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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Guest favourite

Apartment in Killington

5 out of 5 average rating, 16 reviews

Modern Dog-Friendly/Wood-Burning Fireplace/Spa

This beautifully renovated, dog-friendly 2-BD, 2-BA home in The Woods offers a perfect blend of comfort and modern style. It features a spacious living area with a cozy wood-burning fireplace, a fully equipped kitchen, and exciting entertainment options, including an arcade game system and Xbox S gaming system. Just steps away, enjoy premium amenities such as an indoor pool, hot tub, and spa. Killington Café and Wine Bar next door provides the ideal spot to unwind—perfect for a relaxing retreat!

Superhost

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

Apartment in Killington

4.97 out of 5 average rating, 143 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

4.87 out of 5 average rating, 101 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

Home in Killington

4.97 out of 5 average rating, 89 reviews

Glamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Experience the charm and beauty of Killington like never before.

Guest favourite

Apartment in Stratton

4.98 out of 5 average rating, 43 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 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. 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.

Superhost

Cabin in Ludlow

4.73 out of 5 average rating, 11 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

Superhost

Apartment in Killington

4.6 out of 5 average rating, 95 reviews

NEW Killington Studio: Great Location! Comfy. 431

Welcome to our Killington studio, perfect for skiing, biking, hiking, antiquing, beer tasting, kayaking, exploring, or simply unwinding. This hotel room-style condo sleeps four in two comfortable queen beds. Enjoy cable/streaming on the large smart TV. Amenities include a mini-fridge, microwave, Keurig & coffee maker. The full bathroom offers a tub & shower. Outside, a heated pool awaits (open June to mid-September). You'll love it! (Note: This unit is hotel-room style without a kitchen.)

Guest favourite

Apartment in Killington

4.93 out of 5 average rating, 189 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, 138 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

Apartment in Stratton

5 out of 5 average rating, 12 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

Townhouse in Killington

4.96 out of 5 average rating, 104 reviews

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!