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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.

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Home in Bridgewater

4.89 out of 5 average rating, 46 reviews

Luxurious family retreat home in the mountains

An exquisite newly renovated country retreat nestled between the mountains on 30 acres. Pond, open pasture and woodlands to explore. Indoor infrared sauna with red light therapy. Spa bathroom with freestanding tub and two rain water showers. Organic bedding. Grand fireplace. Large open concept kitchen with top of the line appliances and 14 stage drinking water filter. Movie theater. Kids space. 3 bedrooms + loft Killington Skyship Gondola - 7 minutes Okemo - 25 minutes Woodstock - 20 minutes

Chalet in Winhall

4.87 out of 5 average rating, 38 reviews

Vermont Cozy Chalet

Fully renovated Mountain Modern Luxury 3 bedroom, two and a half bath Chalet. Walking distance to Winhall and minutes to the ski trails. Winter, Spring, Summer, Fall this is your Vermont retreat. Whether you cool off in the pool in the Summer or come stay during Fall Foliage, this chalet invites you to relax. A newly installed pellet stove will keep you warm & toasty on winter nights. Enjoy this Green Mountain getaway, just 20 minutes to Manchester, or a perfect base for your day trips. No Pets.

Home in Londonderry

4.85 out of 5 average rating, 96 reviews

Comfortable home with a private indoor pool!

Ski & Ride Magic, Okemo, Stratton and Bromley! Our home is located on a quiet dead end road in the heart of Southern Vermont ski country! Great layout for entertaining. Perfect for 2 -3 families to gather. After a day in nature, no matter the season, enjoy a dip in the INDOOR HEATED POOL that stays 84 degrees all year round. BBQ meals on the deck and watch the sunset. Enjoy a nice fire on the patio or just cozy up to the pellet stove on colder nights. It will be vacation you'll always remember.

Guest favourite

Condo in Killington

4.98 out of 5 average rating, 138 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

3 bedroom townhouse with 2 full baths. Third bedroom is an open loft with 2 twin beds. The Woods is a luxury condo development located 3 miles from the lifts at Killington. Pool, gym and spa facilities. New for Winter 2024/25: Killington Cafe & Wine Bar at the The Woods! 6 guests max per law. ONE well-behaved DOG upon approval (NOT 2 DOGS); $90 pet fee per stay. *INCLUDE YOUR PET AS A GUEST AND TELL ME ABOUT YOUR DOG WHEN BOOKING. Sorry, NO CATS. Summer guests, NO A/C in the unit.

Guest favourite

Chalet in Winhall

4.88 out of 5 average rating, 100 reviews

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from the chaos of urban life and to decompress.How ? Enjoy the private and heated pool(until Sep15) during the day,and hang out by the outdoor fire pit when the sun is setting,and finish your evening off at the enclosed and brand new sea-salt hot tub!You will smell changes in the air as you drive through the trees,and you will hear the birds instead of the sirens when you are here.

Guest favourite

Condo in Stratton

4.97 out of 5 average rating, 39 reviews

A Village location, Steps to the Lifts & Village

Steps (literally) from the lifts & village, down the from the year-round heated pool, sauna & hot tubs This is one of the nicer units in Long Trail. Freshly painted throughout, comfy sofa & love seat in the living area, matching dishes glasses, it is super clean & well maintained. A 1-BR condo with King in the BR, Queen pullout couch in the LR, fully equiped kitchen, gas fireplace, indoor parking w/elevators, balcony w/ chairs, view overlooks the skating pond & mountains to the east.

Cabin in Ludlow

4.89 out of 5 average rating, 9 reviews

Contemporary 4-BR Cabin 5-min to Okemo

Contemporary, newly-renovated cabin perched on a hill overlooking the Green Mountains, 5-minutes to Okemo Base and 2-minutes in to town. Enjoy 4 bedrooms, atrium-style living room, separate dining room, breakfast nook, and basement game room. Grounds include a private pool, expansive yard, and sweeping views. Get the best of the traditional log cabin-feel with modern comfort and contemporary design; renovated in 2023 with AC and updated finishes throughout. Winter reservations: 4x4 required

Guest favourite

Condo in Killington

4.93 out of 5 average rating, 185 reviews

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

Guest favourite

Home in Plainfield

4.89 out of 5 average rating, 137 reviews

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! 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 just ask!

Guest favourite

Condo in Stratton

5 out of 5 average rating, 10 reviews

Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt

Rising Bear Duplex 411 at Stratton Mt-Seasonal Rental Available Spacious 3Br/4Bth Lodge on The Commons w/ Ice Skating Pond, Heated Pool, 2 Min Walk To Ski Family Friendly Spacious Lodge With Mountain Views, Excellent Location. Inspired by the great lodges, Rising Bear is located on the Commons, with ice skating, firepits and family activities. Convenient heated underground parking space and generous living spaces make Rising Bear ideal for bigger families and group gatherings.

Guest favourite

Home in Killington

4.98 out of 5 average rating, 80 reviews

Glamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in the serene Vermont landscape, invites you to indulge in a paradise of year-round adventure with breathtaking views of a picturesque pond. Ski, bike, hike amidst the foliage, ranked # 1 by Foliage Magazine. After your outdoor excursions, rejuvenate at the luxurious indoor pool and spa, pampering your senses like never before. Unwind by the cozy fireplace, create lasting memories and immerse yourself in Killington

Guest favourite

Condo in Killington

4.96 out of 5 average rating, 116 reviews

FirBear - Hot Tub, Pool, FirePlace, Gym

Revel in this bright and modern ski condo just off Killington's main road and close to everything. Relax after a day on the mountain streaming on one of your 3 smart TVs. Indulge with the fabulous condo amenities including the pool, hot tubs, spa, gym, and tennis courts, or settle in by the wood-burning fire. Spread out in this spacious condo and enjoy all that Killington has to offer. DISCOUNTED LIFT TICKETS AVAILABLE!

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Popular amenities for West Windsor rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Killington

4.91 out of 5 average rating, 190 reviews

Luxury Condo Tucked in the Heart of Killington

Guest favourite

Home in Mendon

4.88 out of 5 average rating, 231 reviews

Ranch at Mendon Mt Orchards

Home in Landgrove

4.75 out of 5 average rating, 28 reviews

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths!

Guest favourite

Home in Dorset

4.95 out of 5 average rating, 20 reviews

Idyllic Dorset Home: Serene Escape w/amazing views

Guest favourite

Home in Hartford

4.91 out of 5 average rating, 33 reviews

Bright & Modern Quechee Town House - Self Check-In

Guest favourite

Home in Hartland

5 out of 5 average rating, 10 reviews

Private Farmhouse with Pool

Home in Ludlow

4.77 out of 5 average rating, 43 reviews

Beautiful Okemo Farmhouse 0.7 mile from base lodge

Guest favourite

Home in Springfield

4.99 out of 5 average rating, 74 reviews

Luxury Mid-Century Modern Vermont Home, Okemo View

Condo rentals with a pool

Condo in Killington

4.84 out of 5 average rating, 75 reviews

Mountain Oasis

Guest favourite

Condo in Killington

4.92 out of 5 average rating, 111 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

Guest favourite

Condo in Killington

4.9 out of 5 average rating, 135 reviews

2 bed-2 bath (6 max): walk to lifts and lodges

Guest favourite

Condo in Killington

4.88 out of 5 average rating, 41 reviews

Killington Mnt 2Br/2Ba Ski/Golf/Bike/Hike/Pool

Condo in Killington

4.82 out of 5 average rating, 154 reviews

Skier's Retreat 2bed/1.5 bath condo w/ Amenities

Guest favourite

Condo in Killington

4.82 out of 5 average rating, 251 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

Condo in Killington

4.82 out of 5 average rating, 17 reviews

3 BR Ski-Home Condo!

Guest favourite

Condo in Killington

4.93 out of 5 average rating, 420 reviews

Slopeside Pico 1 bedroom 1 nite Ok free shuttle

Quick stats about holiday rentals with a pool in West Windsor

Total rentals
20 properties
Nightly prices starting at
$257 AUD before taxes and fees
Total number of reviews
110 reviews
Family-friendly rentals
10 properties are a good fit for families
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool

Destinations to explore