
Holiday rentals with a pool in Rutland County
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Top-rated rentals with a pool in Rutland County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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!

Jack S'Bearo - Slopes, Fireplace, Pool.
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.

Great Deal Cozy 2 Bedroom .2 mi to lift
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 B | Sauna | Fireplace | AC
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!

Hotel Chic - Home Comfort -Ski Easy.
HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS OUR ULTRA COZY RETREAT WAITS JUST FOR YOU. MINUTES TO WEDDING VENUES, GRADUATIONS, HIKING, MOUNTAIN BIKING, GOLF, SEASONAL PRIVATE POOL. EASY ACCESS TO AT/LT. Pico-5 minutes Killington-15 minutes SUPERHOST RATED Squeaky Clean Fireplace, WIFI TV in living room & bedroom Adjustable queen bed Private covered porch Keypad check in Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking
Our bright and cozy 1-bedroom condo in Building 3 at Mountain Green Resort is the perfect home base for your Killington getaway. Reserved parking spot in the garage. Walk to Snowshed Base Lodge or hop on the winter shuttle that runs every 15 minutes. Enjoy a renovated kitchen, dedicated Wi-Fi, and smart TVs for easy streaming. Resort amenities include an indoor pool, hot tub, sauna, and gym year-round, plus an outdoor pool from Memorial Day through mid-September.

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed
Ski On-Ski Off cozy mountain condo with Real Wood Fire Place and King Size Bed in Sunrise Village on Killington Mountain. Updates include all new furniture in the Master Bedroom & Guest Bedroom, all new top of the line Stainless Steel Appliances in the gourmet kitchen, Tastefully decorated Living Room with new queen size sleep sofa & matching chairs. Simply walk to the end of the parking lot to the Ski On/Off trail. I own the adjoining unit -more info below.

Trail Creek - ski home!
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!

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.

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails
Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!
Popular amenities for Rutland County rentals with a pool
House rentals with a pool

Peaks, pool & pure mountain air — book for summer

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

The Cocoa Command Center at Top Ridge: 4BR/4BA

Ski On/Off Sunrise at Killington

Topridge | Luxe 4BR w Game Room!

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Peaceful condo at Okemo - Direct Ski Access

Scenic 5 Bedroom Killington Mountain Vacation Home
Apartment rentals with a pool

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

Best skiing in yrs; reduced rates

Cozy Slopeside Studio at Pico

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

Charming 2-Bedroom Ski-In/Ski-Out at Jackson Gore

Modern Killington Farmhouse Condo: Close to Resort

Updated large condo across from AT and skiing

Amazing,Ski, Golf, Hike, Bike, Adventures
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¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Ski-in/out Jackson Gore Studio w/Kitchen

Newly renovated condo-The Woods

FUN 2BR/2BA Condo – Pool, Spa & Walk to Lift!

Adventure Winter Ski & Spa Escape

Historic 1850’s Renovated Farmhouse w/ Pool!

1BR Ski-Home Pool/HotTb, Walk 2 Lifts, golf

Killington Ski Gateway Retreat | 2BR Condo
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dartmouth College
- Montshire Museum of Science
- Emerald Lake State Park
- Adirondack Extreme Adventure Course
- Middlebury College
- Trout Lake
- Warren Falls
- Southern Vermont Arts Center
- Camp Plymouth State Park
- Things to do Rutland County
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