
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 ON/OFF Spruce Glen B | 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!

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.

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!

3BR Mt Green Condo Minutes from the Slopes!
Our 3 bed/2 bath unit is located within Mountain Green Resort, steps away from everything! Take the free shuttle to the resort and ski home! Mtn Green is undergoing roof replacements and interior work from fall 2024 to Fall 2025. Located next to Killington Golf Course, near Killington Adventure Center, and across the street from Killington Resort and the slopes of Snowshed Lodge. Sleeps up to 8 guests. Fully equipped kitchen and bath.

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.

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

Ski home to Trail Creek!

Ski-In/Ski-Out Hike Okemo Mountain Condo

Ranch at Mendon Mt Orchards

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Idyllic Dorset Home: Serene Escape w/amazing views

Premier Quechee Newton Village Condo: Pet Friendly

Dana Road House Sunlit VT Country Home w/HotTub

Farmhouse, Fireplace & Office - Wheelock Hideaway
Apartment rentals with a pool

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

Ski top 2 bottom Cozy 2 Bedroom .2 mi to the fun

Elegant 3BR with Fireplace & Shuttle to Slopes

Cozy Studio Condo on Bus Rte to Killington Resort!

Cozy condo within walking distance to the slopes.

Updated large condo across from AT and skiing

#45 Luxury Ski & Summer Condo with Private Sauna
Other holiday rentals with a pool

Mount Ascutney 2 Bedroom

Ski-in Ski-Out Cozy Mountainside Condo

Okemo - 15 mins; Hot Tub, Fire Pit, Pool Table

Killington ski resort condo

The Fairway House - Premier Golf Course 3 BR Home

Cozy, clean studio with picturesque Vermont views!

Cozy Studio Apartment

Peaceful condo at Okemo - Direct Ski Access
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 € 122 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 & child-friendly amenities

Wifi availability
20 of West Windsor holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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 firepit West Windsor
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- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Dartmouth Skiway
- Crotched Mountain Ski and Ride
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- Dorset Field Club
- Bromley Mountain Ski Resort
- The Shattuck Golf Club
- Autumn Mountain Winery
- Whaleback Mountain
- Mount Sunapee Resort
- Fox Run Golf Club
- Montshire Museum of Science




