Vacation rentals with a patio in West Windsor

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Top-rated patio rentals in West Windsor

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Guest favorite

Home in Windsor

5.0 out of 5 average rating, 54 reviews

Modern custom home on a side of Mt Ascutney

Beautiful views and an impeccable setting define this stylish house on a flank of Ascutney. It has a luxurious master suite, and a bedroom with 2 twin bunk beds. Woodstock village, Okemo, Killington and Sunapee, and the Upper Valley are a quick 20 to 40 minutes. The Brownsville Butcher and Pantry and Ascutney trailheads for hiking/snowshoeing are next doors. The Harpoon Brewery, and backcountry skiing are close by too. This recently built home home offers something for everybody in all seasons.

Jan 1 – 8

G$84,411 GYD per night

Guest favorite

Guesthouse in Reading

5.0 out of 5 average rating, 11 reviews

Peace & quiet at Comet Farm

Get your second wind at Comet Farm. Nestled amid rolling hills and sprawling meadows, this retreat sits between Woodstock and Okemo Mountain, a setting for hiking, cycling, skiing, family outings and moments of self-discovery. As the sun bathes the landscape in warm hues, the expanse of big skies will leave you awe-inspired throughout the day, while the night unveils a breathtaking canvas of bright stars. Awaiting you are Vermont experiences such as antique stores, farmers markets and breweries.

Oct 24 – 31

G$66,465 GYD per night

Guest favorite

Tiny home in West Windsor

5.0 out of 5 average rating, 13 reviews

Red Barn Cabin

Our cozy modern cabin is anything but ordinary, nestled amidst the pastoral landscapes of Brownsville, Vermont. Moments from world-class skiing resorts, pristine hiking trails, and thrilling biking adventures, this is your passport to a truly memorable getaway. Short stroll from Brownsville Butcher & Pantry, and a quick 20 minute drive to the Upper Valley makes it ideally located to area's best. Book your stay today, and let the magic of Vermont, captivate your soul. Your dream vacation awaits.

Jun 5 – 12

G$31,614 GYD per night

Guest favorite

Cabin in West Windsor

5.0 out of 5 average rating, 19 reviews

Cozy Log Cabin w/ Incredible Mountain View

Plan your summer 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 telescope at night. Within 30 mins of Dartmouth College, Woodstock & Quechee Gorge! Your Vermont getaway awaits… *1 dog max for $150/stay

Sep 11 – 18

G$131,719 GYD per night

Superhost

Home in West Windsor

4.8 out of 5 average rating, 10 reviews

Chuck's Place

Spring and summer are the best seasons in Vermont! Chuck's is a stand alone house dedicated to vacation rentals. Private and pristine. Situated overlooking Mt Ascutney, an easy walk to the village of Brownsville with our infamously amazing Brownsville Butcher & Pantry for the foodies. You're an easy drive to Woodstock, VT and Hanover, NH. Come for the many recreational events happening all summer. Trail runs! Biking! Balloon fest! Horse events! Or sit on the deck, relax and take in the view!

Dec 11 – 18

G$51,635 GYD per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 131 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

Sep 18 – 25

G$20,767 GYD per night

Guest favorite

Loft in Mount Holly

4.87 out of 5 average rating, 46 reviews

Mapleside Escape: Sugar/Ski house

Your Mapleside Rustic Retreat awaits! This gem is nestled amidst the picturesque landscapes of southern Vermont and only a 12 minute drive to Okemo/Jackson Gore, 35 minutes to Killington/Pico. If the season is right it offers the unique opportunity to see some pure VT maple syrup being made! Skiing, snowboarding, hiking and mountain biking trails await, making this spot an ideal base for year-round fun. Come explore nearby towns which offer charming shops, dining, and cultural experiences.

Sep 4 – 11

G$24,053 GYD per night

Guest favorite

Cabin in Londonderry

4.96 out of 5 average rating, 105 reviews

Summit view cottage:Private summer cabin w/hot tub

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 6 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn. Very close proximity to the town of Manchester, which has great shops and restaurants.

Apr 16 – 23

G$84,339 GYD per night

Guest favorite

Townhouse in West Windsor

5.0 out of 5 average rating, 44 reviews

Lovely Trailside 2 Bedroom Townhouse

Enjoy a fun outdoor adventure at this centrally-located condo on Mt. Ascutney. Trails are just outside the door, with miles of back-country skiing and snow shoeing, including Ascutney Outdoors lodge, lift-assisted tubing/sledding, and beginner skiing (t-bar). Maple Kitchen restaurant and Brownsville Butcher & Pantry are within a mile. Great sporting, shopping, eating and family activities nearby at Okemo, Killington, Woodstock, Hanover, Harpoon Brewery, King Arthur Flour and more.

Nov 5 – 12

G$50,477 GYD per night

Guest favorite

Home in West Windsor

4.96 out of 5 average rating, 56 reviews

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.

Jan 12 – 19

G$29,283 GYD per night

Guest favorite

Condo in Ludlow

4.93 out of 5 average rating, 55 reviews

Ground Floor, Okemo True Ski-in/Ski-Out

Put your gear on the patio and just walk out to the slopes! Okemo Mountain Lodge ground floor unit. C-building is the closest property to the A-Quad/B-Quad lift. Come enjoy convenient skiing, free parking and fast internet. Ski school gathers right outside the patio. How convenient it is to make your own meal during a powder day! Please note there is no AC at this condo complex summer time. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Jul 21 – 28

G$21,002 GYD per night

Guest favorite

Cabin in Windsor

5.0 out of 5 average rating, 24 reviews

Charming Cabin in Central VT

Charming cabin close to many wonderful attractions in VT and shopping in NH! We love our quaint cabin and would love to share this magic place with you! Come make memories with your family in the winter or the summer, our cabin is the perfect place to relax by the wood burning stove after a long day skiing/snowmobiling or make some hotdogs at the fire pit after mountain biking, hiking, kayaking all day long!

Apr 1 – 8

G$47,293 GYD per night