
Holiday 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.

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.

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 C | 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!

#45 Luxury Ski & Summer Condo with Private Sauna
Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

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.

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.

Cozy Condo- Close to Mountain, Ski home trail
Experience Killington like never before with our ski-home condo and a free 5min shuttle ride to the mountain on winter weekends. Our home is the perfect location to experience all that Killington has to offer. It has a free shuttle and a ski home trail. As well as quick and convenient access to Killington's great nightlife including restaurants, shopping, bars, and entertainment.
Popular amenities for Rutland County rentals with a pool
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Ski-In/Ski-Out Hike Okemo Mountain Condo

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

Ski On/Off Sunrise at Killington

Entire Home, Near Slopes, Hot Tub, EV Charger

Okemo Condo – Ski In/Out

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Peaceful condo at Okemo - Direct Ski Access
Apartment rentals with a pool

Luxury Condo - with Garage Parking and Pool

Bright & Cozy Ski-in Condo with Mountain View

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

Great early skiing Cozy 2 Bedroom .2 mi to mount

Killington Getaway 2bed/1.5 bath

Walk to lift, Ski home, Sunny with loft

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

3BR Ski in/out from top A/B lift, pool & hot tub
Other holiday rentals with a pool

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

Newly renovated condo-The Woods

The Woods Renovated 1BR Studio close to the slopes

Cozy Killington Condo

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

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

New Resort Condo Close to Lifts

Okemo Ski Condo, Steps from Trails. Modern & Cozy
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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
- Lake George Expedition Park
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- Whaleback Mountain
- Dorset Field Club
- 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
- Food and drink Rutland County
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- Nature and outdoors Vermont
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