
Holiday rentals with a pool in Chittenden
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chittenden
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!

Ski-on/Ski-off w Private Hot Tub & Sauna!
Oso Dream provides AMAZING panoramic views of Bear Mountain. Step out the front door and ski down Sundog trail to Sunrise Village Triple or step out the back door and hop onto Bear Cub trail to access Bear Mountain! Enjoy the amenities within the complex including indoor & outdoor heated pool (seasonal), sauna and gym. Guests also have access to the outdoor skating rink and xc ski trails (weather permitting). Free use of ice skates, puff hockey equipment, snow shoes, xc skies, poles and sleds!

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

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!

⭐️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.

Ski Back 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!

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.

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.

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 PERFECT WINTER RETREAT❄️ ⛷️ 🏂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 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 Chittenden rentals with a pool
House rentals with a pool

Epic Views of the Green Mountains

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

Ski On/Off Sunrise at Killington

Okemo Condo – Ski In/Out

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Dana Road House Sunlit VT Country Home w/HotTub

Killington Vistas: Luxury 4BR Ski On/Off. Hot Tub.

Comfortable, relaxing large country home
Condo rentals with a pool

1 BR Best Location w/ Pools/Massage Chair/Hottub!

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

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

Winterplace - Steps away from Slopes

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

Killington Getaway 2bed/1.5 bath

#45 Luxury Ski & Summer Condo with Private Sauna

Pleasantly Decorated with pool accessl C1
Other holiday rentals with a pool

Steps to Ski Lifts! Mountain Green Resort Retreat

Killington/Pico Condo, Cozy Family/Friend Getaway

Killington Vermont Luxury 2 bed condo

Perfect 2 Bedroom Ski in/out at Killington

Bright & Cozy Ski-in Condo with Mountain View

Empie's Igloo

Cozy Woods Resort and Spa Condo

Dream Catcher Farm
Quick stats about holiday rentals with a pool in Chittenden

Total holiday rentals
Explore 10 holiday rentals in Chittenden

Nightly prices starting at
Chittenden holiday rentals start at $342 AUD per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Chittenden holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chittenden rentals

4.9 Average rating
Chittenden stays are highly rated by guests—averaging 4.9 out of 5!
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Bolton Valley Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Montshire Museum of Science
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- Middlebury College
- Trout Lake
- Shelburne Vineyard
- Shelburne Museum
- Dartmouth College
- Southern Vermont Arts Center
- Quechee Gorge




