Vacation rentals in Jenningston

Mountain Time - with views of Timberline

Take it easy at this unique and tranquil getaway. Located in Canaan with deck views of the Windwood airstrip and the slopes of Timberline. We are just minutes drive to Thomas, Davis, Blackwater Falls, Timberline Resort, Canaan Valley Resort, Dolly Sods. You name it, you are here. The townhome features, 3 bedrooms, 2 full baths, a fully equipped kitchen, bright and airy rooms, an unfinished basement with washer, dryer, and plenty of storage for your mountain bikes, ski equipment, etc. Enjoy!

Stunning Nordic Modern Cabin on Five Idyllic Acres

A fantastic, architect-designed, Nordic-modern, four-bedroom, two-bath cabin, tucked away down a relatively secluded dirt road in the community of Old Timberline. Flat lot, surrounded by beautiful tall trees. Walking distance to miles of trails and the Canaan Valley Wildlife Refuge. Easy access from within the neighborhood to the Dolly Sods Wilderness. Minutes to White Grass, Timberline Mountain, and Canaan Valley ski resorts. Or just explore the wooded wilderness behind the cabin!

Lab’OUR’ of Love Lodge. Luxurious, Rustic & Unique

Solar powered 2BR (2 king, Queen sofa bed in loft, & queen blow-up) true log cabin that’s central to Timberline, Canaan Valley, Dolly Sods, Seneca Rocks, Spruce Knob, Black Water Falls, & more! Beds have luxury mattresses & sheets. Exteriorly, there is a wrap-around deck w/ hot tub, 360 degree views, & tame wildlife. Interiorly, the living room has a real stone gas fireplace, live edge walls, full kitchen, & fireplaces in BR’s. Escape to peace & quiet & stay connected w/ Starlink Wifi.

Cozy Camper on the Rail Trail

Unique, dog-friendly camper-to-tiny home conversion. Wake up to amazing views with mountains in every direction. The Allegheny Highlands rail trail greets you as you step out the front door. No pet fees! Perfect for those looking for a peaceful and safe location, just off the beaten path. Surrounded by the Monongahela Forest, and the Cheat River, this valley is an outdoor recreation paradise. Rustic and simple, the guest house offers you what you need for a comfy stay.

The Hideaway- An Amazing and Serene Mtn Escape

COZY, MODERN, CLEAN cabin in the woods. PRIVATE, great VIEWS, by trails. New kitchen appliances. EV charger (J1772). Built in 2023. 3 bedrooms (COMFY Kings + Queen), 3 full baths + 2 living rooms. Lots of windows let in natural light and beautiful views of the Valley. DECK with GAS GRILL, Good WiFi (upload 25 download 300 MBs), wood-burning stove. EASY ACCESS year-round, even in winter! Close to Davis, Thomas & short drive to Timberline, Canaan Valley, & White Grass ski resorts

Creekside Canaan Cabin - pets free, L2 EV charger

Known to locals as "Kate's Place" after the old postmaster, this home has been a village gathering place for nearly a century. Updated in 2022, this home has the quirky charm of an old mountain cabin with modern features, such as a brand new, fully stocked kitchen and Level 2 EV charger. No pet fees! Enjoy the solitude of the woods, the mountain views, and the trickling creek out your window. Dolly Sods, Canaan Valley, Timberline, and White Grass are all within a 15 minute drive.

Basement apartment in the middle of the valley!

This is a basement apartment in the heart of Canaan Valley. Less than 10 min drive to everything: Timeberline ski resort, Canaan Valley ski resort, incredibly fun local XC ski area Whitegrass, art galleries, amazing food options, breweries, and even distilleries! There are two state parks to hike and explore within 10 mins, and a beautiful wildlife refuge only one mile away. Whatever outdoor recreation you enjoy, Tucker Co has the best places to explore. And high speed WiFi.

Red Spruce Rental

Welcome to Red Spruce Rental, a cozy 2nd-floor apartment in Davis, WV. With two bedrooms and a well-equipped kitchen, this retreat is just two blocks from local shops, boutiques, and breweries. Explore the artsy charm of nearby Front Street in Thomas, and enjoy quick access to Blackwater Falls State Park and top ski areas like Canaan Valley, White Grass Nordic, and Timberline Mountain. Local art and photography decorate the space, making it a warm and inviting getaway.

Scenic View - Hot Tub - Pet Friendly

Our cozy 4-bedroom, 3-bath townhome is perfect for your family getaway! Centrally located, it’s just minutes from Timberline Mountain, Canaan Valley Resort, Blackwater Falls, and scenic hiking trails. After a busy day, unwind on the back deck, relax in the hot tub (added Nov ‘25), or stargaze under the clear mountain skies. With remodeled bathrooms and a newly finished basement, the home has been transformed into a spacious retreat that comfortably sleeps 9.

Winter Wonderland Skiers Dream CanaanValley!

LOCATION LOCATION. Private fishing pond! KIDS and Adults LOVE TO CATCH! Central Cortland Rd. One block to Canaan Valley BBQ, Canaan Valley Store, New Miniature Golf, Trail Labs. 3.8 Miles to Timberline Mountain. HEATED 2 Car Garage! VIEWS FULLY RENOVATED DECEMBER 2022. ALL NEW HICKORY HARDWOOD FLOORS, BRAND NEW GOURMET KITCHEN with HUGE island. LARGE BRAND NEW HOT TUB ON PRIVATE BACK DECK. HUGE BONUS ROOM WITH LARGE FUTON AND FOOSBALL TABLE.

Old Post Office - fam/pet/EV friendly w. king bed

Come gather at our hideaway! 7 minutes to Canaan Valley, 20 minutes to Blackwater Falls or Thomas, and within easy day-trip distance for lots of wilderness. Just outside the southern tip of Canaan Valley State Park, our ca 1900 home is close to tons of outdoor activities! There's a well equipped chef's kitchen. Enjoy TV, break out the board games, or spin a record. Ours is a comfortable destination to travel with family or pets. Welcome!

Modern cabin in Dolly Sods w/ sauna & EV charger

A bright, modern cabin in the heart of the Monongahela National Forest. This brand new design driven space feels like being in a treehouse. It lies at the edge of the Dolly Sods wilderness, has forest views from every room, and a sauna. The location provides easy access to tons of hiking and is only 2.5-3 hours from Washington DC. It's as close as you can get to Dolly Sods without camping! 4WD needed in the winter.