Vacation rentals in The Woods

Swirl Suite at Killington: Remodeled 2RM/2BA Suite

Luxurious 2RM/2BA condo in VT's Green Mountains, perfect for up to 6 guests. Features 2 queen beds, a queen sleeper sofa, ensuite bath w/ heated floors & multi-jet shower, open kitchen w/ island & dining table, gas fireplace, smart TVs, private balcony w/ electric grill, & shared washer/dryer. Enjoy discounted ski rentals, summer pool, shuttle bus access, high-speed WiFi, & easy access to Killington Ski Resort, hiking, golf, waterfalls, shops, & dining. Book your perfect mountain getaway now!

Modern 2 bed - 5 Min to Killington/Pico (NEW)

Newly listed, fully renovated 2BR ground-floor duplex for groups of 4 or couples. Just minutes to Killington lodges with a flat driveway for easy access. Guests enjoy exclusive ski and snowboard rental discounts and limited lift ticket deals. The modern interior features a mudroom, 75" TV, kitchen with butcher block island, whole house water filter. Two private bedrooms each feature Queen Nectar mattresses. Managed by Simple Vacation Rentals with 24/7 local support and digital Boarding Pass.

Starry Nights At KVR

GROUND FL 2 BEDROOM, 3 BATHS, SLEEPS 6.Our Condo is a 2 Bedrooms, 3 full Bathrooms; 1,327 sqft. Extra large living room-kitchen, dining area. Large windows, very bright, ground floor access. Master BR with King size bed, private bath, and washer/dryer closet. 2nd BR with two Queen beds, private bath. Living area with shower-6 shower heads, X-large shower made of tile and stone. Full kitchen, with full-size range&frig, microwave, Kuerig&Drip coffee maker, toaster, 3 Smart TV'S with Streaming.

Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym

Ahoy, ski enthusiasts! "Jack S'Bearo" - a renovated 1-bed, 1-bath on Pico Mountain, VT, offers an exhilarating ski experience steps from the lift and a shuttle to Killington Resort. The new kitchen, wood-burning fireplace, and balcony make it a haven for relaxation. This ski on/ski off treasure boasts a cool design for easy access to the slopes. Grab your gear from the ski locker, step outside, and set sail to the lifts. Make "Jack S'Bearo" your pirate's cove, where adventure meets comfort!

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Killington Tree House: 2 Room Modern Condo 432

Located less than two miles from the foot of the Killington Ski Area and recently renovated, this 2 room, 2-bathroom condo has a comfortable modern rustic feel. Relax after a long day on the mountain and warm your toes in front of the fire. Use the well appointed kitchen for preparing meals or head out to one of Killington's many fine restaurants. Enjoy the beautifully tiled kitchen and bathroom, with all the comforts and conveniences of home. We're also walking distance to many places.

The Overlook - Views | Hot Tub | Fire Pits | Games

Escape to stunning mountain views at The Overlook. Just 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of this private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. Convenient Level 2 EV charger compatible with all EVs at the chalet. 🏔️ Mountain View 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table ⚡️Level 2 EV Charger

Powder Hound - Modern, Heated Pool, BBQ, New Patio

Welcome to Powder Hound! A beautifully renovated mountain‑modern condo that blends upscale comfort with Vermont charm. Thoughtfully designed for relaxation, adventure, and everything in between, this 3 bed / 2 full bath retreat puts you minutes from world‑class skiing, hiking, night life and year‑round mountain fun. Enjoy a gas fireplace, smart TVs, updated kitchen, private patio w/ grill, & washer/dryer. Amenities include a heated summer pool, Wi-Fi, AC, & shuttle bus to base camp.

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Alpine Condo - AC & Pool - Golf & Bike

Updated 1-bedroom Whiffletree condo with stylish alpine feel—steps from Killington Resort, golf course, and access road. Thoughtfully stocked with essentials, plus a private gear locker for convenience. Relax at the onsite outdoor pool (open Memorial Day–Labor Day). Sleeps 4 with a king bed and queen pullout sofa. Portable AC unit in the living room helps keep the condo comfortable Pack & Play crib, mattress and sheets available upon request for $25 per stay. Reg #007718

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

Private Killington Retreat | Hot Tub | Fireplace

A cozy mountain hideaway with a private hot tub, stone fireplace, and exposed wood beams — this charming lower-level retreat is perfect for couples or small groups seeking a quiet Vermont escape. Minutes from Killington's hiking, biking, and dining, with a fully equipped kitchen and spacious sectional to decompress after a day outdoors. Peaceful wooded setting, self check-in, and a host with 8 five-star reviews across the property.