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

Total vacation rentals
Explore 20 vacation rentals in West Windsor

Nightly prices starting at
West Windsor vacation rentals start at ﺩ.ﺇ 514 per night before taxes and fees

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

Wi-Fi availability
20 of West Windsor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across West Windsor rentals

5 Average rating
West Windsor stays are highly rated by guests—averaging 5 out of 5!
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!

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!

Ski Mountain View Estate
Pool is open for the summer of '26 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. Great multi family getaway

Big Pool, Golf we are on the course 2 Bedroom
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!

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

Vermont Horse Farm
Enjoy a morning cup of coffee on the patio overlooking the horse pastures or an evening by a fire under the gazebo with a fire pit on this idyllic Vermont horse farm with glorious views. Close to many activities, such as hiking, skiing and swimming. Scenic retreat on a family owned and working farm. Here we have horses, donkey, chickens, goats, and of course our dogs and cats. There is a short hiking trail with beautiful views and a picnic table by the stream.

Golf and Mountain Biking outside the door!
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.

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!

AC | Dog-Friendly | Bike, Hike & Relax
Escape to the quieter side of Killington. Spring and summer are some of the best times to visit—fewer crowds, lower rates, and easy access to hiking, biking, golf, and everything the mountains have to offer. After a day outdoors, relax on the private balcony, unwind by the fireplace, or enjoy the resort amenities just minutes away.

Rocky Ledge: Cozy Pet-Friendly 3BR Log Cabin
Escape to Rocky Ledge, a pet-friendly 3-bedroom log cabin in Stoddard, NH. Perfect for groups of 6, this year-round retreat offers a cozy electric fireplace, high-speed internet, a full kitchen, a screen porch, and a large deck. Swim and canoe at the shared community pool & lakefront area. Your private, wooded adventure base awaits!
Popular amenities for West Windsor rentals with a pool
House rentals with a pool

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

Modern 3BR/3BA Main+River Retreat | Ski Okemo

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

Private Farmhouse with in ground pool!

Luxurious family retreat home in the mountains

Beautiful Okemo Farmhouse 0.7 mile from base lodge
Condo rentals with a pool

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

Serene 1-BR Ski-In/Ski-Out Retreat on Okemo Mtn.

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

Powder Hound - Modern, Heated Pool, BBQ, New Patio

One Bedroom Suite Near Okemo

Newly renovated ski retreat at Killington

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

Cozy condo within walking distance to the slopes.
Other vacation rentals with a pool

Relax&Play @ Tamarack House- Golf, Ski, Lake, Hike

Sweet Retreat

Cozy Cabin - Lake, Ski, Golf!

Sophia's Place

Cozy Mountain-style Condo by Okemo with a View!

Cozy Studio Apartment

Jack Taylor Farm (with Alpacas & Inground Pool!)

Five Bedroom Family Home on Okemo with A.C. splits
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- Pet-friendly rentals West Windsor
- House rentals West Windsor
- Family-friendly rentals West Windsor
- Rentals with a patio West Windsor
- Rentals with a fireplace West Windsor
- Rentals with a fire pit West Windsor
- Apartment rentals West Windsor
- Rentals with pools Windsor County
- Rentals with pools Vermont
- Rentals with pools United States
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Middlebury College
- Killington Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Mount Monadnock
- Squam Lakes Natural Science Center
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Stinson Lake
- Camp Plymouth State Park
- Warren Falls





