Holiday rentals in West Windsor

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

Private, Large 4BR home | Pet friendly | 10 Acres

Okemo & Killington Ski House Large 4 bedroom 2.5 bath, 3,000+ sq ft home located close to Okemo Ski Resort and surrounded by 10 acres of land at the end of a private road! This recently renovated home features 3 levels, a large game room, 5 separate sleeping areas and a large covered porch! Enjoy ultimate privacy with proximity to multiple outdoor adventures including skiing, golfing, hiking and mountain biking. Just a short drive to downtown Ludlow and other surrounding stores in Cavendish.

Chuck's Place

Summer is in full gear! Chuck's is a neat and tidy stand alone home warmly dedicated to your vacation pleasure. Fully stocked! Private and convenient on 7 sunny acres overlooking Mt Ascutney. It's great for folks coming in for hiking, biking-- or absolute relaxation. Brownsville Butcher and Pantry supports many endurance and music events in the village at the base of Mt Ascutney. It's a special gathering place to enjoy wine, beer, ice cream --and the best meat and fish anywhere. We promise.

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.

Cozy Mountain Cabin w/ Hot Tub & Incredible View

Plan your autumn escape to this contemporary-outfitted cabin w/ an unparalleled view! 5 mins to Ascutney mountain - an outdoor enthusiast’s dream w/ 45+ miles of mountain biking, hiking & running trails. Dine on the 1,300 sq ft deck while taking in the majesty of the mountain. Relax in the hot tub, roast marshmallows in the fire pit or star-gaze w/ our binocular telescope at night. 25 mins to Woodstock! 45 mins to Killington! Your Vermont getaway awaits… *1 dog max for $200/stay

Tiny Modern Cabin | Fire Pit Evenings | Ski Access

Our 1 bedroom, 1 bathroom cabin pairs a queen loft with a queen pullout couch and a bright, modern feel. • Private patio with a courtyard, outdoor seating, and a Solo Stove fire pit • Fully equipped kitchen with upscale appliances, dining table, and washer/dryer • Dedicated workspace, Wi‑Fi, and board games for easy downtime • One pet (25lb limit) is welcome to join you on this adventure Settle in and enjoy the fire pit, the patio, and the easy trail access when you’re ready to book.

Custom cabin on Mt Ascutney, with faraway views

Combining sweeping views of distant hills with privacy and wraparound porches, the Red House is a custom cabin built for couples and smaller families getting away from busy lives. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont. It awaits the discerning traveler who can do absolutely nothing, yet experience it all!

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Modern Cabin | Calm Retreat | Easy Outdoor Access

Welcome to our 2-bedroom, 1-bath modern cabin at Ascutney Lofts, where clean Scandinavian-inspired design meets a peaceful Vermont setting. • Private backyard with outdoor furniture, BBQ grill, and a fire pit • Open living space with room-darkening shades and a dedicated workspace • On-site washer and dryer plus a full kitchen and dining table • Mt Ascutney State Park and local covered bridges are a short drive away Settle in, cook, and unwind with an easy, nature-close stay.

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.

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)

Peaceful Vermont Cottage w/ Outdoor Sauna!

Escape to this cozy chalet-style home in Vermont’s tranquil woods, just 15 mins from Woodstock - with wood powered sauna! Perfect for outdoor fun—hike or bike Mt. Ascutney or Mt. Peg - Skiing at Saskedena 6, Killington and Okemo. All within a 30 minute drive! Come home to a wood powered Sauna waiting for you! Tucked at the end of a private road, it offers peaceful seclusion with easy access to nearby Woodstock and Windsor. *note - non operational fire place*