Holiday rentals with a pool in Windsor County

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

3 bedroom townhouse with 2 full baths. Third bedroom is an open loft with 2 twin beds. The Woods is a luxury condo development located 3 miles from the lifts at Killington. Pool, gym and spa facilities. New for Winter 2024/25: Killington Cafe & Wine Bar at the The Woods! 6 guests max per law. ONE well-behaved DOG upon approval (NOT 2 DOGS); $90 pet fee per stay. *INCLUDE YOUR PET AS A GUEST AND TELL ME ABOUT YOUR DOG WHEN BOOKING. Sorry, NO CATS. Summer guests, NO A/C in the unit.

NEW Killington Studio: Great Location! Comfy. 431

Welcome to our Killington studio, perfect for skiing, biking, hiking, antiquing, beer tasting, kayaking, exploring, or simply unwinding. This hotel room-style condo sleeps four in two comfortable queen beds. Enjoy cable/streaming on the large smart TV. Amenities include a mini-fridge, microwave, Keurig & coffee maker. The full bathroom offers a tub & shower. Outside, a heated pool awaits (open June to mid-September). You'll love it! (Note: This unit is hotel-room style without a kitchen.)

Updated Dog-Friendly/Free Shuttle/Across From Lift

Step into comfort and convenience with this beautifully renovated 1BR/1BA condo, nestled in the main Mountain Green building #3. Offering a cozy, dog-friendly environment, it’s perfectly situated across from Snowshed and Ramshead lodges, giving you effortless access to both winter and summer activities. A free shuttle service stops in front of the building during the winter months. The condo boasts modern updates throughout, ensuring a stylish stay. A true getaway for all seasons!

Historic Home on 17 acres of land. Go escape!

This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool will be reopened around May 2025! It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything just ask!

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

#45 Luxury Ski & Summer Condo with Private Sauna

Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

Exceptional Retreat, ski, hike, bike, adventures

This is a 2 bedroom,1 bath condo in building 1. It is on the top floor so you have beautiful views and no noise above you. It is quiet and comfortable. The indoor pool, hot tub, sauna, steam, and spa are open. We are open from Thanksgiving to Easter. The outdoor salt water pool is open from Memorial Day till Labor Day. There is also a key for an outdoor locker for skis. Parking is plentiful and there is an elevator in the building.

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

Penthouse Retreat • Stunning Views Walk to Slopes!

Escape to a stunning penthouse retreat with rare dual views of Killington’s slopes and peaceful valley. Just steps from the lifts, it’s ideal for skiers and après-ski lovers. After a day on the mountain, unwind with premium entertainment, a hot tub, steam room, infrared sauna, and indoor/outdoor pools. Designed for comfort and relaxation, this one-of-a-kind getaway promises an unforgettable stay. Book now!