
Vacation rentals with a pool in Chittenden
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Chittenden

Total vacation rentals
Explore 10 vacation rentals in Chittenden

Nightly prices starting at
Chittenden vacation rentals start at ﺩ.ﺇ 404 per night before taxes and fees

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Over 950 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Chittenden vacation rentals include wi-fi 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!
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!

Hotel Chic - Home Comfort -Ski Easy.
HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS OUR ULTRA COZY RETREAT WAITS FOR YOU. MINUTES TO SEASONAL EVENTS, WEDDINGS, HIKING, MOUNTAIN BIKING, GOLF, PRIVATE POOL - JUNE/SEPT EASY ACCESS TO AT/LT. Pico-5 minutes Killington-15 minutes SUPERHOST RATED Air conditioned Fireplace, WIFI TV/living room & bedroom Adjustable queen bed Private covered porch Keypad check in Smoke free/Pet free Seasonal private pool NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children/pets.

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.

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Pool and Spa area closed May 4 to May 15 for annual Maintenance

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

Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
Ahoy, ski enthusiasts! "Jack S'Bearo" - a renovated 1-bed, 1-bath on Pico Mountain, VT, offers an exhilarating ski experience steps from the lift and a shuttle to Killington Resort. The new kitchen, wood-burning fireplace, and balcony make it a haven for relaxation. This ski on/ski off treasure boasts a cool design for easy access to the slopes. Grab your gear from the ski locker, step outside, and set sail to the lifts. Make "Jack S'Bearo" your pirate's cove, where adventure meets comfort!

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.

Bike park open Cozy 2 Bedroom .2 mi to mountain
Come enjoy this peaceful retreat, a warm fire and ski-in trail (depends on snowfall) with beautiful Mountain views! Our cozy 2 bedroom 1 bath is nestled away right on the golf course near Snowshed; Minutes away from ski lifts, restaurants and night life. Enjoy a warm space by the fire after skiing, snowmobiling, tubing and shopping! Shuttle every 30 min weekend & holiday weeks- Common laundry room -free washer/dryer Ski Locker- Pool heated in the summer Enjoy the Beast of the East!

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.
Popular amenities for Chittenden rentals with a pool
House rentals with a pool

Peaks, pool & pure mountain air — book for summer

Steps to Golf and Mountain Biking

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

Ski On/Off Sunrise at Killington

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

Killington Vistas: Luxury 4BR Ski On/Off. Hot Tub.
Condo rentals with a pool

2 Bedroom Pico/Killington Loft Condo at FoxHollow

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

Newly renovated ski retreat at Killington

Serene Top Floor Condo (resort style amenities)

Luxe Trailside Ski + Bike On/Off. Next to hot tub

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

#45 Luxury Ski & Summer Condo with Private Sauna

Amazing,Ski, Golf, Hike, Bike, Adventures
Other vacation rentals with a pool

Killington/Pico Condo, Cozy Family/Friend Getaway

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

Sweet Retreat

Sophia's Place

Beautiful Spacious Condo at Killington Resort

Green Mountain Basecamp | Minutes to Killington

Walk to lift, Ski home, Sunny with loft

Killington Ski Gateway Retreat | 2BR Condo
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- Rentals with a hot tub 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
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Killington Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Dartmouth College
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Middlebury College
- Bromley Mountain Ski Resort
- Adirondack Extreme Adventure Course
- Montshire Museum of Science
- Emerald Lake State Park
- Trout Lake
- Shelburne Vineyard
- Warren Falls
- Shelburne Museum





