
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.

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.

Hotel Chic - Home Comfort -Ski Easy.
HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS ❄️Killington - 15 minutes ❄️Pico - 5 minutes ❄️WIFI❄️QUIET❄️FIREPLACE ❄️COMFY❄️IMMACULATE ❄️SUPERHOST RATED OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️ 🏂Pico-5 minutes ⛷️ 🏂Killington-15 minutes 🥾Minutes from LT/AT 💍Wedding Venues 🚴Mtn Biking •Squeaky Clean •Fireplace, WIFI •TV in living room & bedroom •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.

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.

SKI ON/OFF Spruce Glen B | 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!

Beautiful rustic woods and fields retreat.
Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment/ mini house. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $50 per trip per dog

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.

One Bedroom Suite Near Okemo
This 675 square foot suite features a master bedroom with king bed and flat screen TV, separate living room with queen sleeper sofa, flat screen TV, and gas fireplace, full size kitchen, dining area, washer & dryer, and private bath with jetted tub. The Suites location in the Pointe hotel gives you access to the indoor pool, hot tub, fitness room and game room.

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace
Your group will be close to everything when you stay at this centrally-located condo. Enjoy two bedrooms plus a loft for a variety of sleeping options. Condo amenities include pool, gym, spa, tennis and hot tub. You will be close to the bars, restaurants, market and coffee shops and just minutes to the Killington resort base areas.
Popular amenities for West Windsor rentals with a pool
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

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

Fish, Bike, Golf, or Hike!

Ski-In/Ski-Out Hike Okemo Mountain Condo

Luxe 4BR w Incredible View & Game Room!

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Dana Road House Sunlit VT Country Home w/HotTub

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

Cozy Mountain Condo - Ski In/Ski Out

Renovated unit, prime location! Shuttle on/Ski off

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

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

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

Renovated 1BR, Walk to Lifts, Covered parking

Serene Top Floor Condo (resort style amenities)

#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

Villa with Pool + Fitness Center Access

Killington ski resort condo

Studio Condo: Shuttle. Close to Resort. Pool.

The Fairway House - Premier Golf Course 3 BR Home

Beautiful Lakeside home Eastman Lake; ski nearby

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 $181 SGD 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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- Pet-friendly rentals West Windsor
- Rentals with a firepit West Windsor
- Rentals with outdoor seating West Windsor
- Family-friendly rentals West Windsor
- Fitness-friendly rentals West Windsor
- Rentals with a patio 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
- Hildene, The Lincoln Family Home
- Dorset Field Club
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Hooper Golf Course
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Whaleback Mountain
- Northeast Slopes Ski Tow
- Brattleboro Ski Hill
- Ekwanok Country Club