
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

Topridge 3BR w Incredible View & Private Hot Tub!
Oso Dream provides AMAZING panoramic views of Bear Mountain. Step out the front door and ski down Sundog trail to Sunrise Village Triple or step out the back door and hop onto Bear Cub trail to access Bear Mountain! Enjoy the amenities within the complex including indoor & outdoor heated pool (seasonal), sauna and gym. Guests also have access to the outdoor skating rink and xc ski trails (weather permitting). Free use of ice skates, puff hockey equipment, snow shoes, xc skies, poles and sleds!

Dog Friendly Mountain Condo w/Spa, Pool, Sauna
Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space. Pool and Spa area closed 5/4-5/15 for maintenance

Hotel Chic - Home Comfort -Ski Easy.
HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS OUR ULTRA COZY RETREAT WAITS JUST FOR YOU. MINUTES TO WEDDINGS, GRADUATIONS, HIKING, MOUNTAIN BIKING, GOLF, SEASONAL PRIVATE POOL. EASY ACCESS TO AT/LT. Pico-5 minutes Killington-15 minutes SUPERHOST RATED Air conditioned Fireplace, WIFI TV/living room & bedroom Adjustable queen bed Private covered porch Keypad check in Smoke free/Pet free Seasonal private pool NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.

Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

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 | Bike, Ski & Relax
In winter, you’re just 488 feet from the Sunrise lift. In summer, you’re minutes from one of the best mountain bike parks in the country, with the outdoor pool and hot tub reopening every Memorial Day. Sunrise Village is a true four-season resort, and this quiet, dog-friendly condo is one of its best spots. Whether you’re chasing powder days, peak foliage, long bike weekends, or just a few peaceful days in the mountains, the location does all the work.

Steps to Golf!
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!

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.

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
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.

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

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

Hilltop Hideaway 4 bed 3 bath, Eastman Lake

The Wheelock House- Family Home in Quechee

Updated Lake Cottage; 2 Min Walk to Lake

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

VT Country Club- 5bdr, Gameroom, Golf, Lake, Pool

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

The Fairway House - Premier Golf Course 3 BR Home
Condo rentals with a pool

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

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

Discounted rates; Now booking for Spring & Summer

Cozy Mountain Retreat w Views | Pool, Hot Tub, Ski

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

Still skiing Deal Cozy 2 Bedroom .2 mi to lift

One Bedroom Suite Near Okemo

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

Ski-in/out Jackson Gore Studio w/Kitchen

Sweet Retreat

Sophia's Place

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

Cozy, clean studio with picturesque Vermont views!

Jack Taylor Farm (with Alpacas & Inground Pool!)

Expansive dog friendly lakeview rental at Eastman

Skier's Retreat | Hot Tub | Sauna | Free Shuttle
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 $239 NZD per night before taxes and fees

Verified guest reviews
Over 110 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, 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 patio West Windsor
- Rentals with a fire pit West Windsor
- Rentals with outdoor seating West Windsor
- Rentals with a fireplace West Windsor
- Pet-friendly rentals West Windsor
- House rentals West Windsor
- Apartment rentals West Windsor
- Family-friendly rentals West Windsor
- Fitness-friendly rentals West Windsor
- Rentals with a washing machine and dryer West Windsor
- Rentals with pools Windsor County
- Rentals with pools Vermont
- Rentals with pools United States
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Pats Peak Ski Area
- Monadnock State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Dartmouth College
- Middlebury College
- Squam Lakes Natural Science Center
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Stinson Lake
- Southern Vermont Arts Center
- Warren Falls





