Vakantieverhuur in Chester

Handmade 3 Bedroom Log Cabin | 5 Min From Skiing

Wake up to brisk mountain air with a cup of coffee and moose in the front yard... This house is a sanctuary, ideal for ski trips, hiking, leaf peeping, wine, beer, and cheese tasting, shopping and sugar house adventures. This is a place to unwind with friends and family. Sit in front of the cavernous fire place and watch the flames twist up the 18ft, handmade, stone hearth. With three private bedrooms, two bathrooms, a futon, and 10ft dining table, this house comfortably sleeps and feeds 8.

4BR-4BA/Fireplace/Near Skiing/Walk to Shops

Relax with your friends or family at this well-equipped and peaceful place to stay. Inquire about seasonal special rates. Located in a quiet, two home neighborhood walking distance to area shops and restaurants and a short drive to: Okemo (12), Bromley (17), Stratton (25), and Killington (27). Our home is perfect for a family or a group of friends. Open floorplan kitchen, dining, and living room, features a see-through gas fireplace inviting you to spend the evening after a day on the slopes.

Private Cabin 18mins from Okemo- "Pappy's Place"

Welcome to your peaceful Vermont escape. Nestled on 5 private acres in charming Chester, this hand-built log cabin offers rustic charm and modern comfort. It’s a place to slow down and reconnect with nature and family. With soaring 20-ft ceilings, an open-concept kitchen and living area, a lofted master, and two cozy main-floor bedrooms, it’s perfect for families. Enjoy peaceful nature, a firepit, and quick access to Okemo, Ascutney, hiking trails, and skiing in the beautiful Green Mountains.

Bread and Butter Apartment

Our house is located just a few minutes from Magic Mountain and less than thirty minutes from Bromley, Stratton and Okemo. Chester and Londonderry are a short drive away, and there are many wonderful hikes nearby. The apartment occupies the entire second floor of our house and has a private entrance. It includes two cozy bedrooms, a 3/4 bath, a small kitchen and a comfy living room. The apartment still has that old Vermont charm and is perfect for a relaxed weekend in the Green Mountains.

Vermont 1828 Reunion House, near Okemo

The Vermont 1828 Reunion House, close to Okemo is a spacious historic vintage ski lodge and farmhouse with 2 kitchens, 8 bedrooms, 4 baths, & a quintessential Vermont character. Excellent for gatherings & family reunions. Linens & towels provided, beds made. 10 acres, meadow & hidden pond. . A new automatic sprinkler system was installed in 2024 & the house complies with all safety regulations & certified by the town of Chester. Must be 25 years to rent. Long term rentals possible.

Charming Chester Farmhouse Near VT Slopes

Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!

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!

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain

Ideal to host up to 6 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of nature. Chester and Ludlow, VT are minutes away and call you to explore historic landmarks and enjoy skiing at Okemo Mountain (located 15 minutes away). With modern facilities & a private location, this will be your home away from home! New in June 2024 - we added a large outdoor patio equipped with a Jacuzzi Hot Tub, Fire Pit, and picnic table.

Sage House Glamping Retreat with Hot Tub + Sauna

Welcome to Sage House, a custom-built cedar tiny house surrounded by seven acres of natural landscape in beautiful southern Vermont. Stargaze from the comfort of your bed, forest soak in a private 2-person hot tub, unwind in the barrel sauna, relax by the firepit overlooking your private pond or explore the many outdoor activities in the area. Ski Okemo, Magic and Bromley. Snowshoe or hike local trials and waterfalls, and enjoy quaint shops + restaurants.

Lovely 2 Bedroom Apartment w/deck & pond view

The perfect Vermont getaway. Lovely new apartment behind retail store on main road to Okemo and Killington for winter skiing and summer adventure. Bedroom, living room, bunk room, fully equipped kitchen, laundry and mudroom. Large deck with pond view, easy access to vacation sites, mountain hiking and biking, discovering Vermont small towns. Experienced, welcoming Airbnb Super Hosts providing all the amenities for a comfortable stay.

Historic 150-Year-Old Farmhouse | Jacuzzi included

✨ Step into Vermont charm this fall. Our 1869 farmhouse is your cozy home base for leaf-peeping, scenic hikes, antiquing, exploring Chester, and crisp autumn days in the Green Mountains. Come home to warm up in the hot tub, roast marshmallows by the fire, and unwind beneath the stars surrounded by peaceful forest views. 🍂 Peak fall foliage right outside your door. 🍕 2-minute walk to pizza, pints, and live music (open Wed–Sat.)

Modern Cabin | Near Okemo & Chester

Escape to this beautifully renovated three-bedroom cabin set on three private acres in Vermont's Okemo Valley. Just minutes from historic Chester and a short drive to Okemo, Magic Mountain, and Killington, it's the perfect base for every season. Gather around the wood stove, enjoy peaceful mornings surrounded by nature, and spend your days hiking, skiing, or exploring Vermont's charming villages before returning home to unwind.