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.

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

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.

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What Guests Say About Our Killington Rentals For Large Groups

Bryan

Boston, MA
West Park Chalet at Killington

Great place perfect for a ski getaway. Close enough to the mountain to make it easy to get there and back, but far enough away to feel private. Place is in excellent condition and an excellent option for a group ski getaway. Would stay again.

Jimmy

Denver, CO
Fun In Fun Out Ski Home — Both

Everything We Needed: Two hot tubs, two saunas, awesome outdoor hangout space. Lots of rooms and bathrooms. Really cool to have the whole house to ourselves, nice and secluded neighborhood. Right in the center of town with stores 1-2 mins away. Cool hiking trails all around. Communication was easy, host was responsive and check in was a breeze. Lots of parking. Would stay here again anytime. Really cool spot.

Cheryl

Saint Marys, OH
Killington Mountain Retreat

We traveled there for a family ski vacation and enjoyed the stay. The house was comfortable. Best hot tub we have had in a rental. Location is great.

Timothy

New York, NY
Tanglewood Vista at Killington

Great house, friendly host, perfect location for our snowboarding trip in Killington/Pico. Highly recommended for large size groups. Lots of beds and three full bathrooms!

More Killington Vacation Rentals

Interior of a vacation-rental house in Killington, VT. A windows shows a view of birch trees in the Vermont winter.

3/4-Bedroom Homes

Living room of a spacious Killington vacation home with luxurious furnishings and large windows.

Luxury Rentals

Winter view from Killington Mountain in Vermont. Ski lifts under a setting sun.

Ski On, Ski Off Condos, Cabins & Houses

Deck of a cabin with a hot tub, surrounded by a beautiful Vermont winter landscape.