Vacation 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.

5 min Ski| 1 min Nightlife| Hot Tub| Arcade| Fires

Nestled in the heart of Killington, our 4 BR/2 BA cozy retreat for anyone seeking a peaceful getaway! Gourmet kitchen, perfect for preparing meals together. Open-concept living w/ ample room for quality time. Bedrooms thoughtfully designed to ensure a restful night and flexible sleeping arrangements. Unwind after a day on the mountains with our rain showers & heated floors or outdoors in our relaxing Hot Tub oasis. Dry your gear with our heated gear dryer. Make memories and book today!

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!

Luxury Ski Cabin, 2 bedrooms, den & 3 bathrooms

This luxury residence on Killington Mountain is a 400-yard walk to the closest ski trail or a short 5-minute drive to the principal ski bases, along with the resort's array of bars, eateries, and retail outlets. It features an indoor jacuzzi, a spacious living/kitchen area bathed in natural light. A variety of summer pursuits, including golf, hiking, mountain biking, and canoeing, are conveniently accessible within minutes from the home. Plus, the property welcomes pets.

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!