Holiday rentals with a hot tub in Pittsfield

Romantic Treehouse- PVT Hot tub, 20 Min to KLT

This unique treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows and custom bathroom/kitchen. My grandparents once owned and operated a dairy farm on the land. I want to share the treehouse and surrounding area with my guests. Located on the historic Rt 100 ski highway with easy access to Killington/Pico (20 min), Sugarbush (40 min) & Okemo (45 min). Private salt water hot tub directly under treehouse, new in 2026!

The Birch Perch! Treehouse with spa and fire pit!

Romantic Honeymoon or fun family fantasy come true this treehouse has it all! Built by The DYI Network Treehouse Guys! Every detail custom crafted in this home in the tree tops makes your ultimate Vermont experience. All just 8 minutes to the lifts at Sugarbush. Kitchenette, cast iron stove, clawfoot tub, washer/dryer, AC, & outdoor shower all encased in a whimsical perch near skiing, waterfalls, biking and hiking. Incredible hillside views from your private deck! Romantic Hot tub in the trees!

forest retreat; off-grid writers cabin

Secluded rustic charm, circa 1900 cabin in the woods getaway, spend time in nature surrounded by forest, brook, wildlife, hiking trails, fall foliage, mountain biking skiing. Sauna, Cold Plunge, Outdoor Shower & Hot Bath (seasonal) Unwind from the outside world and reconnect with your self or your loved ones and the natural world around you. Loft with real beds, well stocked kitchen, grill, outhouse, Glamping! Close to Woodstock, VT and Killington, S. Royalton, White River, Lebanon & Hanover NH

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski is a modern Killington home located just off the main road and close to everything. While you relax at our home after a day on the mountain, you can catch a movie on one of our smart TVs, relax in the outdoor hot tub, roast s'mores at the fire pit, enjoy a drink at the motorcycle bar, shoot hoops in the game room or sit by the wood burning fire. This home is perfect for groups and families to spread out and enjoy all that Killington has to offer. Central AC - rare in Vermont!

Camp Poe: HotTub/AC/Game Room/6acres/Patio/EVchrgr

Experience the heart of the Green Mountains on our private 6 acre estate. Camp Poe at Estabrook is the ultimate Vermont getaway--wide plank floors, fully stocked farmhouse kitchen, wooden beams and a two story family room w/ a wood burning stove. This 3200 sq ft house is perfect for entertaining with two separate living rooms, bar, game room, 10ft dining tables (inside AND outside) and hot tub. 13 min to Killington Mtn & 4min to the #1 golf course in VT! EV Charger available for guest use.

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

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.

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Dog heavenly! Private, beautiful and relaxing.

Bright, secluded, second floor one room suite with private bathroom overlooking Mill River and across a covered bridge. No neighbors visible, but near town. Fly fish in the back yard, sit around the firepit, enjoy fall foliage, and hike and ski. Swinging bridge and Appalachia long trail very nearby. Close to three ski resorts: Killington, Okemo, and Pico. Dogs are welcome and loved, with plenty of room to run. Comfortable queen-sized bed and couch.

Moonlight Farm Studio · Hot Tub · Vermont Retreat

Welcome to Moonlight Mountain Farm — a peaceful Vermont farmstay. Unplug and recharge surrounded by woods, fields, and mountain air. This private, open-concept studio retreat is designed for couples or small groups seeking quiet, comfort, and a true rural escape — featuring an indoor hot tub, pond and mountain views, and optional outdoor sauna. Whether you’re here to ski, hike, bike, or simply slow down, this is your place to reset.

Newly renovated ski retreat at Killington

Located at Mountain Green Resort, Building III. Walk to Snowshed Lodge to begin your day of skiing, or take the free shuttle that will pick you up outside the entrance. After your day of skiing ends and you return to the unit, to experience the many amenities that the resort has to offer: indoor pool, eucalyptus steam room, two spas, sauna, fitness center,. You may prefer to stay in the unit and watch skiers come down the mountain.