Vacation rentals with a pool in Rutland County

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!

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS OUR ULTRA COZY RETREAT WAITS FOR YOU. MINUTES TO SEASONAL EVENTS, WEDDINGS, HIKING, MOUNTAIN BIKING, GOLF, PRIVATE POOL - JUNE/SEPT EASY ACCESS TO AT/LT. Pico-5 minutes Killington-15 minutes SUPERHOST RATED Air conditioned Fireplace, WIFI TV/living room & bedroom Adjustable queen bed Private covered porch Keypad check in Smoke free/Pet free Seasonal private pool NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children/pets.

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.

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Pool and Spa area closed May 4 to May 15 for annual Maintenance

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space. Pool and Spa area closed 5/4-5/15 for maintenance

Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym

Ahoy, ski enthusiasts! "Jack S'Bearo" - a renovated 1-bed, 1-bath on Pico Mountain, VT, offers an exhilarating ski experience steps from the lift and a shuttle to Killington Resort. The new kitchen, wood-burning fireplace, and balcony make it a haven for relaxation. This ski on/ski off treasure boasts a cool design for easy access to the slopes. Grab your gear from the ski locker, step outside, and set sail to the lifts. Make "Jack S'Bearo" your pirate's cove, where adventure meets comfort!

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Big Pool, Golf we are on the course 2 Bedroom

Come enjoy this peaceful retreat, a warm fire and ski-in trail (depends on snowfall) with beautiful Mountain views! Our cozy 2 bedroom 1 bath is nestled away right on the golf course near Snowshed; Minutes away from ski lifts, restaurants and night life. Enjoy a warm space by the fire after skiing, snowmobiling, tubing and shopping! Shuttle every 30 min weekend & holiday weeks- Common laundry room -free washer/dryer Ski Locker- Pool heated in the summer Enjoy the Beast of the East!

SKI ON/OFF Spruce Glen C | AC | Fireplace | Sauna

Come and enjoy the largest private trailside property in Killington (almost 4 acres), with more convenience and value than large house rentals and more privacy than condo villages. The direct ski on/off is the easiest you'll find in Killington. Quiet and serene, the mature New England Evergreens and gentle mountain stream are a tranquil relief. An ideal ski in ski out or any season vacation getaway. Great Eastern is the longest green run in the East. Welcome to Spruce Glen!

Vermont Horse Farm

Enjoy a morning cup of coffee on the patio overlooking the horse pastures or an evening by a fire under the gazebo with a fire pit on this idyllic Vermont horse farm with glorious views. Close to many activities, such as hiking, skiing and swimming. Scenic retreat on a family owned and working farm. Here we have horses, donkey, chickens, goats, and of course our dogs and cats. There is a short hiking trail with beautiful views and a picnic table by the stream.

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!

AC | Dog-Friendly | Bike, Hike & Relax

Escape to the quieter side of Killington. Spring and summer are some of the best times to visit—fewer crowds, lower rates, and easy access to hiking, biking, golf, and everything the mountains have to offer. After a day outdoors, relax on the private balcony, unwind by the fireplace, or enjoy the resort amenities just minutes away.