Vacation rentals with a pool in Ottauquechee River

Luxury Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Luxurious family retreat home in the mountains

An exquisite newly renovated country retreat nestled between the mountains on 30 acres. Pond, open pasture and woodlands to explore. Indoor infrared sauna with red light therapy. Spa bathroom with freestanding tub and two rain water showers. Organic bedding. Grand fireplace. Large open concept kitchen with top of the line appliances and 14 stage drinking water filter. Movie theater. Kids space. 3 bedrooms + loft Killington Skyship Gondola - 7 minutes Okemo - 25 minutes Woodstock - 20 minutes

Luxury Mid-Century Modern Vermont Home, Okemo View

The Brewster House is a premiere destination for skiing, hiking, enjoying the country or just lounging by the pool. Designed by renowned mid-century modern architect turned painter George W.W. Brewster, the Brewster House has been lovingly restored and updated, and filled with original, local art. With gorgeous views of Okemo and Hawks Mountain Wildlife Area, the Brewster House is close to incredible dining, great art galleries, and antique shops. Come bask in beauty and relax completely!

Cozy, clean studio with picturesque Vermont views!

Lovely studio in the heart of the mountains! Our cozy and well-lit space is perfect for solo travelers or couples looking to explore all that Vermont has to offer. Enjoy a queen-sized bed, pull out sofa, kitchenette and a charming bathroom, plus a beautiful new stone patio for relaxing outdoors. 2 miles to Woodstock and 1 mile to Saskadena Six. Experience local life with all the modern amenities you need for a memorable stay. In the winter months, 4 wheel drive or all wheel drive is mandatory.

Ski Mountain View Estate

Pool is open for the summer of '26 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. Great multi family getaway

Dana Road House Sunlit VT Country Home w/HotTub

Dana Road House: an idyllic 3BR/2BA VT country home Ideally located just 1.7 miles from Woodstock Village & 20 min. to Killington Skyeship. Gazebo with cedar hot tub, patio with dining , chiminea & BBQ Spacious open floor plan, chef's kitchen, 2 living areas, wood stove, Smart TV & WiFi. 3 comfortable bedrooms: a king master suite with jetted tub, queen room with brass bed and a double twin room. All amenities provided for your comfort & enjoyment. Follow on Social @DanaRoadHouse

Golf and Mountain Biking outside the door!

Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

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!

Luxury Container Home with Sauna & Heated Pool

Escape to a luxury modern container retreat minutes from Okemo Mountain. Set on 3 private acres with mountain views, this unique getaway features a sauna, heated plunge pool and thoughtfully designed modern interiors. Perfect for skiing, hiking, fall foliage, or relaxing in nature, the home blends comfort, style, and privacy while still being close to restaurants, lakes, golf, and everything Ludlow has to offer year-round.

Ski-In/Out, AC, Pools, Hot Tub, Pet-Friendly

Escape to a spacious, pet-friendly 1-bedroom mountain condo in Killington, comfortably sleeping 4. Enjoy year-round adventures with easy access to hiking, biking, golf, and skiing. The condo is 488 ft to the sunrise lift! Relax on your private balcony, by the gas fireplace, or at the resort's indoor/outdoor pools, hot tub, and fitness center. Perfect for a serene mountain getaway with all amenities.

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

Revel in this bright and modern ski condo just off Killington's main road and close to everything. Relax after a day on the mountain streaming on one of your 3 smart TVs. Indulge with the fabulous condo amenities including the pool, hot tubs, spa, gym, and tennis courts, or settle in by the wood-burning fire. Spread out in this spacious condo and enjoy all that Killington has to offer.

Private Farmhouse with in ground pool!

Escape to Your Vermont dream vacation… Nestled in the heart of Vermont’s picturesque countryside, this charming farmhouse offers the perfect blend of rustic charm and modern comforts! Book your stay at this private retreat with serene surroundings, and the ultimate luxury—a private in-ground pool for warm summer days and an outdoor fire pit for s’mores!