Villa holiday rentals in Rutland

Woodstock/Barnard Chalet 20 min Killington dog ok

Rarely Available estate - Nightly, Weekly or monthly stays available for winter 2024-5. 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. Its a Stunning Estate on 25 acres of lush Vermont. Woodstock is close and one of New England's favorites. 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 24/25 leases.

100 yrs old 2024! Historic Musician's Villa Bolton

This truly intriguing turn-of-the century home transports guests to the inspiring mood & enduring character of the great & gracious. Built by a legendary musician’s family w/focus on elegant entertaining, this 100 yr old home is ready for guests after 3 yrs of restoration. Remaining true to original form, guests find showpiece architectural acoustics in great room, elevated framework throughout w/timeless archways, dramatic stairway w/ornate balustrade, romantic rounded walls, relaxing patios.

Gorgeous Victorian-Style House w/ Hilltop Pool!

Nestled in a serene valley of the Green Mountain National Forest and boasting 5 acres of maple tree-laden land, this Victorian home is the place for an unparalleled retreat. The 6-bedroom, 3.5-bath vacation rental was built in 1856 and boasts a perfect blend of old-fashioned charm and modern luxury. Spend your days relaxing at the river on-site, taking a dip in the pool, or roasting s'mores at the fire pit. During winter, curl up with a book in the library and gaze out over a snowy hillside.

Huge Stunning Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Welcome to Mt Snow Villas!, Your ultimate mountain experience at Mount Snow. This stunning duplex villa offers a harmonious blend of luxury, comfort, and convenience, making it the perfect choice for large groups, family gatherings, or anyone seeking an unforgettable escape to the mountains. With the indulgence of a Jacuzzi, hot tub, and sauna, your stay promises both relaxation and rejuvenation. ASK US ABOUT RENTING ALL 6 VILLAS AND HOSTING UP TO 60 PEOPLE FOR YOUR NEXT PARTY!

Large Updated Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Relax at Mt Snow Villas!! Welcome to our gorgeous mountain villa duplex nestled in the heart of breathtaking West Dover just 1/2 mile from Mount Snow! If you're seeking a peaceful escape from the hustle and bustle of everyday life, this spacious villa offers a perfect blend of warmth, elegance and modern comfort, making it the ideal getaway for couples, families, or groups of friends.

Cozy, Comfy & Sunny renovated Sugarbush condo

You'll love this sunny stand alone condo/villa with it's proximity to Sugarbush Ski Resort. A short walk to access trails to the lifts and ski home! Located adjacent to the mountain, you'll enjoy this renovated and updated two level space. All new fully equipped kitchen, baths, hardwood floors and Rinnai heater. Outdoor ski locker for all your gear.

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!

Villa with Pool + Fitness Center Access

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!