Villa vacation rentals in Killington

Authentic and Refined Woodstock/Barnard Estate

Rarely Available estate - Nightly, Weekly or monthly stays available for winter 2025-6. Our 5 br family home is 5 min to Woodstock&Barnard, town centers 20 min to the Killington Skyeship, 35 min to Okemo an 5 min to S6. It's a stunning estate on 25 acres of lush Vermont. Woodstock one of New England's favorite small towns. Grill on the rear deck with your private hot tub. Sip wine on the porch with magical views. Make this your getaway. <2 hr to Boston. Inquire about Winter ski leases.

Stonehouse at Stratton

Create cherished memories in this unique, family-friendly haven. Designed for entertainment, enjoy a wet bar, pool table, ping pong, darts, and more. Heated floors and Bluetooth sound systems add luxury. Each bedroom has a private bath. The expansive kitchen accommodates the entire family, and a fireplace invites warmth after skiing or boarding. Revel in privacy on 4 acres, with a 2-car heated garage. Only minutes from Stratton, this home offers comfort and leisure in every detail.

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

This unique house has a style all its own. with floor to ceiling windows and doors throughout There are 3 levels. top floor has 2 bedrooms with full baths and Hot Tub on the balcony middle level entry; plus Great room: with kitchen, dining, living, activity area with a big table, fireplace and 75 inch television bottom level has 2 bedrooma and 2 full baths

Villa with a Fireplace Near the Trails

Dreaming of a cozy villa with a fireplace? You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Villa Near Biking and Hiking Trails

This villa is perfect for your group! Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Vermont Villa Near the Trails

You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Whiffletree base of Killington outdoor pool

Whiffletree C2 has been totally renovated and looks great. Located at the base of Killington close to mountain biking and snow sports.

Whiffletree base of Killington outdoor pool

Whiffletree F6 is on the shuttle bus route with a ski back trail

Base of Killington with Sports center access

Trail Creek 12, Lovely 1 bedroom close to Mountain