House vacation rentals in Cavendish

The Looking Glass, a modernistic escape

Welcome to The Looking Glass, a modernistic escape located in Barnard, Vermont! With floor to ceiling, south facing windows, you’ll be relaxing in comfort while taking in breathtaking views of the Green Mountains! You’ll love our commercial grade kitchen, boasting high-end cookware, a Wolf range and Subzero fridge. Take the spiral staircase upstairs to enjoy a long bath before calling it a night in the spacious king bed. Explore Silver Lake & Woodstock! Hike, bike or ski the neighboring trails

Newly renovated. Minutes to Slopes & Trails

Healdville Hideaway has 3 acres of rural charm located on the backside of Okemo Mountain. Charm is a plenty in this 1500 SF single story, newly renovated home with views of the mountain & fields full of wildlife. This modern country decorated home provides the perfect comfortable setting for single or multi family enjoyment. The fully functional kitchen is available for making a quick snack or a full meal. The back acreage is perfect for building a snowman or doing a little cross country skiing.

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets

Wake up in a luxurious bed in a stylish cabin with panoramic Vermont views and a little reading balcony. When ready, step down to the living area to look at faraway hills through oversize doors, a hot cup in your hands. Make breakfast in your Chefs kitchen. Sit/read/talk. Go for a hike. Or a scenic drive to your pick of Woodstock, Simon Pearce, Harpoon Brewery, Okemo, or Twin Farms. Cap it off with a night gazing at stars around the firepit. The Red House is all this and more....

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

The Oaks - secluded rural estate w/ amazing views

Relax in this private house secluded off a 1,000-ft driveway in the hills of NH overlooking Mt. Ascutney and the Connecticut River valley. This is the 45-acre estate known as "The Oaks" previously owned by painter Maxfield Parrish. Huge oak trees and rocky ledges abound. Great for gatherings with family or friends. Close to Dartmouth College, Woodstock, and ski areas - or just sit on the porch and take in the views. Weddings and reunions can be hosted (tent rentals and catering by others).

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Greystone 1830

"Greystone" is a charming stacked granite home built in the 1830's as a tavern and one of 4 original structures that made up Hammondsville VT. Greystone is just miles from Woodstock, and down the road from the Green Mountain Horse Association (GMHA). It's a short drive to Killington or Okemo and many other Vermont destinations. Greystone is just off VT Rt 106 on a large lot with a circular driveway and plenty of room for parking. The home is fully renovated and modernized.

Meadow View. 35 acres outside your door!

Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)