Vacation rentals in Chester

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 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

The Owl’s Nest in Landgrove

Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

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.

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!

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

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.

Cute studio apt on historic VT farm

Spend some time on a historic farm in Southern Vermont. Visit with pigs and chickens, walk around on country roads, take a dip in swimming holes, wildlife abounds! Super-relaxing setting in beautiful Mother Nature and well-equipped accommodations with everything you need. The self-contained little studio has a separate entrance. Full kitchen and bath, queen bed plus a roll-out twin. Excellent heater. Starlink wifi.

Quaint stone house!

⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!