
Holiday rentals with a pool in West Windsor
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in West Windsor
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 Mountain View Estate
Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Always plenty of firewood for the pit! Great multi family getaway

Historic Home on 17 acres of land. Go escape!
This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool will be reopened around May 2025 (weather dependent. It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything ask!

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.

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. check VRBO.1532508 mention this for a better deal

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!

Winterplace - Steps away from Slopes
Newly updated condo at Winterplace Okemo. This sunny corner 3 bedroom unit is just steps to the top of the A-B Quad. Completely renovated from floors to ceiling The delightful fireplace place will keep you toasty in the cozy living area. Outdoor ski locker just outside back door. Front door parking, and firewood included. Pool is open and available to renters all year. Hot tub in winter months and tennis courts in summer.

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails
Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

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.
Popular amenities for West Windsor rentals with a pool
House rentals with a pool

Stratton/Mt Snow minutes away! Hot tub + Game room

Pond, Pool, Mountain Views - Au Bout du Chemin

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

Premier Quechee Newton Village Condo: Pet Friendly

Dana Road House Sunlit VT Country Home w/HotTub
Condo rentals with a pool

Renovated unit, prime location! Shuttle on/Ski off

Cozy Slopeside Studio at Pico

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

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

Killington Getaway 2bed/1.5 bath

Cozy condo within walking distance to the slopes.

#45 Luxury Ski & Summer Condo with Private Sauna

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!
Other holiday rentals with a pool

Updated, Cozy Lake Cottage, 2 Min Walk to Lake

Luxury 3 BR Townhouse at The Castle Resort & Spa

Mount Ascutney 2 Bedroom

Cozy Ski-House by Okemo Hot Tub & Mountain Privacy

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

Cozy Mountain-style Condo by Okemo with a View!

Cozy Studio Apartment

6 Mi to Okemo! Family Townhome in Lakeside Resort
Quick stats about holiday rentals with a pool in West Windsor

Total holiday rentals
Explore 20 holiday rentals in West Windsor

Nightly prices starting at
West Windsor holiday rentals start at $242 NZD per night before taxes and fees

Verified guest reviews
Over 120 verified reviews to help you choose

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

Wi-Fi availability
20 of West Windsor holiday rentals include Wi-Fi access

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

4.9 Average rating
West Windsor stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a fireplace West Windsor
- House rentals West Windsor
- Rentals with pools Windsor County
- Rentals with pools Vermont
- Rentals with pools United States
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Crotched Mountain Ski and Ride
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Fox Run Golf Club
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- The Shattuck Golf Club
- Brattleboro Ski Hill
- Autumn Mountain Winery
- Northeast Slopes Ski Tow




