
Vacation rentals with a pool in Rutland County
Find and book unique homes with a pool on Airbnb
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!

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 so you can focus on business when not on the slopes

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.

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!

Lg Renovated Mtn View • Shuttle • Hot Tub • Xbox
Savor stunning mountain views from this oversized 1BR/1BA in Mountain Green Building 3—just a short walk or shuttle ride to Killington Resort and the tube park. Inside you’ll find a modern kitchen and bath, new flooring, cozy furnishings, plus an Xbox and arcade game. Best of all, the resort amenities are in the same building: indoor pool, hot tub, fitness center, ski shop, and restaurant. Ideal for couples, small families, or friends—your mountain escape awaits!

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!

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.

Right at Killington !
The only place closer to the Snowshed is the Grand Hotel. If you are young and agile you can walk to Snowshed Base - about 10 minutes. Welcom to Trail Creek Condo's. After the races enjoy indoor salt water pool or 2 hot tubs or hot sauna in the Trail Creek Amenities building (a couple of buildings away). Great for couples or families. We provide all linens, towels & firewood. FREE WIFI, cable and HBO. Fully stocked kitchen.

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. 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

Ranch at Mendon Mt Orchards

Ski-on/Ski-off Luxe 4BR with a view & game room!

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Trailside Vacation

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

Killington Vermont Luxury 2 bed condo

Bright & Cozy Ski-in Condo with Mountain View

Northlands at Trail Creek

Best value in this Cozy 2 Bedroom .2 mi to lift

Beautifully decorated condo with Sports Center I10

Killington Getaway 2bed/1.5 bath

#45 Luxury Ski & Summer Condo with Private Sauna
Other vacation rentals with a pool

Killington/Pico Condo, Cozy Family/Friend Getaway

Sweet Retreat

Cozy Killington Condo

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

Ski, Ride, Walk On/Off Condo On Pico at Killington

New Resort Condo Close to Lifts

Adventure Winter Ski & Spa Escape

Gateway A-10: Mendon Retreat. 2BR near Killington
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- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Mount Snow Ski Resort
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Lake George Expedition Park
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Dorset Field Club
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Gooney Golf
- Ekwanok Country Club
- Montshire Museum of Science
- Things to do Rutland County
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