
Vacation 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!

Comfy ski in/out studio at base of Pico-Killington
Studio at the base of Pico with a balcony. Free shuttle service from my place to Killington, which is 10 minutes away.Brand new sofa bed with a pillow top. Room divider. Lots of TV channels with Xfinity. Luggage cart and elevator for easy access. Fast Wi-Fi. Free ski locker with one key for each guest. There is a laundry room with coin operated machines. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for one day. No daily cleaning service. No parties. Free parking

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!

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
The Suites at Killington is a 2RM/2BA suite in the heart of Killington. In the main suite, enjoy the open kitchen, dining and kitchen island, bathroom w/ tile shower, & cozy living area w/ sofa bed, queen bed, TV & patio. The primary bedroom offers a king/twin bed split, ensuite bathroom, TV, washer & dryer. Skiing or exploring, this suite offers a cozy retreat. Enjoy the heated pool (open June to mid-Sept). Unbeatable location with easy access to the best of Killington. Ski rental discounts.

Rocky Ledge at Highland Lake: Cozy 3BR Log Cabin
Nestled within the woods of Stoddard, NH, Rocky Ledge is a peaceful year-round family retreat. Our cozy log cabin has 3 bedrooms, 2 bathrooms, and a lower-level den perfect for family time. Enjoy outdoor dining on the large 3-sided deck, and cap off your days with s'mores sessions at the fire pit! Boating, hiking, swimming, and skiing are minutes away. Or, get cozy indoors and enjoy movies, puzzles, and games. Rocky Ledge is pet-friendly! We welcome up to two dogs with a flat $50 pet fee.

CozyCub - Pool, Hiking, Mountain Biking
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 C | AC | Sauna| Fireplace
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!

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!

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!

Cozy Condo- Close to Mountain, Ski home trail
Experience Killington like never before with our ski-home condo and a free 5min shuttle ride to the mountain on winter weekends. Our home is the perfect location to experience all that Killington has to offer. It has a free shuttle and a ski home trail. As well as quick and convenient access to Killington's great nightlife including restaurants, shopping, bars, and entertainment.
Popular amenities for West Windsor rentals with a pool
House rentals with a pool

Lake Pinneo, Golf View, Hot Tub - Tee Time Retreat

Fish, Bike, Golf, or Hike!

Modern 7-BR Chalet Minutes to Mt. Sunapee

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Dana Road House Sunlit VT Country Home w/HotTub

Peaceful condo at Okemo - Direct Ski Access

Private Farmhouse with in ground pool!

Luxurious family retreat home in the mountains
Condo rentals with a pool

Cozy Mountain Condo - Ski In/Ski Out

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Whiffletree base of Killington outdoor pool

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

Ski in Cozy 2 Bedroom only 1/2 mile to Mtn & Apres

Elegant 3BR with Fireplace & Shuttle to Slopes

#45 Luxury Ski & Summer Condo with Private Sauna

Stratton Duplex Condo Steps to Lifts, Village!
Other vacation rentals with a pool

Winter is upon us!

Ski-in Ski-Out Cozy Mountainside Condo

Ski-In/Ski-Out Hike Okemo Mountain Condo

Killington ski resort condo

The Fairway House - Premier Golf Course 3 BR Home

Charming Killington get away with pool, sleeps 4

Beautiful Lakeside home Eastman Lake; ski nearby

Premier Quechee Newton Village Condo: Pet Friendly
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.ﺇ514 per night before taxes and fees

Verified guest reviews
Over 120 verified reviews to help you choose

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

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 fire pit West Windsor
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- Rentals with a washer and dryer West Windsor
- Rentals with a patio West Windsor
- Rentals with a fireplace West Windsor
- Pet-friendly rentals West Windsor
- Apartment rentals West Windsor
- Rentals with pools Windsor County
- Rentals with pools Vermont
- Rentals with pools United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Dorset Field Club
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Hooper Golf Course
- Bromley Mountain Ski Resort
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Brattleboro Ski Hill
- Ekwanok Country Club
- Fox Run Golf Club