Vacation rentals in Pittsfield

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

Hot Tub|Sauna|Relax! 5 mins to downtown Killington

Welcome to your perfect Killington retreat! Our home offers the ideal getaway for relaxation & adventure. Unwind in the hot tub, rejuvenate in our outdoor sauna, or simply take in the stunning views that surround you. Located 7 miles, <10 minutes from Snow Shed & the slopes of Killington & <9 min to Pico Mtn, as well as an array of downtown restaurants, our home is the perfect base for your VT adventures. Once you experience the warmth & comfort we provide, you'll want to return again & again!

Romantic Retreat, Hot Tub, near Killington Mtn

This architect-designed, contemporary mountain chalet features all the classic elements – including stone fireplace with wood stove, soaring vaulted wood ceilings, walls of glass and wide pine floors. This stunning home has a lovely wooded backdrop adjacent to Hawk Mountain pond.   It is located in Pittsfield, 8 miles from Killington.   Kitchen has high-end appliances, quartz countertops and custom backsplash.    Stunning spa-like oasis bathroom. Several decks, fire pits, next to pond.

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! Winter: MUST have AWD/4x4 for winter access on dirt road and driveway. Snow tires recommend. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the beauty Vermont has to offer!

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

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.

Trailside Retreat: Hike & Bike From Your Doorstep

Airbnb Top 10% Guest Favorite. Ride & Hike 25 miles on the Green Mountain Trails from your door. Climb to Shreks Cabin for big views. Location: 5 mins to Green Mountain National Golf, 15 mins to Killington Resort. The Space: Modern retreat with stunning mountain views. Two separate living rooms offer privacy for groups. Amenities: River swimming access, ultra-fast fiber-optic Wi-Fi, and a secluded, quiet setting. Reliable, 5-star hospitality in the heart of Vermont

Skyeburst | Modern Mtn Home

| Welcome to The Skyeburst House | Reimagined 1970's Mountain Home 15 mins from the Killington K1 Gondola. This is a newly renovated modern home boasting lots of natural light, spa like bathrooms, open floor plan, and exposed cathedral ceilings. Curated with a mix of rustic and modern decor. High quality king and queen beds. Modern appliances. Samsung 75" QLED 4K TV. Sonos Sound System. Fire pit. Deck. Grill. Stars. Your Vermont adventure awaits.

Mountain Home with Scenic Views

A unique post and beam log cabin with beautiful scenic mountain views. 15 minutes from Killington and Pico ski areas. This one of a kind house offers an open floor plan with a great room and fireplace. Master suite has its own fireplace, jacuzzi tub and balcony. A loft area with pool table and tv . Outside hot tub with mountain views. Two car garage to park in on cold snowy nights. Large basement off garage makes getting out of your ski gear easy.

Killington area home - 4 seasons - hot tub and A/C

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, it's convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

Peak Hill – 3 Bedroom, Hot Tub. Car Charger!

Peak Hill is a 3BR, 2BA home on the Killington-Pittsfield border, just 10 mins from the slopes! Features include hot tub, mini-splits, cozy gas stove, smart TV, modern kitchen, spacious deck, & outdoor fire pit. Enjoy year-round fun: discounted lift tickets in winter. Easy access to Killington & Pico resorts, dining, & golf. No pets/smoking. (exterior cameras in place.) Book today & make Peak Hill your Vermont escape!

Green Mountain/Killington Getaway

Located in the charming town of Pittsfield Vermont, this comfy, quintessential Vermont home with a twist of modern sits amongst the trees on Hawk Mountain. With three levels and three bedrooms and a variety of bed sizes, this home can comfortably sleep 6 and offers room to spread out. All just 15 minutes to Killington or Pico. Golf, tubing, biking, hiking & kayaking all very close.