Holiday rentals with a pool in Windsor County

Comfy ski in/out studio at base of Pico-Killington

Studio at the base of Pico with a balcony. Free shuttle service from my place to Killington, which is 10 minutes away.Brand new sofa bed with a pillow top. Room divider. Lots of TV channels with Xfinity. Luggage cart and elevator for easy access. Fast Wi-Fi. Free ski locker with one key for each guest. There is a laundry room with coin operated machines. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for one day. No daily cleaning service. No parties. Free parking

Ski Mountain View Estate

Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Always plenty of firewood for the pit! Pool is closed for winter

Updated large condo across from AT and skiing

Family friendly, large 3 bedroom condo across the street from hiking and skiing in Killington. WiFi, cable TV, large gathering areas, spacious bedrooms, updated kitchen, and unlimited free firewood in winter. Plenty of après-ski chic touches make this a stylish yet comfortable retreat. 2 minute drive to Pico, 2 min walk to Appalachian Trail! Whether skiing, hiking, playing tennis, swimming, or game nights and cooking at-home meals with friends, this updated condo is a perfect spot to get away.

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Our condo is minutes from Pico & Killington! 🥾AT&LT, 💍wedding venues, 🚴‍♀️mountain biking, ⛳️golf and many seasonal local events Superhost level comfort welcomes you! OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from LT/AT •Squeaky Clean •Fireplace, TV, WIFI •Seasonal Pool(towels provided) •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21yrs)

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

New 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. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

Updated Dog-Friendly/AC/Across From Mountain/Pool

Experience comfort and convenience in this renovated 1BR/1BA condo in Mountain Green building #3. Dog-friendly and ideally located across from Snowshed and Ramshead lodges, it offers easy access to year-round activities. The condo features an open floor plan with a spacious living area, a fully updated kitchen, and modern finishes throughout. A free shuttle service stops at the building in winter. With all the amenities you need, this stylish retreat is the perfect getaway for all seasons!

Renovated 1BR, Walk to Lifts, Covered parking

Our comfortable 1-bedroom condo in Building 3 of the Mountain Green Resort provides a bright yet cozy home base for your Killington getaway. Our condo features a new kitchen, dedicated Wi-Fi, and smart TVs. Conveniently located within walking distance to Snowshead, it's perfect for all your mountain activities. The shuttle runs daily through the winter season. The indoor pool, hot tub, and gym are open daily. The outdoor pool is open Memorial Day through mid-September.

Serene Top Floor Condo (resort style amenities)

Welcome to Killington! We offer a year round accommodation with the convenience of walking to the lifts, free covered parking, private balcony, full kitchen, and 24/7 keyless entry. The Mountain Green condos have great seasonal amenities in our building such as indoor/outdoor pool, hot-tub, fitness center, ski rental , full service bar/restaurant, outdoor lockers. This is the ideal setup for anyone enjoying the mountain without driving to it!

Cozy Condo- Close to Mountain, Ski home trail

Experience Killington like never before with our ski-home condo and a free 5min shuttle ride to the mountain on winter weekends. Our home is the perfect location to experience all that Killington has to offer. It has a free shuttle and a ski home trail. As well as quick and convenient access to Killington's great nightlife including restaurants, shopping, bars, and entertainment.