Killington Large‑Group Cabins & Houses

Condo Complexes

Another option for a big group, instead of renting a large house, is to book multiple units at a condo complex, giving you more privacy and independence while you stay close to each other and enjoy access to shared amenities like pools and fitness centers. This setup lets you adjust your guest count as plans evolve, and each traveler can choose a unit that fits their budget and length of stay. Depending on your preferences, this can be a great configuration for your family reunion, group of friends or corporate retreat.

Trailside Village

Trailside Village is an upscale community of condos and houses offering a prime ski-on/ski-off location at Killington. It’s an excellent choice for large groups seeking both togetherness and personal space. The community features multiple condos within the same building, and condos #3/4, #5/6, and #7/8 each share an entryway.

With direct access to the Great Eastern Trail, Trailside Village makes hitting the slopes effortless, whether you’re here for skiing, snowboarding, or summer hiking. Inside, the bright, spacious condos are designed for comfort, with many featuring hot tubs, cozy fireplaces, and cedar saunas—ideal for unwinding after an active day. Most properties are also pet-friendly, so your faithful furry companions can join in the adventure. Plus, Killington’s top dining, shopping, and nightlife are just minutes away, ensuring plenty of après-ski entertainment.

Browse All Our Trailside Village Condos

Drone view of the buildings that make Trailside Village in Killington, next to a road, forests around, mountains nearby, in the Vermont winter.

Step into comfort and adventure with this 3-bedroom ski-in/ski-out retreat, located just steps from the ski trail for seamless access to the slopes (weather permitting).

Trailside Village 6

3 Bedrooms
2 Bathrooms
8 Guests

Starting at $550/night

Trailside Village Condo #5 is a charming 1-bedroom, 1-bathroom slopeside retreat on Killington’s Great Eastern Trail with ski-in/ski-out access.

Trailside Village 5

1 Bedroom
1 Bathroom
4 Guests

Starting at $250/night

Trailside Village Condo #3 is a cozy, pet-friendly, 1-bedroom condo with true ski-in/ski-out access on Killington’s Great Eastern Trail.

Trailside Village 3

1 Bedroom
1 Bathroom
4 Guests

Starting at $250/night

Trailside Village Condo #8 is a spacious 3-bedroom, 2-bathroom slopeside retreat offering ski-in/ski-out access on Killington’s Great Eastern Trail.

Trailside Village 8

3 Bedrooms
2 Bathrooms
8 Guests

Starting at $550/night

More Condo Complexes in Killington, VT

Killington Center Inn & Suites
- Main road of Killington, 1.3 miles from the resort with shuttle bus access. Summer pool.
Topridge Townhomes (ski-in/ski-out)
- Upscale & spacious. Private hot tubs, fireplaces & decks with BBQ grills. Sports Center with indoor/outdoor pool, gym, tennis, sauna and hot tubs.

Mountain Green Resort
- Close to golf course and Snowshed base. Shuttle to mountain. Spa, gym, indoor/outdoor pools, restaurant, ski shop, fire pit & grills.
Glazebrook Townhouses
- Pool & tennis courts in summer. Fireplace & private deck.

The Woods Resort & Spa
- Indoor pool, sauna, hot tub, tennis, spa, fitness center & restaurant.
Trail Creek Condos
- Close to golf & mountain. Hot tubs, pool & clubhouse.
Whiffletree Condos
- Next to golf course. Shuttle to mountain. Ski home. Tennis & pool in summer.