
Vacation 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!

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.

CozyCub- Location, Fireplace, Ski Off/Shuttle On!
Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

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!

Ski home to Trail Creek!
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!

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…
This rustic Mountain Green Resort condo offers easy access to ski/mtn bike lifts with resort style amenities. Features include 4K Smart TVs, High speed WiFi, private balcony with mountain views, board games, and full kitchen. On-site health spa including pool, sauna, hot tub, gym, masseuse. Restaurants and nightlife are minutes down the road. Restaurant/bar and ski/rental shop also within resort. Free shuttle to lifts available during ski season.

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!

Renovated unit, prime location! Shuttle on/Ski off
We are located in Killington, VT. A newly renovated family friendly condo complex located on East Mountain Rd. Take the free shuttle (modified schedule post Covid) and end your day by skiing back to the condo. In the summer season you can enjoy a day mountain biking and ride home in just under five minutes. Enjoy the outdoor pool during the summer after a day of mountain biking! Year round activities all within a short distance.

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!

Renovated 1BR, 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. 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.

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!

Hotel Chic - Home Comfort -Ski Easy.
HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS OUR ULTRA COZY RETREAT WAITS JUST FOR YOU LOTS OF SNOW HERE! C’MON❄️ ⛷️ 🏂Pico-5 minutes ⛷️ 🏂Killington-15 minutes ❄️❄️SUPERHOST RATED❄️❄️ ❄️Squeaky Clean ❄️Fireplace, WIFI ❄️TV in living room & bedroom ❄️Private covered porch ❄️Keypad check in ❄️Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.
Popular amenities for Rutland County rentals with a pool
House rentals with a pool

Ski-In/Ski-Out Hike Okemo Mountain Condo

Ski On/Off Sunrise at Killington

Entire Home, Near Slopes, Hot Tub, EV Charger

Luxe 4BR w Incredible View & Game Room!

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Peaceful condo at Okemo - Direct Ski Access

Luxurious family retreat home in the mountains

Luxury Ski & Summer Trail Creek Condo
Condo rentals with a pool

Walk to Lifts * Hot Tubs & Pub * Sleeps 4

Bright & Cozy Ski-in Condo with Mountain View

Location + Spa! - Cozy 2BR Condo - Mountain Side

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

Powder alert lets go Cozy 2 Bedroom .2 mi to mount

Mountainside 2-BR Ski-In/Out Okemo Haven

Updated large condo across from AT and skiing

1BR Ski-Home Pool/HotTb, Walk 2 Lifts, golf
Other vacation rentals with a pool

Killington/Pico Condo, Cozy Family/Friend Getaway

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Newly renovated condo-The Woods

Killington Vermont Luxury 2 bed condo

Ski-in / Ski-out 3BDR+ Killington Condo at Sunrise

Cozy Killington Condo

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Ski, Ride, Walk On/Off Condo On Pico at Killington
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- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Lake George Expedition Park
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- Dorset Field Club
- Whaleback Mountain
- Fox Run Golf Club
- Autumn Mountain Winery
- Ekwanok Country Club
- Montshire Museum of Science
- Northeast Slopes Ski Tow
- Gooney Golf
- Things to do Rutland County
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