28 Aug - 4 Sept

3-story Vermont chalet on sloping terrain, with lawn and trees all around beneath a clear blue sky.

Wonderful

(48 reviews)

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

Killington

7% off

for 7 nights, 1 home

NZ$1,128 per night

includes taxes & fees

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

Exceptional

(63 reviews)

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

Killington

7% off

for 7 nights, 1 home

NZ$1,023 per night

includes taxes & fees

Exceptional

(58 reviews)

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

Killington

7% off

for 7 nights, 1 apartment

NZ$446 per night

includes taxes & fees

Exceptional

(31 reviews)

Trailside Village #8: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Killington

7% off

for 7 nights, 1 apartment

NZ$680 per night

includes taxes & fees

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.

Exceptional

(28 reviews)

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

Killington

7% off

for 7 nights, 1 apartment

NZ$708 per night

includes taxes & fees

Exceptional

(73 reviews)

Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.

Killington

7% off

for 7 nights, 1 apartment

NZ$1,200 per night

includes taxes & fees

The living room of this upscale ski-on ski-off Killington condo features a wood-burning stove and a smart TV with premium cable.

Exceptional

(63 reviews)

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Killington

7% off

for 7 nights, 1 apartment

NZ$439 per night

includes taxes & fees

Exceptional

(24 reviews)

Trailside Village #3: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Killington

7% off

for 7 nights, 1 apartment

NZ$485 per night

includes taxes & fees

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.

Exceptional

(25 reviews)

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

Killington

7% off

for 7 nights, 1 apartment

NZ$424 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Trailside Village

Premier Host

Ski-In/Ski-Out Killington Chalet - Hot Tub, Fireplace & Views

Sleeps 8 · 4 bedrooms · 3 bathrooms

Trailside Village #3: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Sleeps 4 · 1 bedroom · 1 bathroom

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Sleeps 4 · 1 bedroom · 1 bathroom

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

Sleeps 4 · 1 bedroom · 1 bathroom

Trailside Village #8: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Sleeps 8 · 3 bedrooms · 2 bathrooms

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

Sleeps 4 · 1 bedroom · 1 bathroom

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Trailside Village holiday homes

Holiday rentals with weekly discounts – Trailside Village

Showing deals for:28 Aug - 4 Sept

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

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

Find spaces that suit your style

Find the best place to stay - Trailside Village

Ski-In/Ski-Out Killington Chalet - Hot Tub, Fireplace & Views

Peace of mind

More quality time

All the privacy of home

More for less