Holiday rentals with a patio in Windsor County

Curious Little Cottage

Our cozy cottage is nestled on a quiet dead end road, conveniently located to fabulous area attractions, such as ski areas, golf courses, historic landmarks, good eats, bike trails, scenic roads, lil swimmin holes, art gallerys, live music, Paramount theater.. you wont be bored! Heidi Ethan & Heather (your hosts) have decorated our cottage with fun & interesting decor which we think will make for a fun and interesting getaway!!! As much as we love them...We have a very strict no pet policy!

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mountain views, peaceful brook on 1+ acre property. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV.

Chuck's Place

Chuck's is a neat and tidy stand alone home dedicated to vacation rentals. Fully stocked! Private and convenient on 7 sunny acres overlooking Mt Ascutney. Plenty to do out your door- hiking, snow-shoeing, skating, sledding, skinning and family-friendly skiing over at Ascutney. Brownville Butcher and Pantry is an active gathering place in the village. The best meats and fish anywhere! More downhill and cross-country/skate skiing, restaurants, pubs, and breweries all within 25 minute drive.

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo

Rent a "room" at an inn or rent this private B & B cottage. Romantic Retreat~Rest & relax! Unique tranquil getaway. Exclusive~A Bed & Breakfast Cottage for 2 adults. 1 BR & 2 BA. Rustic charm, generous modern amenities. King bed, 2 bathrooms, fine linens, living/dining area, galley kitchen, fireplace, hot tub, outdoor shower*, porch, fire pit, canoe*, & dog friendly! Killington&Okemo15minutesWoodstock 30 minutes-Ludlow 10 minutes Overlooks Lake Amherst. *Some features are seasonal.

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

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.

Addie's Place

A cozy and quiet space close to Dartmouth College (8 mins), Dartmouth Hitchcock Hospital (15 mins), and White River Junction Center (7 mins). You will have a private entrance to the space and access to a yard, a 3 season patio room, bedroom with a queen sized bed and queen pullout couch, a separate dining area, grill, and a private bathroom. There is no kitchen but there is a mini fridge, table, coffee/tea bar, plates, utensils, mugs, and a microwave.

Christian Street Condo with Screened In Balcony

Spacious Updated 2nd Floor Condo with a Screened in Balcony and Comfy Beds 10 min from Dartmouth Hitchcock Medical Center. 6 min from Dartmouth University. Whether you are looking to be close to ski resorts, you have a family member at DHMC, you’re working a job in The Upper Valley, or just looking for a centrally located accommodation in Vermont, this fully stocked, super clean and newly updated condo will comfortably suit all of your needs!

Cozy Riverside Vermont Retreat

Stay in our cozy home away from home in Bridgewater Corners, Vermont! Forget your worries in this spacious and serene space. Private residence with riverside access, close to Killington and Okemo mountain. Perfect for both for the simple relaxers or adventurers. Snowmobiling, golfing ,kayaking, natural watersource swimming, hiking, quiet historical towns, farmers markets, and much more. Book now and find out for yourself!