
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!

Lower Yurt Stay on VT Homestead
We are located in the hills of central VT, close to hiking, skiing and swimming. Disconnect to reconnect! Our homestead is based on permaculture landscape design. Unwind in the traditional Finnish Sauna, relax by the living pool, or kick back in an Adirondack chair looking out at the hills of VT. We have an ideal environment for digital detox. This is one of three listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay on VT homestead and Tiny house on VT homestead

Topridge 3BR w Incredible View & Private Hot Tub!
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!

Updated large condo across from AT and skiing
Family friendly, large 3 bedroom condo across the street from hiking and skiing in Killington. WiFi, cable TV, large gathering areas, spacious bedrooms, updated kitchen, and unlimited free firewood in winter. Plenty of après-ski chic touches make this a stylish yet comfortable retreat. 2 minute drive to Pico, 2 min walk to Appalachian Trail! Whether skiing, hiking, playing tennis, swimming, or game nights and cooking at-home meals with friends, this updated condo is a perfect spot to get away.

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. Pool and Spa area closed 5/4-5/15 for maintenance

105 Fox Hollow Village Pvt - Red Fox - Unit B-4
105 Fox Hollow Village is located near Pico and Killington ski areas. There are year round outdoor activities including access to trails for skiing/snowboarding, mountain biking, golfing, and hiking. Accommodations include 2 bedrooms, 2 full bathrooms (newly renovated), fully updated kitchen, living room, separate dining area, a mudroom at entrance, backyard access with sliding door, and a common pool area. No smoking/vaping, and no pets are allowed in or around the condo.

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)
Recently updated ski condo - modern kitchen appliances and new furniture. Minutes away from Killington Ski base. Drive there or use a paid bus service, steps away from the condo. Part of the luxurious Woods Spa Resort and stay includes use of resort amenities including gym, pool, steam/sauna and hot tub. Spa service available but not included in fee (please check for open hours) Warm, cozy and welcoming-custom built for ski lovers to relax after a long day on the mountains.

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.

Ski Basecamp with Pup • Sleeps 6 • Pool/Hot Tub
Comfortable, spacious condo perfect for families and small groups looking for an easy Killington getaway. Spread out after a day on the mountain with plenty of room to relax, a full kitchen for meals, and convenient access to Killington Resort and nearby activities. Ideal for ski trips, weekend getaways, or longer stays. ⭐ Walk to amenities: indoor pool, hot tub, steam room, and spa ✔ Great for families and groups ✔ Easy parking and access ✔ Close to slopes

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!

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.

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!
Popular amenities for Chittenden 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

3BR Ski on/off at Solitude/Okemo

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Dana Road House Sunlit VT Country Home w/HotTub

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

Best skiing in yrs; reduced rates

Winterplace - Steps away from Slopes

Serene Top Floor Condo (resort style amenities)

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

Amazing,Ski, Golf, Hike, Bike, Adventures

Green Mountain Basecamp | Minutes to Killington

Free Shuttle Route-Charming 3 BR 2 BA Ski Home/Off

Ski-In Luxe Chalet • Modern Retreat • 4BR Escape
Other holiday rentals with a pool

Newly renovated condo-The Woods

Sophia's Place

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

Cozy Slopeside Studio at Pico

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

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

Adventure Winter Ski & Spa Escape

Lake Bomoseen 2 BR Cottage
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 £81 per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Chittenden holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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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- Rentals with a fireplace Chittenden
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- Rentals with pools Rutland County
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- Rentals with pools United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Bolton Valley 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
- Adirondack Extreme Adventure Course
- Emerald Lake State Park
- Middlebury College
- Trout Lake
- Warren Falls
- Southern Vermont Arts Center
- Shelburne Museum




