Villa holiday rentals in Rutland

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Top-rated villa rentals in Rutland

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Private room in Windsor

4.89 out of 5 average rating, 36 reviews

Private Wing of largest Colonial Mansion in US

Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of Colonial Revival Architecture. Filled with elegance & history, Three US Presidents have slept here. Our 17 Rooms/Suites are individually decorated each with private bathroom & free wireless internet. Set on 14 acres with a tiered terrace offering spectacular views & a custom fire pit. Lots to see in area including Saint-Gaudens Nat'l Park, Quechee Falls, Dartmouth College, etc

Superhost

Villa in Bolton

4.56 out of 5 average rating, 16 reviews

Gatehouse Villa at Blue Water Manor w/pool, lake

Welcome to the Gatehouse Villa at Blue Water Manor! Be spoiled w/all the benefits of resort living, while you enjoy the privacy of this unique vacation property. Our 4BR Adirondack-style villa includes 2 decks w/dining, BBQ & a clean, large living space. Bask in the gloriousness of our inviting heated outdoor pool, or enjoy drinks lakeside, splash in the lake and frolic on the playground. Amazing property w/lake views. Enjoy live music & events year round at the Tavern or the Barrel restaurants!

Villa in Woodstock

4.8 out of 5 average rating, 5 reviews

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.

Guest favourite

Villa in Bolton

4.94 out of 5 average rating, 64 reviews

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.

Guest favourite

Villa in Keene

5 out of 5 average rating, 15 reviews

Keene Villa Near Skiing, Swimming & Hiking!

Indulge in the finer things while staying at this chic 4-bedroom, 5-bath New Hampshire villa, overlooking a 36-hole golf course! With accommodations for 8 guests and an outdoor entertainment area, this vacation rental is perfect for your next getaway! Enjoy grilling out on the patio, reading a book in the library, or watching movies on the projector. Then, head out for an afternoon hike at Goose Pond. End the night by the fire pit with your fur pal, watching the sunset and munching on s’mores!

Guest favourite

Villa in Winhall

4.91 out of 5 average rating, 23 reviews

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.

Guest favourite

Villa in Dover

4.88 out of 5 average rating, 16 reviews

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!

Superhost

Villa in Dover

4.82 out of 5 average rating, 17 reviews

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.

Guest favourite

Villa in Warren

5 out of 5 average rating, 26 reviews

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.

Superhost

Villa in Brownsville

4.79 out of 5 average rating, 71 reviews

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!